US v. Rivera-Ruperto

Filing

OPINION issued by Juan R. Torruella, Appellate Judge; Kermit V. Lipez, Appellate Judge and Rogeriee Thompson, Appellate Judge. Published. TORRUELLA Circuit Judge, dissenting. [12-2364, 12-2367]

Case: 12-2364

Document: 00117105554

Page: 1

Date Filed: 01/13/2017

Entry ID: 6062260

United States Court of Appeals
For the First Circuit
Nos. 12-2364, 12-2367
UNITED STATES,
Appellee,
v.
WENDELL RIVERA-RUPERTO,
a/k/a Arsenio Rivera,
Defendant, Appellant.

APPEALS FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF PUERTO RICO
[Hon. Juan M. Pérez-Giménez, U.S. District Judge]

Before
Torruella, Lipez, and Thompson,
Circuit Judges.

H. Manuel Hernández for appellant.
Robert J. Heberle, Attorney, Public Integrity Section,
Criminal Division, U.S. Department of Justice, with whom Francisco
A. Besosa-Martínez, Assistant United States Attorney, Nelson
Pérez-Sosa, Assistant United States Attorney, Chief, Appellate
Division, and Rosa Emilia Rodríguez-Vélez, United States Attorney,
were on brief, for appellee.

January 13, 2017

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THOMPSON, Circuit Judge.

Entry ID: 6062260

This case arises out of a now-

familiar, large-scale FBI investigation known as "Operation Guard
Shack,"

in

which

the

FBI,

in

an

effort

to

root

out

police

corruption throughout Puerto Rico, orchestrated a series of staged
drug deals over the course of several years.1 For his participation
in six of these Operation Guard Shack drug deals, DefendantAppellant Wendell Rivera-Ruperto stood two trials and was found
guilty of various federal drug and firearms-related crimes.
convictions

resulted

in

Rivera-Ruperto

receiving

a

The

combined

sentence of 161-years and 10-months' imprisonment.
Although Rivera-Ruperto raises similar challenges in his
appeals from the two separate trials, each trial was presided over
by a different district judge.

Thus, there are two cases on

appeal, and we address the various challenges today in separate
opinions.2

In this present appeal from the first trial, Rivera-

Ruperto argues that the district court committed reversible errors
when it: (1) denied his claim for ineffective assistance of counsel
during the plea-bargaining stage; (2) failed to instruct the jury
that it was required to find drug quantity beyond a reasonable

1

See, e.g., United States v. Navedo-Ramirez, 781 F.3d 563
(1st Cir. 2015); United States v. González-Pérez, 778 F.3d 3 (1st
Cir. 2015); United States v. Diaz-Castro, 752 F.3d 101 (1st Cir.
2014).
2

Co-defendants Miguel Santiago-Cordero and Daviel SalinasAcevedo were tried along with Rivera-Ruperto at his second trial,
and we address their challenges in our companion decision as well.

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doubt; (3) either declined to consider or rejected his sentencing
manipulation

claim;

and

(4)

sentenced

him

to

a

grossly

disproportionate sentence in violation of the Eighth Amendment.
For the reasons stated below, we affirm the district
court.
OVERVIEW
We keep our summary of the facts brief for now, saving
the

specific

details

related

to

Rivera-Ruperto's

various

challenges for our later discussion.
Rivera-Ruperto

provided

armed

security

during

six

Operation Guard Shack sham drug deals, which occurred on April 9,
April 14, April 27, June 9, June 25, and September 16 of 2010.3
Each of the sham deals followed the same pattern.

They involved

undercover officers posing as sellers and buyers of fake cocaine,
and took place at FBI-monitored apartments wired with hidden
cameras. The April 9 and April 14 deals each involved 12 kilograms
of fake cocaine, the April 27 and June 9 deals each involved 8
kilograms of fake cocaine, and the June 25 and September 16 deals
each involved 15 kilograms of fake cocaine.

On top of rendering

armed security services, Rivera-Ruperto brought along with him

3

Although Rivera-Ruperto was not a police officer, he was
invited to participate in Operation Guard Shack after he
misrepresented himself to the FBI's confidential informant as a
prison corrections officer.

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additional recruits.4

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And at the April 27 deal, Rivera-Ruperto

did even more; he sold a handgun, including magazines, to a
confidential FBI informant posing as a drug dealer.

For his

services, Rivera-Ruperto received a payment of $2,000 for each of
the deals, except for the September 16 deal, for which he received
$3,000.
The
separate

government

indictments

(two

charged
on

Rivera-Ruperto

September

21,

2010

under
and

three
one

on

September 23, 2010) for his illegal participation in the six sham
drug deals.5

For each of the transactions, the indictments charged

Rivera-Ruperto with one count each of conspiracy and attempt to
possess with intent to distribute a controlled substance, as well
as possession of a firearm in relation to a drug trafficking crime.
Additionally, Rivera-Ruperto was charged with possessing a firearm
with an obliterated serial number during the April 27 deal.
Rivera-Ruperto's case proceeded to trial after plea
negotiations with the government failed -- a point of contention

4

Among those Rivera-Ruperto recruited, at least one was a
police officer.
5

On September 21, 2010, Rivera-Ruperto was indicted for his
participation in the April 14, April 27, June 9, and June 25, 2010
deals. On the same day, the government separately indicted RiveraRuperto for his participation in the April 9, 2010 deal.
Superseding indictments were later filed, but the charges remained
the same.
Rivera-Ruperto was then indicted a third time on
September 23, 2010 for his participation in the final September
16, 2010 deal.

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that we get to shortly. For purposes of trial, the first September
21 indictment (which charged Rivera-Ruperto for the April 14, April
27, June 9, and June 25 deals) and the September 23 indictment
(which charged him for the September 16 deal) were consolidated
and tried together.

A jury found Rivera-Ruperto guilty of all

charges and the district judge sentenced him to 126-years and 10months' imprisonment.

It is this first trial which is the topic

of the present appeal. As we discuss in more detail below, RiveraRuperto takes issue both with the judge's jury instructions and
with the sentence he ultimately received.
Over defense counsel's objections, the second September
21,

2010

indictment

(which

charged

Rivera-Ruperto

for

his

involvement in the transaction on April 9, 2010 only) was tried
several months later before a different district judge.

After a

second jury found Rivera-Ruperto guilty on all counts, RiveraRuperto received a 35-year sentence of imprisonment.
Rivera-Ruperto, who is presently serving his combined
sentence of 161 years and 10 months, now timely appeals.

Putting

aside, as we are required to do, whatever misgivings we might have
as to the need for or the wisdom in imposing a near two-life-term
sentence to punish a crime that involved staged drug deals, sham
drugs, and fake dealers, we turn to the task of assessing whether
any of Rivera-Ruperto's legal arguments entitle him to relief.

As

we have already noted, we address only Rivera-Ruperto's challenges

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from his first trial, saving those from the second for discussion
in our separate, related opinion.
DISCUSSION
I. Lafler Motion
Rivera-Ruperto first challenges the district court's
denial

of

his

claim

that

his

first

court-appointed

attorney

provided ineffective assistance at the plea-bargaining stage.

We

begin by recounting what happened below.
A.

Background
About a month after Rivera-Ruperto was arraigned, the

government made him an initial plea offer of 14 years that covered
the charged offenses in all three indictments.
first

court-appointed

attorney,

Jose

Rivera-Ruperto's

Aguayo

("Aguayo"),

successfully negotiated that offer down to 12 years.

When Rivera-

Ruperto refused to take the 12-year deal, Aguayo attempted to
negotiate an even lower sentence, but the prosecution told Aguayo
that its 12-year offer was final.
Aguayo

then

showed

Rivera-Ruperto

the

email,

which

spelled out the government's final offer of 12 years, and explained
to him the repercussions of not taking the plea deal.

But Rivera-

Ruperto rejected the offer still, and directed Aguayo to make a
counteroffer of 8 years instead.

Unsurprisingly, the government

refused the 8-year counteroffer.

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In a last-ditch effort, Aguayo joined defense attorneys
for five other Operation Guard Shack defendants to attempt to
negotiate a global plea deal for the six defendants as a group.
The government responded to these overtures by renewing its 12year offer for Rivera-Ruperto, but this time the offer had an
expiration date.

When Aguayo showed Rivera-Ruperto the renewed

offer, Rivera-Ruperto, once again, rejected it.
on February 4, 2011.

The offer lapsed

Accordingly, on February 7, 2011, the

government filed an informative motion, in which it notified the
court that plea negotiations had terminated and that a trial
schedule needed to be set.
On that same day, Aguayo, apparently alarmed by RiveraRuperto's

behavior

during

their

meetings

regarding

the

plea

negotiations, filed a request for a psychiatric exam for RiveraRuperto.

In the motion, Aguayo stated that during their meetings,

he had witnessed Rivera-Ruperto "exhibiting strange behavior which
has progressively worsened," and that Rivera-Ruperto "refuses to,
or lacks the ability to appreciate the seriousness of his case,
refuses to review the discovery material, appears to lose his
lucidity, rants and raves, and vehemently argues with imaginary
people in the attorney-client visiting room."

The district court

granted the motion by electronic order.
Shortly after being examined in early June 2011, RiveraRuperto sent Aguayo an email, in which he stated that he wanted to

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take the (by then, already expired) 12-year plea offer.

Aguayo

responded by advising Rivera-Ruperto that the 12-year deal had
timed out, and that they should await the results of the mental
evaluation before resuming further plea negotiations.

If he were

to withdraw the request for the psychiatric examination before
they saw the results, Aguayo explained, Rivera-Ruperto could later
argue, even after accepting an offer, that he had not been mentally
competent to accept it after all.
When the results of the psychological exam came back in
late June, the report deemed Rivera-Ruperto "stable" and contained
no

diagnoses

for

mental

disorders

that

Ruperto's competency to stand trial.6
reached

out

negotiations.
unwilling

to

to

the

government

to

would

affect

Rivera-

As promised, Aguayo then
attempt

to

reopen

plea

At first, it appeared the government would be
engage

in

further

plea

bargaining

with

Rivera-

Ruperto, whom the government believed had shown himself to be a
"malingerer."

But Aguayo was insistent that it was not Rivera-

Ruperto who had requested the psychological exam as a delay tactic,
but Aguayo himself who had requested it, compelled by his duty to
provide

Rivera-Ruperto

with

effective

assistance

of

counsel.

After some back and forth, the government relented and agreed to
entertain one, and only one more counteroffer from Rivera-Ruperto,

6

The report also suggested that Rivera-Ruperto may have been
exaggerating psychiatric impairment.

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but it warned that the counteroffer had to be "substantial"
(specifically, somewhere in the ballpark of 20-23 years).
Aguayo

met

with

Rivera-Ruperto

to

relay

this

information, making clear that this was their last chance to make
a counteroffer, and that a proposal of less than 20 years would
not be considered.

Despite this advice, Rivera-Ruperto insisted

that Aguayo make a counteroffer of only 13 years.

Unsurprisingly,

the government again rejected this lowball, but nevertheless made
one final offer of 18 years.
proceeded to fire Aguayo.

Rivera-Ruperto said no, and then

With plea negotiations over (this time

for good), the case was slated for trial.
On March 23, 2012, nine months after the date of the
psychological evaluation report and three days before trial was to
begin,

Rivera-Ruperto,

attorney,

filed

a

through

motion

his

alleging

second

that

court-appointed

Aguayo

had

provided

ineffective assistance of counsel at the plea-bargaining stage and
asking the district court to order the government to reoffer the
12-year deal.
for

an

The district court granted Rivera-Ruperto's request

evidentiary

hearing

on

the

issue

and,

after

hearing

testimony from both Rivera-Ruperto and Aguayo and considering the
documentary evidence,7 the district court concluded there was no

7

Although the documents themselves are not in the record,
the transcript from the Lafler hearing indicates that the parties'
submissions included email correspondence between Aguayo and the
government
regarding
plea
negotiations,
Aguayo's
records
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merit to the ineffective assistance of counsel claim, and denied
Rivera-Ruperto's motion.
B.

Rivera-Ruperto says this was error.

Analysis
We

review

a

district

court's

determination

of

ineffective assistance of counsel claims de novo and any findings
of fact for clear error.

Ortiz-Graulau v. United States, 756 F.3d

12, 17 (1st Cir. 2014).
A defendant's Sixth Amendment right to competent counsel
extends to the plea-bargaining process.
Ct. 1376, 1380-81 (2012).

Lafler v. Cooper, 132 S.

A defendant claiming, as Rivera-Ruperto

does here, that counsel's assistance was ineffective at the pleabargaining

stage,

must

meet

the

two-part

test

laid

Strickland v. Washington, 466 U.S. 668, 687 (1984).
S. Ct. at 1384.

out

in

Lafler, 132

He must show, first, that counsel's performance

was deficient, and second, that "the outcome of the plea process
would have been different with competent advice."
Rivera-Ruperto
prongs.

argues

that

he

meets

Id.
both

of

these

He contends that he "wanted to accept the 12-year plea

offer, and would have sans his original defense counsel's decision
to

seek

an

unnecessary

psychological

evaluation,

his

related

erroneous advice, and his refusal to inform the government and the

containing detailed notes of his visits and conversations with
Rivera-Ruperto,
and
a
document
signed
by
Rivera-Ruperto
memorializing his refusal to accept the government's original
"final" 12-year plea offer.

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district Court of [his] decision [to accept the 12-year offer]."8
But this argument fails on both Strickland requirements. To start,
Rivera-Ruperto has failed to establish that Aguayo's performance
was defective.
In order to meet the first Strickland prong, a defendant
must show that "counsel's representation fell below an objective
standard

of

reasonableness."

Strickland,

466

U.S.

at

688.

Generally speaking, "counsel is strongly presumed to have rendered
adequate assistance and made all significant decisions in the
exercise of reasonable professional judgment."

Id. at 690.

Thus,

in order to establish deficient performance, a defendant must show
that, "given the facts known at the time, counsel's choice was so
patently unreasonable that no competent attorney would have made
it."

Tevlin v. Spencer, 621 F.3d 59, 66 (1st Cir. 2010) (citing

Knight v. Spencer, 447 F.3d 6, 15 (1st Cir. 2006)).
Here, none of Aguayo's actions meets this standard.
Aguayo sought a psychological exam only after he observed RiveraRuperto
abnormal

arguing

with

behavior.

imaginary
While

people

ultimately

and

the

exhibiting

results

of

other

Rivera-

Ruperto's exam may have shown that Rivera-Ruperto did not have any

8

Rivera-Ruperto appears to limit his deficient-performance
argument to these bases, and does not challenge the district
court's finding that Aguayo otherwise competently made efforts to
get lesser plea deals for his client and adequately explained how
the plea bargaining process worked.

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mental health issues, given the erratic behavior Rivera-Ruperto
displayed during their meetings, Aguayo's motion was not "patently
unreasonable." Tevlin, 621 F.3d at 66 (citation omitted).9
Nor do we think Aguayo's performance was deficient on
account of the fact that he advised Rivera-Ruperto to await the
results of the psychological exam before pursuing further plea
negotiations.

First, as we get to in a moment, by the time Rivera-

Ruperto had emailed Aguayo to say he wished to take the 12-year
plea offer, there was no actual offer for Rivera-Ruperto to take
because the last 12-year deal had expired some three or four months
prior.

But even if there had been a live offer on the table, by

the time Rivera-Ruperto expressed any interest in taking a 12-year
plea deal, he had already been examined and was awaiting the
results.

As Aguayo explained to Rivera-Ruperto at the time, it

was Aguayo's professional judgment that withdrawing the motion for
the psychological exam at that point would threaten the durability
of any plea agreement they might have reached because RiveraRuperto could later argue that he had not been mentally competent
to enter into the deal at all.

We think this advice was given in

the exercise of reasonable professional judgment, and in any event,

9

In fact, "where there are substantial indications that the
defendant is not competent to stand trial, counsel is not faced
with a strategy choice but has a settled obligation . . . under
federal law . . . to raise the issue with the trial judge and
ordinarily to seek a competency examination." Robidoux v. O'Brien,
643 F.3d 334, 338-39 (1st Cir. 2011).

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certainly was not so deficient as to fall below "an objective
standard of reasonableness." Strickland, 466 U.S. at 688. RiveraRuperto has therefore failed to show that Aguayo's performance was
deficient.
Moreover,

even

if

we

were

to

assume

the

defective

performance prong has been met, Rivera-Ruperto's claim still fails
because he cannot show the necessary prejudice to meet the second
Strickland prong.

In order to establish prejudice, a defendant

claiming ineffective assistance at the plea bargaining stage must
show that "but for the ineffective advice of counsel there is a
reasonable

probability

that

the

plea

offer

would

have

been

presented to the court[,]. . . the court would have accepted its
terms, and that the conviction or sentence, or both, under the
offer's terms would have been less severe than under the judgment
and sentence."

Lafler, 132 S. Ct. at 1385.

Rivera-Ruperto cannot

do so here.
Rivera-Ruperto argues that he would have accepted the
12-year

deal

but

for

Aguayo

requesting

an

"unnecessary

and

unwanted" psychological exam and then refusing to withdraw the
request after Rivera-Ruperto told Aguayo that he wished to accept
the 12-year offer.

But the facts simply do not bear out Rivera-

Ruperto's theory that Aguayo's actions are what prevented a 12year plea deal from being presented to the court.

When Rivera-

Ruperto emailed to tell Aguayo that he wanted to take the 12-year

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plea offer, it was already early June 2011.

Entry ID: 6062260

By that time, nearly

four months had passed since the 12-year plea offer had expired.
It was therefore not the requested psychological examination that
caused Rivera-Ruperto to "lose" a 12-year plea deal, but the fact
that he had already rejected the offer (more than once, we might
add), leaving no deal on the table for Rivera-Ruperto to accept.
Furthermore,

even

after

the

results

came

back

from

Rivera-

Ruperto's psychological exam and the government had labeled him a
"malingerer," Rivera-Ruperto had a final opportunity to accept an
18-year plea offer from the government.
even this offer and opted for trial.

Rivera-Ruperto rejected
Rivera-Ruperto has thus

failed to show that there is a reasonable probability that any
plea deal, much less the 12-year plea deal specifically, would
have been presented to the court but for Aguayo's purported
ineffective assistance.
Because Rivera-Ruperto has failed to show that Aguayo's
performance was defective, and because, even if we were to assume
the performance was defective, Rivera-Ruperto has failed to show
the requisite prejudice, we affirm the district court's ruling on
the Lafler claim.
II. Jury Instructions
Rivera-Ruperto

raises

concerning the trial itself.

on

appeal

only

one

challenge

He argues that the district court

erred in failing to instruct the jury that it was required to make

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its drug quantity findings beyond a reasonable doubt.

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We begin

once more with a discussion of what happened below.
A.

Background
After closing arguments were made, the trial judge gave

jury instructions, beginning with general instructions, which
explained that the prosecution had the burden "to prove guilt
beyond a reasonable doubt."

The trial judge then instructed the

jury on the elements of the crimes with which Rivera-Ruperto was
charged.
As a reminder, among other charges, Rivera-Ruperto was
indicted for each of the five drug deals with one count each of
two drug crimes: conspiracy and attempted possession with intent
to distribute a controlled substance.

As they are the only

instructions relevant to our inquiry today, we focus our attention
on the judge's instructions regarding drug quantity.
The judge instructed the jury as to the elements of the
two drug offenses, and was explicit that in order to find the
defendant guilty, the jury had to be convinced that the government
had proven each element beyond a reasonable doubt.
not

include

drug

quantity

among

these

The judge did

elements,

but

after

explaining the elements of the drug crimes, the judge did tell the
jury: "If you find that the defendant conspired or attempted to
possess with intent to distribute a controlled substance[,] . . .
you will be asked to also make findings as to the quantity of this

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substance that the defendant either conspired or attempted to
possess."
The trial judge referred to drug quantity one other time
in his jury instructions.

This was when he described the verdict

forms to the jury, explaining: "[I]f you find [the] [d]efendant
guilty, then you are also asked to provide the amount of drugs
involved in said count.

And there's a question for you to find

that."10
Rivera-Ruperto's trial attorney raised no objections to
the jury instructions.

After deliberations, the jury returned a

verdict in which it found Rivera-Ruperto guilty of all charges.
With respect to the drug-related offenses, the jury found RiveraRuperto guilty "[i]n the amount of five kilograms or more" for
each of the counts, with the exception of the attempted possession
count for the September 16 deal, for which the jury did not return
a drug quantity finding.11

10

The verdict forms (there were two because there were
originally two indictments that were consolidated for trial) asked
the jury to mark whether it found Rivera-Ruperto "Guilty" or "Not
Guilty" for each of the charged counts.
Underneath the drug
related counts, the verdict form asked the following question:
If you find the defendant guilty, please answer the
following additional question:
Do you find that the amount of fake cocaine involved
in that offense was (circle one):
A. 5 kilograms or more
B. At least 500 grams but less than 5 kilograms
C. Less than 500 grams
11

Although the jury found Rivera-Ruperto guilty of that
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At sentencing, the district court imposed a sentence for
these drug convictions that was based on the jury's drug quantity
findings.

Specifically, because the jury had found that all of

Rivera-Ruperto's drug offenses (except the September 16 attempted
possession count) involved 5 kilograms or more of a controlled
substance, the court imposed concurrent sentences of 21-years and
10-months' imprisonment for each of these convictions.12

The

sentences thus exceeded the 20-year statutory maximum for offenses
involving an indeterminate quantity of drugs, see 21 U.S.C. §
841(b)(1)(C), and instead fell within the minimum 10-year to
maximum life sentencing range for offenses involving 5 kilograms
or more of a controlled substance, id. § 841(b)(1)(A).
On appeal, Rivera-Ruperto argues that he is entitled to
a new trial because the district court failed to instruct the jury
that

it

was

required

to

find

the

drug

quantities

beyond

a

reasonable doubt.
B.

Analysis
We typically review jury instruction challenges de novo,

but where, as here, a defendant failed to object to the jury

count, it left the corresponding drug quantity question blank on
the verdict form.
12

For the September 16 attempted possession conviction, for
which the jury had returned no drug quantity finding, the district
court imposed the maximum statutory sentence of 20 years for
offenses involving an indeterminate quantity of drugs.
See 21
U.S.C. § 841(b)(1)(C).

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instructions below, our review is for plain error.

Entry ID: 6062260

United States

v. Delgado-Marrero, 744 F.3d 167, 184 (1st Cir. 2014).
Reversal

under

the

plain

error

standard

requires:

(1) that an error occurred; (2) that the error was obvious;
(3) that it affected the defendant's substantial rights; and
(4) that it threatens the fairness, integrity or public reputation
of the proceedings.

Delgado-Marrero, 744 F.3d at 184.

We have

noted previously that "[t]his multi-factor analysis makes the road
to success under the plain error standard rather steep; hence,
reversal constitutes a remedy that is granted sparingly."

United

States v. Gelin, 712 F.3d 612, 620 (1st Cir. 2013).
We begin with the question of error.

To satisfy plain

error review, we must conclude not only that the district court
erred in not instructing the jury that it was required to find
drug quantity beyond a reasonable doubt, but that the error was
obvious.
The Supreme Court has held that facts such as drug
quantity are to be considered elements of the offense and must be
found beyond a reasonable doubt if those facts "increase the
penalty for a crime beyond the prescribed statutory maximum,"
Apprendi v. New Jersey, 530 U.S. 466, 490 (2000), or increase the
mandatory minimum sentence for a crime, Alleyne v. United States,
133 S. Ct. 2151 (2013).

In this case, it is clear that drug

quantity was an element of Rivera-Ruperto's charged drug offenses

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because the drug quantity findings increased Rivera-Ruperto's
sentence

beyond

quantities.

the

statutory

maximum

for

undetermined

drug

At trial, the judge did submit the drug quantity

question to the jury, and also instructed the jury that the
government was required to prove each element of the drug offenses
beyond a reasonable doubt.

But he never instructed the jury that

drug quantity was an element of the drug crimes, nor did he ever
state explicitly that drug quantity had to be found beyond a
reasonable doubt.

The question we must answer, then, is whether

the jury nonetheless would have understood that it was required to
apply the beyond-a-reasonable-doubt standard to its findings on
drug quantity.

We conclude that it did, and that the court

therefore did not commit obvious error.
In United States v. Barbour, 393 F.3d 82, 89 (1st Cir.
2004), a case involving similar facts, the district court failed,
much like the court in this case, to instruct the jury that drug
quantity was an element of the offense, although it should have
done

so.

constitute

We

concluded,

obvious

error

however,
because

that
the

this

jury

failure

had

been

did

not

"clearly

instructed that the defendant's guilt must be proven beyond a
reasonable doubt" and subsequently told, albeit separately, that,
if the jury found the defendant guilty, it would be required to
make

a

drug

quantity

finding.

Id.

We

reasoned

that

the

instructions, while not perfect, sufficiently "connected that

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burden of proof to the drug quantity determination."

Id.

In

addition, as in the present case, the verdict form contained a
multiple-choice drug quantity question that immediately followed
the question regarding the defendant's guilt.
circumstances,

we

concluded

committed plain error.

that

the

Id.

district

Under those

court

had

not

Id.

Likewise, here, although the judge never instructed the
jury that it was required to make its drug quantity findings beyond
a

reasonable

correctly

doubt

submitted

(though,
the

we

drug

stress,

quantity

he

should

question

to

have),
the

he

jury,

instructed the jury more than once as to the government's beyonda-reasonable-doubt burden, and instructed the jury that if it found
Rivera-Ruperto guilty of a drug offense, it would also be required
to make a drug quantity finding. Furthermore, on the verdict form,
after each question that asked whether the jury found RiveraRuperto "guilty" or "not-guilty" of a drug-related offense, a
question directing the jury to make a multiple-choice finding as
to drug quantity immediately followed.

Thus, the "link between

the burden of proof and the jury's quantity determination," id. at
89, was at least as close here as it was in Barbour.
In arguing that the district court nonetheless committed
plain error, Rivera-Ruperto relies on Delgado-Marrero, a case in
which, applying plain error review, we remanded for resentencing
on the basis of an Alleyne error. 744 F. 3d at 186-90. In Delgado-

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Marrero, however, the district court had submitted drug quantity
to the jury as a special verdict question only after the jury had
already deliberated and returned its guilty verdict.

Id. 186-87.

The court never directed the jury to apply the beyond-a-reasonabledoubt standard to the special verdict question, nor did it instruct
the jury that drug quantity was an element of the drug offense.
Id. at 187.

Under those circumstances, "given the timing and

manner in which the [drug quantity] question was presented," we
reasoned that we could not find that the jury was "sufficiently
put on notice of [the drug quantity question's] critical import to
this case."

Id.

Because the jurors "had no cause to understand

the special verdict question as involving another element of the
offense," we concluded that the court had obviously erred.
By

contrast,

here,

as

we

have

already

noted,

Id.
drug

quantity was submitted to the jury in the initial jury instructions
and on the verdict form, and the court explicitly instructed the
jury that the government was required to prove its case beyond a
reasonable doubt.

Therefore, Rivera-Ruperto has not cleared the

obvious-error hurdle.
Moreover, even if we assumed that the district court's
error was obvious and that it affected the defendant's substantial
rights,13 reversal still would not be warranted because Rivera-

13

drug

For all but one of Rivera-Ruperto's convictions, the jury's
quantity finding triggered enhanced mandatory minimum
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Ruperto cannot show that the error was sufficiently fundamental to
threaten the fairness, integrity, or public reputation of the
proceedings.

See id. at 184.

The evidence in this case that each

of the staged drug deals involved more than 5 kilograms of sham
cocaine was "overwhelming" and "essentially uncontroverted," which
gives us no basis for concluding that the judicial proceedings
were so affected.

United States v. Cotton, 535 U.S. 625, 633

(2002) (holding that the fourth plain-error-review requirement
cannot be met where the evidence of an element was "overwhelming"
and "essentially uncontroverted" at trial) (quoting Johnson v.
United States, 520 U.S. 461, 470 (1997)).
At trial, the government showed the jury video footage
from each of the charged drug deals of a confidential informant
weighing the bricks of sham cocaine, and then Rivera-Ruperto
placing

each

brick

into

a

suitcase.

The

same

confidential

informant also testified on the stand as to the number of kilograms
of sham cocaine that were used during each deal.

No conflicting

evidence emerged at trial that might have possibly called into
question the government's drug quantity evidence, and RiveraRuperto does not provide any argument on appeal as to how we might

sentences and resulted in sentences that exceeded the statutory
maximum sentence for undetermined drug quantities. Thus RiveraRuperto's substantial rights would have been affected had the jury
instructions been obviously erroneous, and Rivera-Ruperto would
have met plain error review's third prong.

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conclude that, given the evidence presented, any error on the
district

court's

part

threatened

the

fairness,

integrity,

or

public reputation of his trial.
Let us be clear: we think the district court's jury
instructions were flawed, and that the judge should have instructed
the jury that it was required to make its drug quantity findings
beyond

a

reasonable

doubt.

But,

as

Rivera-Ruperto

has

not

succeeded in climbing the steep road of plain error review, we
cannot reverse.
III. Sentencing Challenges
Rivera-Ruperto's remaining two arguments are challenges
to his sentence. He argues that the government engaged in improper
sentencing manipulation when it set up the sting operation, and
also that his resulting combined sentence between the two trials
of

161

years

and

10

months

violated

the

prohibition on cruel and unusual punishment.

Eighth

Amendment's

We begin for a final

time by recounting what happened below.
A.

Background
At the beginning of Rivera-Ruperto's sentencing hearing,

defense

counsel

raised

the

issue

of

sentencing

manipulation,

arguing that the FBI had arbitrarily chosen to use "large" amounts
(more than 5 kilograms) of sham cocaine for the sole purpose of
enhancing Rivera-Ruperto's sentencing exposure.

Defense counsel

argued that, for each of the staged drug transactions, the elements

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of the charged offenses would have been fulfilled with lesser
amounts of sham cocaine, and that the FBI's decision to use the 8kilogram, 12-kilogram, and 15-kilogram quantities could only have
been for purposes of "mere sentencing enhancement."
Defense
charging

counsel

practices

also

argued

constituted

that

the

government's

impermissible

sentencing

manipulation because the series of five drug deals could have been
charged as a single drug conspiracy, in which case Rivera-Ruperto
would have been convicted of just one count of possession of a
firearm in violation of 18 U.S.C. § 924(c), an offense that carries
with it a mandatory minimum sentence of 5 years imprisonment, id.
§ 924(c)(1)(A).

Instead, the government chose to charge each drug

deal as a separate transaction, counsel contended, fully knowing
that each "second or subsequent" conviction under the subsection
carries

with

imprisonment,

it
id.

a

mandatory
§

minimum

924(c)(1)(C)(i),

consecutively, id. § 924(c)(1)(D)(ii).

sentence
which

of

must

25
be

years
served

As a result, Rivera-

Ruperto's sentencing exposure in the first trial was 105-years
imprisonment for the firearms convictions alone.
The government argued that there had been no improper
conduct on its part.

Each staged drug deal had in fact been a

separate event, involving varying amounts of sham cocaine.

And

Rivera-Ruperto had decided each time to participate voluntarily,
without regard to the amount involved.

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After

hearing

Page: 25

from

both

Date Filed: 01/13/2017

sides,

the

Entry ID: 6062260

district

court,

without making an explicit ruling on the sentencing manipulation
argument, imposed the following sentence.

For all but one of the

drug convictions, the district court sentenced Rivera-Ruperto to
concurrent 21-year and 10-month terms of imprisonment.14

For the

remaining attempted possession conviction (for which the jury had
not returned a drug quantity finding), the district court sentenced
Rivera-Ruperto to a term of 20 years (the statutory maximum where
the amount of drugs involved is undetermined).

The district court

also sentenced Rivera-Ruperto to 5-years imprisonment for his
conviction for possession of a firearm with an obliterated serial
number during the April 27 drug deal.

This 5-year sentence was to

run concurrently with the 21-year-and-10-month and 20-year drug
sentences.
As for the other firearms counts, the district court
imposed a 105-year sentence based on the mandatory 5-year minimum
term for the first conviction under 18 U.S.C. § 924(c), and four
consecutive
subsequent

25-year
§

924

mandatory

convictions.

minimum
In

14

terms

total,

for

the

Rivera-Ruperto

four
was

Reminder: the jury convicted Rivera-Ruperto of one count
of conspiracy and one count of attempted possession for each of
the five drug deals, and found for each count (except for the
September 16 attempted possession count) that 5 kilograms or more
of sham cocaine were involved.

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sentenced to 126-years and 10-months' imprisonment from the first
trial.
Rivera-Ruperto was then also convicted of all counts at
his second trial, and the second judge imposed a sentence of 35years

imprisonment,

sentence.

to

be

served

consecutively

to

his

first

This brought Rivera-Ruperto's combined sentence for his

participation in six fake drug deals to 161-years and 10-months'
imprisonment.
Rivera-Ruperto now appeals the sentencing manipulation
issue and raises an Eighth Amendment challenge to the total length
of his sentence.
B.

Sentencing Manipulation
Sentencing factor manipulation occurs "where government

agents have improperly enlarged the scope or scale of [a] crime."
United States v. Lucena-Rivera, 750 F.3d 43, 55 (1st Cir. 2014)
(alteration in original) (quoting United States v. Fontes, 415
F.3d 174, 180 (1st Cir. 2005)).

Where the government engages in

such manipulation, we "recognize[] the court's power to impose a
sentence below the statutory mandatory minimum as an equitable
remedy."

Fontes, 415 F.3d at 180.
Rivera-Ruperto begins his sentencing manipulation appeal

by arguing that the district court neglected to address his
properly-raised sentencing manipulation objection at all, and that

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this alone constitutes clear error and warrants reversal.

We

address this threshold argument first.
It

is

true

that

the

sentencing

hearing

transcript

reflects that the district court never made an explicit ruling on
Rivera-Ruperto's sentencing manipulation objection.

However, the

transcript also plainly indicates that at the hearing, the judge
invited defense counsel to make any statements he wished.

After

defense counsel argued the sentencing manipulation issue, the
judge thanked him, acknowledging that he had heard the argument,
and then, after allowing Rivera-Ruperto himself to speak, invited
the government to respond.

The judge gave the government ample

time to argue the sentencing manipulation issue as well, and then
thanked the government lawyer before imposing the sentence.
Based on the transcript, we think it evident that the
judge effectively denied the sentencing manipulation objection
when he chose not to deviate from the statutory minimums in
sentencing Rivera-Ruperto for his crimes.

This appears to have

been clear enough to defense counsel as well, because counsel
raised no objection and asked for no clarification as to the
judge's ruling on the sentencing manipulation issue, even when the
judge invited counsel to speak after he imposed the sentence.15

15

In

The judge asked, "That is the sentence of the Court.
Anything else, Counsel?" Defense counsel responded by requesting
abatement for the special monetary assessment (which the judge
granted), but did not bring up the sentencing manipulation issue
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the face of such an extraordinary sentence, the district court
should have taken the time to explain why it concluded that the
doctrine of sentencing factor manipulation did not warrant relief,
rather

than

inferences,

leave
but

it

for

we

this

court

nevertheless

to

draw

conclude

the

that

necessary
the

judge

effectively denied Rivera-Ruperto's sentencing manipulation claim,
and we turn to its merits.
Because
manipulation

in

"[b]y
any

definition,

sting

there

operation,"

we

is

an

element

reserve

relief

of
for

sentencing factor manipulation only for "the extreme and unusual
case," Lucena-Rivera, 750 F.3d at 55 (alteration in original)
(quoting Fontes, 415 F.3d at 180), such as those situations
"involving outrageous or intolerable pressure [by the government]
or illegitimate motive on the part of the agents," United States
v. Navedo-Ramirez, 781 F.3d 563, 580 (1st Cir. 2015) (alteration
in original) (quoting United States v. Richardson, 515 F.3d 74, 86
n.8 (1st Cir. 2008)).

It is the defendant who bears the burden of

establishing sentencing factor manipulation by a preponderance of
the evidence, and a district judge's "determination as to whether
improper

manipulation

exists

is

ordinarily

determination subject to clear-error review."
Gibbens, 25 F.3d 28, 30 (1st Cir. 1994).

again.

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Here, Rivera-Ruperto argues, as he did below, that the
government

engaged

in

sentencing

manipulation

by

using

unnecessarily high quantities of sham drugs during the deals, by
requiring Rivera-Ruperto to bring a firearm with him to each of
the deals, and then by allowing him to participate in a "seemingly
endless" number of those deals.16

The government's only reason for

structuring the sting operation in this way, he says, was to
inflate his eventual sentence.
But Rivera-Ruperto has not met his burden to show by a
preponderance of the evidence that the government's motivations
were indeed improper.

At trial, FBI agents testified that the

government used large quantities of sham cocaine for the purpose
of ensuring that the staged deals looked realistic enough to
warrant the need for armed security.

Although it is certainly

feasible that, as Rivera-Ruperto argues, the agents could have
used some lesser quantity of drugs and still made the deals look

16

In his brief, Rivera-Ruperto appears not to reprise the
argument, which he raised below, that the prosecution's charging
practices (specifically, its decision to charge the five drug deals
separately as opposed to as a single conspiracy) constituted
impermissible sentencing manipulation. To the extent that counsel
alluded to this issue at oral argument, absent exceptional
circumstances, we generally consider as waived issues raised only
at oral argument. See United States v. Vazquez-Rivera, 407 F.3d
476, 487-88 (1st Cir. 2005).
And even if we were to make an
exception here, counsel has provided no evidence that the
government was driven by improper motives in charging the drug
transactions, which occurred on separate days and involved
distinct drug deals, as separate conspiracies.

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realistic, the mere fact that they did not, without more, does not
establish that the agents engaged in the kind of "extraordinary
misconduct," United States v. Sánchez-Berríos, 424 F.3d 65, 78-79
(1st Cir. 2005), that is required of a successful sentencing
manipulation claim.
Likewise, it was a part of the sting operation's design
from the get-go that Operation Guard Shack would "hire" corrupt
law enforcement officers to provide armed security at the staged
drug deals, and that those officers would then, in turn, be asked
to recruit others to participate in subsequent deals, thereby
unwittingly

assisting

corrupt officers.17

the

sting

in

ferreting

out

additional

Rivera-Ruperto has provided no evidence to

suggest that, in telling him to bring a firearm to the deals or in
allowing him to participate in multiple deals, the FBI agents
engaged in "anything beyond the level of manipulation inherent in
virtually any sting operation" or "lure[d] the appellant[] into
committing

crimes

more

heinous

than

[he

was]

predisposed

to

commit." Sánchez-Berríos, 424 F.3d at 79.
Moreover,

these

same

arguments

have

already

attempted and lost by other Operation Guard Shack defendants.

17

been
See

As we have already noted, Rivera-Ruperto was not himself a
police officer (and turned out not even to be a prison corrections
officer, as he had originally claimed), but among those codefendants that he recruited to participate in subsequent
Operation Guard Shack deals, at least one was an officer in the
Puerto Rico Police Department.

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Navedo-Ramirez, 781 F.3d at 570 (denying defendant's argument that
government's use of high drug quantities constituted sentencing
factor manipulation); Lucena-Rivera, 750 F.3d at 55 (rejecting the
defendant's

argument

that

the

government

had

prolonged

its

investigation for a year in order to inflate the sentence, where
the government argued that it had done so to identify other
conspirators,

and

the

defendant

did

not

otherwise

present

sufficient evidence of an improper motive); Sánchez-Berríos, 424
F.3d at 78-79 (denying defendant's argument that the government
connived to make him bring his firearm to the deal in order to
enhance his sentencing exposure).
did

not

clearly

err

in

The district court therefore

denying

Rivera-Ruperto's

sentencing

manipulation claim.
C.

Eighth Amendment
Rivera-Ruperto's final argument on appeal is an Eighth

Amendment challenge to his sentence.

Rivera-Ruperto argues that

his combined sentence between the two trials for 161-years and 10months' imprisonment constitutes cruel and unusual punishment.

We

assume, favorably to Rivera-Ruperto, that this Eighth Amendment
argument was properly preserved, and review his challenge de
novo.18

18

The government makes no argument whatsoever in its brief
in this first appeal as to what standard of review applies, but it
argues in its brief in Rivera-Ruperto's second appeal that RiveraRuperto's Eighth Amendment claim was not properly preserved below,
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Let us begin by acknowledging that Rivera-Ruperto's 161year and 10-month sentence is indeed extraordinarily long.

But in

order

Eighth

to

deem

it

constitutionally

infirm

under

the

Amendment's cruel and unusual punishment clause, there are three
criteria we must assess: "(i) the gravity of the offense and the
harshness of the penalty; (ii) the sentences imposed on other
criminals in the same jurisdiction; and (iii) the sentences imposed
for commission of the same crime in other jurisdictions."

United

States v. Polk, 546 F.3d 74, 76 (1st Cir. 2008) (quoting Solem v.
Helm, 463 U.S. 277, 292 (1983)).

We reach the last two criteria

only if we can first establish that the sentence, on its face, is
grossly disproportionate to the crime.

Id.

To quickly sketch out the underpinnings for RiveraRuperto's sentence once more, of the combined 161 years and 10
months to which Rivera-Ruperto was sentenced, the lion's share of

and that plain error review applies. For his part, Rivera-Ruperto
does not discuss the standard of review in either opening or reply
brief in either appeal.
On our read of the record, at least when it comes to his first
sentence, Rivera-Ruperto probably did enough to preserve an Eighth
Amendment challenge. At the first sentencing hearing after the
first trial, counsel for Rivera-Ruperto argued that the prescribed
statutory minimums had resulted in a punishment that "goes way
over, substantially way over, what's necessary for punishing these
offenses," and resulted in a "horribly, horribly increased
sentence which borderlines on draconian." No similar arguments
were made at Rivera-Ruperto's second sentencing, but for our
purposes today, we will apply the defendant-friendly de novo
standard to Rivera-Ruperto's challenge to his combined sentence.

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the sentence -- 130 years to be exact -- was the result of minimum
sentences required by statute for Rivera-Ruperto's six firearms
convictions under 18 U.S.C. § 924(c)(1)(C) (5 years for his first
§ 924 conviction, and 25-year consecutive sentences for each of
the five subsequent convictions).19

Because Rivera-Ruperto bases

his Eighth Amendment challenge on the length of his sentence in
its totality, in order to prevail, he must establish that this
statutorily-mandated 130-year sentence is grossly disproportionate
on its face.20

Thus, we focus our inquiry here on the portion of

his sentence stemming from the § 924(c) convictions.
In noncapital cases, the Eighth Amendment "does not
require a precise calibration of crime and punishment."
States v. Graciani, 61 F.3d 70, 76 (1st Cir. 1995).

United

Rather, "[a]t

most, the Eighth Amendment gives rise to a 'narrow proportionality
principle,'

forbidding

only

extreme

sentences

that

are

significantly disproportionate to the underlying crime."

Id.

(quoting Harmelin v. Michigan, 501 U.S. 957, 997 (1991) (Kennedy,
J.)).

We have previously remarked that "instances of gross

19

As for the rest of Rivera-Ruperto's term of imprisonment,
as we have already explained, 21 years and 10 months of the
sentence were the result of all the remaining convictions from the
first trial, and 10 years of the sentence were from the remaining
convictions from the second trial.
20

In other words, Rivera-Ruperto does not argue that we could
somehow find that the remaining 31 years and 10 months resulting
from his other convictions were, by themselves, grossly
disproportionate to the crimes for which they were imposed.

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disproportionality will be hen's-teeth rare."
76.

Entry ID: 6062260

Polk, 546 F.3d at

The Supreme Court has upheld against disproportionality

challenges, for example, a sentence of 25 years to life under
California's "three strikes law" for the theft of golf clubs, Ewing
v. California, 538 U.S. 11, 30-31 (2003), and a sentence of 40
years for possession with intent to distribute nine ounces of
marijuana, Hutto v. Davis, 454 U.S. 370, 370-74 (1982) (per
curiam).
The dissent here argues that in those cases where the
Supreme Court has upheld harsh sentences for seemingly minor
crimes, the Court's rationale was justified because the offenders
were recidivists and recidivism is a legitimate basis on which a
legislature can elect to sentence more harshly.

However, we see

no reason why recidivism may be deemed such a legitimate basis,
but crimes involving the combination of drugs and weapons -- like
those targeted by the § 924(c) stacking regime -- may not also be
deemed a legitimate basis.

To the contrary, "[t]he Supreme Court

has noted that the 'basic purpose' of § 924(c) is 'to combat the
dangerous combination of drugs and guns'" and "has also noted that
'the provision's chief legislative sponsor . . . said that the
provision seeks to persuade the man who is tempted to commit a
Federal felony to leave his gun at home.'"

United States v.

Angelos, 433 F.3d 738, 751 (10th Cir. 2006) (quoting Muscarello v.
United States, 524 U.S. 125, 126 (1998)).

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Defendants have a particularly difficult time passing
through the proportionality principle's narrow channel where the
sentence is the result of a statutory mandate.

This is because

courts are required to give deference to the judgments of the
legislature in determining appropriate punishments, and must "step
softly and cede a wide berth to the Legislative Branch's authority
to match the type of punishment with the type of crime."

Polk,

546 F.3d at 76; see also Harmelin, 501 U.S. at 998 ("[T]he fixing
of

prison

terms

for

specific

crimes

involves

a

substantive

penological judgment that, as a general matter is 'properly within
the province of legislatures, not courts.'" (quoting Rummel v.
Estelle, 445 U.S. 263, 275-76 (1980)).

Accordingly, "[n]o circuit

has held that consecutive sentences under § 924(c) violate the
Eighth Amendment."

United States v. Robinson, 617 F.3d 984, 991

(8th Cir. 2010) (alteration in original) (quoting United State v.
Wiest, 596, F.3d 906, 912 (8th Cir. 2010)).

For example, courts

have upheld against Eighth Amendment challenges such sentences as
a 107-year and 1-month sentence for a defendant's five § 924(c)
convictions, United States v. McDonel, 362 F. App'x 523, 530 (6th
Cir.), cert. denied, 562 U.S. 1061 (2010); a 132-year and 1-day
sentence, of which 125 years were for § 924(c) convictions, United
States v. Ezell, 265 F. App'x 70, 72 (3d. Cir. 2008); a 147-year
and 8-month sentence based, in large part, on a defendant's six
§ 924(c) convictions, United States v. Watkins, 509 F.3d 277, 282

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(6th Cir. 2007); and a 155-year sentence for seven § 924(c)
convictions, United States v. Hungerford, 465 F.3d 1113, 1117-18
(9th Cir. 2006), cert. denied, 550 U.S. 938 (2007). Rivera-Ruperto
has not presented any contrary authority upon which we might base
a departure from our sister circuits' holdings here.
At oral argument, counsel for Rivera-Ruperto argued that
we should be swayed by the fact that, in this case, the crime
involved fake drug deals.

A near two life-term punishment where

no real drugs and no real drug dealers were involved, he contended,
is a punishment that is grossly disproportionate on its face.

But

in coming to this sentence, the judge below was guided by and
correctly employed a sentencing scheme that is written into statute
-- a statute that makes no distinction between cases involving
real versus sham cocaine.

At each of the six stings, in fact,

Rivera-Ruperto repeatedly and voluntarily showed up armed and
provided security services for what he believed to be illegal
transactions between real cocaine dealers. The crime of possessing
a firearm in furtherance of such a drug trafficking offense is a
grave one, and Congress has made a legislative determination that
it requires harsh punishment.
we

see

no

Eighth

Given the weight of the case law,

Amendment

route

for

second-guessing

that

legislative judgment.
We
established

thus
that

cannot
his

conclude

sentence,

which

- 36 -

that
is

Rivera-Ruperto
largely

due

to

has
his

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consecutive sentences under § 924(c), is grossly disproportionate
to the crime, so as to trigger Eighth Amendment protections.21

21

Because Rivera-Ruperto fails to establish that his
sentence is grossly disproportionate, we need not reach the last
two criteria -- a comparison of his sentence with sentences
received by other offenders in the same jurisdiction or a
comparison of his sentence with sentences imposed for the same
crime in other jurisdictions.
Nevertheless, we note that in
comparing Rivera-Ruperto's sentence, the dissent relies largely on
the rationale of Judge Cassell in United States v. Angelos, 345 F.
Supp. 2d 1227 (D. Utah 2004), aff'd, 433 F.3d 738 (10th Cir. 2006).
However, despite Judge Cassell's misgivings about the resulting
sentence under § 924(c) for a 24 year old first-time offender in
that case, he ultimately (and we think correctly) ruled that:
The court's role in evaluating § 924(c) is quite limited.
The court can set aside the statute only if it is
irrational
punishment
without
any
conceivable
justification or is so excessive as to constitute cruel
and unusual punishment in violation of the Eighth
Amendment.
After careful deliberation, the court
reluctantly concludes that it has no choice but to impose
the 55 year sentence. While the sentence appears to be
cruel, unjust, and irrational, in our system of
separated powers Congress makes the final decisions as
to
appropriate
criminal
penalties.
Under
the
controlling case law, the court must find either that a
statute has no conceivable justification or is so
grossly disproportionate to the crime that no reasonable
argument can be made [on] its behalf. If the court is
to fairly apply these precedents in this case, it must
reject [the defendant's] constitutional challenges.
Angelos, 345 F. Supp. 2d at 1230.
Similarly, we cannot find that the sentence imposed pursuant
to § 924(c) has no conceivable justification or is so grossly
disproportionate that no reasonable argument can be made on its
behalf.
However unfair we may deem the life sentence here, we
cannot say that the Constitution forbids it.

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CONCLUSION
Our job now finished, we affirm for the reasons we have
stated above.

A second opinion, in which we address Rivera-

Ruperto's separate challenges as to his second trial, issues
herewith.

-Dissenting Opinions Follows-

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TORRUELLA, Circuit Judge (Dissenting).

Entry ID: 6062260

The majority

today affirms a sentence of 160 years and one month without the
possibility of parole for Rivera-Ruperto.

The transgression for

which Rivera-Ruperto was punished in such an extreme manner was
his participation as a security guard in several fake transactions,
while

the

FBI

duped

Rivera-Ruperto

composite was actually illegal drugs.

into

believing

that

the

The FBI ensured that more

than five kilograms of composite moved from one agent's hands to
another at each transaction; the FBI also made sure that the rigged
script included Rivera-Ruperto's possession of a pistol at each
transaction.

This combination -- more than five kilograms of

composite, a pistol, and separate transactions -- triggered the
mandatory consecutive minimums of 18 U.S.C. § 924(c), which make
up 130 years of Rivera-Ruperto's sentence.
In a real drug transaction, all participants would be
guilty of a crime.

And, in general, the greater their knowledge

of the crime would be, the harsher the law would punish them.

In

the fictitious transaction we are faced with today, however, only
the

duped

participants,

who

transpired, are punished.

had

no

knowledge

of

what

truly

The other participants are not only

excused, but indeed rewarded for a job well done.
If

Rivera-Ruperto

had

instead

knowingly

committed

several real rapes, second-degree murders, and/or kidnappings, he
would have received a much lower sentence; even if Rivera-Ruperto

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had taken a much more active role in, and brought a gun to, two
much larger real drug deals, he would still have received a much
lower sentence.22

For these and many other crimes Rivera-Ruperto

would have received sentences that would see him released from
prison during the natural term of his life.

For the fictitious

transgressions concocted by the authorities, however, RiveraRuperto will spend his entire life behind bars -- a sentence given
to first-degree murderers, 18 U.S.C. § 1111, or those who cause
death by wrecking a train carrying high-level nuclear waste.

18

U.S.C. § 1992.
From the majority's approval of the draconian sentence
imposed in this case,

I respectfully dissent.

Rivera-Ruperto's

sentence is grossly disproportionate to his offense, and therefore
violates the Eighth Amendment to the Constitution.
seemingly

excessively

harsh

sentences

have

While some

withstood

Eighth

Amendment challenges, such harsh sentences have been sanctioned
only in the context of recidivists or those who otherwise dedicated

22

See, e.g., United States v. Carlos Cruz, 352 F.3d 499,
509-10 (1st Cir. 2003) (affirming a sentence of 32 years given to
an actual drug dealer -- who was caught with actual cocaine,
heroin, cocaine base, two machine guns, a rifle, a pistol, and a
large amount of ammunition -- on seven counts related to possession
with intent to distribute illegal drugs and to possession of
firearms); United States v. Grace, case no. 1-16-cr-0039-001 (D.
Maine Dec. 13, 2016) (sentence of 15 years for conspiracy to
distribute and possess 100 or more grams of heroin. Defendant had
two prior convictions and admitted to importing more than 20,000
bags of cocaine).

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themselves to a life of crime -- a context that explained the
severity of the sentences.

But Rivera-Ruperto has no criminal

record, nor has he dedicated himself to a life of crime.

Not even

under the infamous § 924(c) has a first-time offender like RiveraRuperto ever been condemned to spend his entire life in jail.23
I.

The Eighth Amendment

The Court's cases addressing the proportionality of
sentences fall within two general classifications.
The first involves challenges to the length of termof-years sentences given all the circumstances in a
particular case. The second comprises cases in which
the Court implements the proportionality standard by
certain categorical restrictions on the death
penalty.
In the first classification the Court considers all
of the circumstances of the case to determine whether
the sentence is unconstitutionally excessive.
Graham v. Florida, 560 U.S. 48, 59 (2010).
The second classification has evolved to encompass not
only the death penalty, but also prison sentences.

See id. at 61-

62, 82 (holding that a sentence of life without the possibility of
parole for non-homicide offenses by juveniles violates the Eighth

23

See infra Section II.A. Although § 924(c) has rightly
been the subject of much scathing criticism, the statute as such
is not the focus of this dissent. See, e.g., Judge Paul Cassell,
Statement on Behalf of the Judicial Conference of United States
from U.S. District Judge Paul Cassell before the House Judiciary
Committee Subcommittee on Crime, Terrorism, and Homeland Security,
2007 WL 3133929, Fed. Sent'g Rep. 19(5) (2007). Rather, what is
at issue today is the proportionality of Rivera-Ruperto's
sentence, not the proportionality of sentences under § 924(c) in
general.

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Amendment);

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Miller v. Alabama, 132 S. Ct. 2455, 2469 (2012)

(holding that a mandatory sentence of life without parole for
juvenile offenders violates the Eighth Amendment).
In the present case, this court is faced with a challenge
that falls under the first classification: a challenge to the
length of Rivera-Ruperto's sentence based on the circumstances of
his case; in other words, an as-applied constitutional challenge
to the length of Rivera-Ruperto's sentence.
The

Supreme

Court's

jurisprudence

in

this

first

classification is animated by the principle of proportionality in
punishment, as well as by deference to the legislature's judgment
as to what punishment is merited.
A.

Proportionality
The principle of proportionality is deeply embedded into

the very roots of our legal system.
284 (1983).

Solem v. Helm, 463 U.S. 277,

"In 1215 three chapters of Magna Carta were devoted

to the rule that 'amercements' [the most common criminal sanction
at

the

time]

may

not

be

excessive"

--

and

disproportionate

penalties were invalidated accordingly by the royal courts.

Id.

at 284-85. When the Framers adopted the language of the Eighth
Amendment from the English Bill of Rights -- which provided that
"excessive Baile ought not to be required nor excessive Fines
imposed nor cruell and unusuall Punishments inflicted" -- they
also adopted the principle of proportionality, for it was a major

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theme of the era that Americans had all the rights of English
subjects.

Id. at 285-86.
The

principle

of

proportionality

historical interest, however.
on

to

observe

that

is

not

merely

of

In that same case, the Court went

"[t]he

constitutional

principle

of

proportionality has been recognized explicitly in this Court for
almost a century."

Id. at 286.

The Court proceeded to cite from

no fewer than eleven of its precedents ranging from 1892 to 1982,
in which the principle of proportionality was recognized24 -- and

24

To wit: O’Neil v. Vermont, 144 U.S. 323, 339-40 (1892)
(Field, J., dissenting) (the Eighth Amendment "is directed ...
against all punishments which by their excessive length or severity
are greatly disproportioned to the offenses charged"); Trop v.
Dulles, 356 U.S. 86, 100 (1958) (plurality opinion); id. at 111
(Brennan, J., concurring); id. at 125–26 (Frankfurter, J.,
dissenting). Weems v. United States, 217 U.S. 349, 367, 372-73
(1910) ("that it is a precept of justice that punishment for crime
should be graduated and proportioned to offense," and endorsing
the principle of proportionality as a constitutional standard);
Robinson v. California, 370 U.S. 660, 667 (1962) ("But the question
[of excessive punishment under the Eighth Amendment] cannot be
considered in the abstract. Even one day in prison would be a cruel
and unusual punishment for the 'crime' of having a common cold.");
Enmund v. Florida, 458 U.S. 782 (1982) (death penalty excessive
for felony murder when defendant did not take life, attempt to
take life, or intend that a life be taken or that lethal force be
used); Coker v. Georgia, 433 U.S. 584, 592 (1977) (plurality
opinion) ("sentence of death is grossly disproportionate and
excessive punishment for the crime of rape"); id., at 601, (Powell,
J., concurring in the judgment in part and dissenting in part)
("ordinarily death is disproportionate punishment for the crime of
raping an adult woman"); Hutto v. Finney, 437 U.S. 678, 685 (1978);
Ingraham v. Wright, 430 U.S. 651, 667 (1977); Gregg v. Georgia,
428 U.S. 153, 171–72 (1976) (opinion of Stewart, Powell, and
Stevens, JJ.); Hutto v. Davis, 454 U.S. 370, 374, and n.3 (1982)
(per curiam) (recognizing that some prison sentences may be
constitutionally disproportionate); Rummel v. Estelle, 445 U.S.
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this was not even an exhaustive list.
12.

Entry ID: 6062260

See id. at 287-88, n.11,

The Court proceeded to hold that a punishment of life without

the possibility of parole was disproportionate to the offense of
issuing a no account check in the amount of $100 (even though it
was the defendant's seventh offense) -- and that this sentence
therefore violated the Eighth Amendment.

Id. at 303.

The Supreme Court has continued to recognize that prison
sentences must be proportional under the Eighth Amendment in every
case that has dealt with that question since Solem.25

See Harmelin

v. Michigan, 501 U.S. 957, 997 (1991) (Kennedy, J., concurring)26
("[t]he Eighth Amendment proportionality principle also applies to
noncapital sentences"); Ewing v. California, 538 U.S. 11, 20 (2003)
("The Eighth Amendment . . . contains a 'narrow proportionality
principle' that 'applies to noncapital sentences.'") (internal
citations omitted); id. at 33 (Stevens, Souter, Ginsburg, Breyer,
JJ., dissenting) ("The concurrences prompt this separate writing
to emphasize that proportionality review is not only capable of

263, 272, n.11 (1980) ("[o]utside the context of capital
punishment, successful challenges to the proportionality of
particular sentences [will be] exceedingly rare").
25

I here limit my consideration to non-capital cases, because
capital cases fall within the second classification of Eighth
Amendment proportionality challenges. Note, however, that in
capital cases, the principle of proportionality certainly applies
as well. See, e.g., Graham, 560 U.S. at 59-61.
26

This
concurrence
has
since
"controlling." Graham, 560 U.S. at 59.

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been

described

as

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judicial application but also required by the Eighth Amendment.");
Lockyer v. Andrade, 538 U.S. 63, 72 (2003) ("Through this thicket
of Eighth Amendment jurisprudence, one governing legal principle
emerges as 'clearly established' under § 2254(d)(1): A gross
disproportionality principle is applicable to sentences for terms
of

years.");

Graham,

560

U.S.

at

59

("The

concept

of

proportionality is central to the Eighth Amendment."); Miller, 132
S. Ct. at 2463 (same).27
B.

Deference to the Legislature
The same case law is also clear that respect for the

judgment of the legislature as to what constitutes appropriate
punishment is in order.

See, e.g., Solem, 463 U.S. at 290 ("[w]e

hold as a matter of principle that a criminal sentence must be
proportionate to the crime for which the defendant has been
convicted. Reviewing courts, of course, should grant substantial
deference to the broad authority that legislatures necessarily
possess in determining the types and limits of punishments for
crimes"); Ewing, 538 U.S. at 24 (noting that "[t]hough three
strikes laws may be relatively new, our tradition of deferring to
state

legislatures

in

making

and

27

implementing

such

important

Although the position that the Eighth Amendment does not
contain a proportionality principle was occasionally raised, it
never achieved a majority in the Supreme Court, and has been
squarely rejected. See, e.g., Miller, 132 S. Ct. at 2483 ("The
[Eighth Amendment] does not contain a proportionality principle.")
(Thomas, Scalia, JJ., dissenting) (internal citation omitted).

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policy decisions is longstanding", and adding "[o]ur traditional
deference to legislative policy choices finds a corollary in the
principle that the Constitution 'does not mandate adoption of any
one

penological

therefore

theory'").

sometimes

The

described

proportionality
as

"narrow,"

principle
and

only

is
in

"exceedingly rare" instances of "gross disproportionality" should
the courts apply the Eighth Amendment to overturn a sentence. See,
e.g., id. at 20, 21.
C.

The Three-Step Analysis
Thus it is clear that proportionality is of crucial

importance in our sentencing law, but its "precise contours . . .
are unclear".
these

contours

Lockyer, 538 U.S. at 72, 73.
are

primarily

determined

It is also clear that
by

deference

legislature's judgment as to appropriate punishment.

to

the

This has led

to the emergence of a three-step analysis that assesses both
proportionality and the legislature's judgment.

In performing

this three-part test, courts must look at the actual severity of
a defendant's offenses (as opposed to merely looking at the laws
he violated), as well as look at the actual severity of the penalty
(rather than merely at the name of the penalty); and courts must
give recidivism great weight when assessing the gravity of an
offense, and thus when justifying a harsh sentence.

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The Three Steps
The controlling opinion in Harmelin explained its
approach for determining whether a sentence for a term
of years is grossly disproportionate for a particular
defendant's crime. A court must begin by comparing
the gravity of the offense and the severity of the
sentence.
'[I]n the rare case in which [this]
threshold comparison . . . leads to an inference of
gross disproportionality' the court should then
compare the defendant's sentence with the sentences
received by other offenders in the same jurisdiction
and with the sentences imposed for the same crime in
other jurisdictions.
If this comparative analysis
'validate[s] an initial judgment that [the] sentence
is grossly disproportionate,' the sentence is cruel
and unusual.

Graham, 560 U.S. at 60 (internal citations omitted; alterations in
original).
2.

Actual Severity of the Offense and of the Punishment
In performing the three-step analysis, the Supreme Court

has considered the actual severity of the acts committed by
defendants, as well as the importance of the laws they violated.
See, e.g., Ewing, 538 U.S. at 18-19, 28 (detailing defendant's
past nine criminal convictions and considering the dollar value of
the merchandise stolen by the defendant in his latest conviction).
Similarly, the Supreme Court has been clear that for the
purposes of the three-step analysis, courts must look to the actual
severity of the penalty -- that is, the actual amount of time a
defendant will serve in prison -- and not to what his penalty is
called.

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[The
defendant's]
present
sentence
is
life
imprisonment without possibility of parole. . . .
Helm will spend the rest of his life in the state
penitentiary. This sentence is far more severe than
the life sentence we considered in Rummel v. Estelle.
Rummel was likely to have been eligible for parole
within 12 years of his initial confinement, a fact on
which the Court relied heavily.
Solem, 463 U.S. at 297.28
The Supreme Court reaffirmed this approach in 2012, its
most recent pronouncement on the issue:
The two 14–year–old offenders in these cases were
convicted of murder and sentenced to life imprisonment
without the possibility of parole. . . . State law
mandated that each juvenile die in prison even if a
judge or jury would have thought that his youth and
its attendant characteristics, along with the nature
of his crime, made a lesser sentence (for example,
life with the possibility of parole) more appropriate.
Miller, 132 S. Ct. at 2460 (original emphasis).
3.

Recidivism
The Supreme Court has upheld several harsh sentences for

seemingly relatively minor crimes.

The Supreme Court reasoned

that the severity of these sentences was justified because they
involved recidivist offenders and recidivism was a legitimate

28

The Court explicitly rejected the Government's argument
that the possibility of executive clemency made a sentence of life
without the possibility of parole the same as a sentence of life
with the possibility of parole. Id. at 303 ("The possibility of
commutation is nothing more than a hope for 'an ad hoc exercise of
clemency.' It is little different from the possibility of executive
clemency that exists in every case in which a defendant challenges
his sentence under the Eighth Amendment. Recognition of such a
bare possibility would make judicial review under the Eighth
Amendment meaningless.").

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basis on which a legislature could elect to sentence more harshly.
For instance, in Rummel v. Estelle, the Supreme Court upheld a
sentence of life with the possibility of parole for obtaining
$120.75 under false pretenses, but reasoned that:
Moreover, given Rummel's record, Texas was not
required to treat him in the same manner as it might
treat him were this his first "petty property
offense." Having twice imprisoned him for felonies,
Texas was entitled to place upon Rummel the onus of
one who is simply unable to bring his conduct within
the social norms prescribed by the criminal law of
the State.
The purpose of a recidivist statute such as that
involved here is not to simplify the task of
prosecutors, judges, or juries. Its primary goals are
to deter repeat offenders and, at some point in the
life of one who repeatedly commits criminal offenses
serious enough to be punished as felonies, to
segregate that person from the rest of society for an
extended period of time. This segregation and its
duration are based not merely on that person's most
recent offense but also on the propensities he has
demonstrated over a period of time during which he
has been convicted of and sentenced for other crimes.
Rummel, 445 U.S. at 284.
In Ewing, to use another example, the Supreme Court
devoted an entire section of its opinion to explaining that the
defendant's sentence of 25 years to life for stealing three golf
clubs under California's three strikes law must be understood in
the

context

of

recidivism,

and

explained:

"California's

justification is no pretext. Recidivism is a serious public safety
concern in California and throughout the Nation."
at 26.

Ewing, 538 U.S.

"In weighing the gravity of Ewing's offense, we must place

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on the scales not only his current felony, but also his long
history of felony recidivism."
Indeed,

of

the

Id. at 29.

seven

cases

that

address

as-applied

proportionality challenges under the Eighth Amendment, five deal
with recidivist offenders.29
(Harmelin)

deals

with

a

Of the remaining two cases, one

career

criminal

(another

important

justification for meting out sentences that appear harsh on their
face); and in the final case (Weems) the punishment was held to
violate the Eighth Amendment.
II.
A.

Discussion

Three-Step Test
Rivera-Ruperto's case has no difficulty clearing the

first step of the three-step analysis, in which "[a] court must
begin by comparing the gravity of the offense and the severity of
the sentence.

'[I]n the rare case in which [this] threshold

comparison . . . leads to an inference of gross disproportionality'
the

court

analysis]."

should

then

[proceed

to

the

second

step

of

the

Graham, 560 U.S. at 59 (internal citations omitted).

In over forty years on the federal bench, I have never seen so
disproportionate a penalty handed down, particularly where the
offense is based on fiction.
this

sentence

29

to

be

vastly

I am certainly not alone in finding
disproportionate

to

the

To wit, Rummel, Hutto, Solem, Ewing, Lockyer.

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Speaking on behalf of the Judicial Conference of the United States,
Judge Paul Cassell, after describing mandatory minimum sentences
--

in

particular

under

§

924(c)

--

as

"one-size-fits-all

injustice," "bizarre," "irrational," "cruel and unusual, unwise
and

unjust,"

concluded

that

the

mandatory

minimum

system

of

sentencing "must be abandoned in favor of a system based on
principles of fairness and proportionality."30
Commission,

too,

views

sentences

such

as

The Sentencing

Rivera-Ruperto's

as

disproportionate -- not only would its Guidelines recommend a far
lower sentence, but the Commission stated that sentences as a
result of § 924(c) stacking "can lead to sentences that are
excessively
committed."31

severe

and

disproportionate

to

the

offense

As an example, the Commission cited the case of

Weldon Angelos, a marijuana dealer who received a sentence of 61.5
years (55 years of which was mandatory minimum sentence under

30

Judge Paul Cassell, Statement on Behalf of the Judicial
Conference of United States from U.S. District Judge Paul Cassell
before the House Judiciary Committee Subcommittee on Crime,
Terrorism, and Homeland Security, 2007 WL 3133929, Fed. Sent'g
Rep. 19(5) (2007) (quoting Senior Judge Vincent L. Broderick,
Southern District of New York, speaking for the Criminal Law
CommRRep. 19(5) (2007) (quoting Senior Judge Vincent L. Broderick,
Southern District of New York, speaking for the Criminal Law
Committee of the Judicial Conference in testimony before the
Subcommittee on Crime and Criminal Justice of the House Committee
on the Judiciary, July 28, 1993).
31

United States Sentencing Commission, 2011 Report to the
Congress: Mandatory Minimum Penalties in the Federal Criminal
Justice System 359 (2011).

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§ 924(c) for bringing (but not using or brandishing) a gun to three
marijuana deals)32 -- Rivera-Ruperto, however, is faced with a
sentence of 160 years (130 years due to stacking under § 924(c)).
Rivera-Ruperto's case also has no trouble passing the
second step, namely a comparison of "the defendant's sentence with
the

sentences

jurisdiction."

received

by

other

offenders

Graham, 560 U.S. at 60.

in

the

same

"If more serious crimes

are subject to the same penalty, or to less serious penalties,
that is some indication that the punishment at issue may be
excessive."

Solem, 463 U.S. at 291.

Rivera-Ruperto received,

effectively, a mandatory sentence of life without the possibility
of

parole

lifetimes.

("LWOP")

--

because

160

years

is

about

two

human

The district court has effectively condemned him to

die in prison.

As noted above, this court is to consider the

actual time a defendant is to spend incarcerated -- in RiveraRuperto's case, that means his whole life.
I.C.2.

See supra Section

If, however, one compares his offense to other offenses

that would result in mandatory LWOP under federal law, then his
offense pales in comparison.
nine

statutes

32

that

I have been able to locate forty-

prescribe

a

mandatory

penalty

of

LWOP.33

Id. n.903.

33

See United States Sentencing Commission, Mandatory Minimum
Penalties in the Federal Criminal Justice System, App. A (2011).

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Seventeen of these are for first degree murder.34

Entry ID: 6062260

The general

statute imposing a mandatory minimum for first degree murder, 18
U.S.C. § 1111, goes back to 1790.

Congress has steadily widened

its application since then, and it now covers many specific
situations, from killing the president, 18 U.S.C. § 1751(a), to
killing an eggs product quality inspector, 21 U.S.C. § 1041(b).
Other statutes mandate a sentence of LWOP for such crimes as
genocide killing -- perhaps the gravest crime imaginable -- 18
U.S.C. § 1091, wrecking a train carrying high level nuclear
material and thereby causing death, 18 U.S.C. § 1992, and hostage
taking resulting in death, 18 U.S.C. § 1203.

Rivera-Ruperto's

offenses simply do not rise to the level of the offenses in this
chart.

The complete chart follows.

Statute (Guideline)
1

Description

15 U.S.C. § 1825(a)(2)(c)
(§2A1.1)

First degree murder of horse
official

Date
Enacted35
1970

Minimum
Term36
Life**

34

Note that the statutes permit the death penalty for first
degree murder.
18 U.S.C. § 1111.
Because the statutes only
mandate a sentence of LWOP and the death penalty is given only
rarely, I include the statutes in the comparison. After all, the
statutes reflect Congress's judgment that first degree murder,
without more -- already a heinous offense far worse that RiveraRuperto's -- is adequately punished by LWOP.
35

I follow the Sentencing Commission here by indicating the
year during which the mandatory minimum was first enacted with
respect to the substantive offense proscribed by the relevant
statute.
See supra n.11, Mandatory Minimum Penalties in the
Federal Criminal Justice System.
36

All sentences are without the possibility of parole, for
parole has been abolished in the federal system. See Pub. L. No.
98-473, 98 Stat. 1987 (codified as amended in scattered sections
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Statute (Guideline)

Description

2

18 U.S.C. § 115 (§§2A1.1,
2A1.2, 2A2.1, 2X1.1)

3

18 U.S.C.
(§2M6.1)

4

18 U.S.C. § 229a

5

18 U.S.C. § 351 (§§2A1.1,
2A1.2, 2A1.3, 2A1.4)

6

18
U.S.C.
§ 924(c)(1)(C)(ii)(§2K2.
4)

7

18
U.S.C.
(§2K2.5)

8
9

18 U.S.C. § 1091 (§2H1.3)
18
U.S.C.
§
1111
(§§2A1.1, 2A1.2)
18
U.S.C.
§
1114
(§§2A1.1, 2A1.2, 2A1.3,
2A1.4, 2A1.2)
18
U.S.C.
§
1116
(§§2A1.1, 2A1.2, 2A1.3,
2A1.4, 2A2.1)

First
degree
murder
of
federal
official's
family
member
If the death of another
results
from
a
person's
violation of subsection (a)
(knowingly produce, engineer,
synthesize, acquire, transfer
directly
or
indirectly,
receive,
possess,
import,
export, or use, or possess and
threaten
to
use,
variola
virus)
Develop/produce/acquires/tra
nsfer/possess/use
any
chemical weapon that results
in the death of another
person.
First
degree
murder
of
Congress, Cabinet, or Supreme
Court member
Second
or
subsequent
conviction
of
using
or
carrying a firearm during a
crime of violence or drug
trafficking crime and fire
arm is a machine gun or
destructive device or the
firearm is equipped with a
silencer or muffler
First degree murder involving
the possession or use of a
firearm or other dangerous
weapon in a Federal Facility
Genocide killing
First degree murder

10

11

§

175c(c)(3)

§

930(c)

12

18
U.S.C.
§
(§§2A1.1, 2A1.2)

1118

13

18
U.S.C.
§
1119(b)
(§§2A1.1, 2A1.2, 2A1.3,
2A1.4, 2A2.1)

Entry ID: 6062260

Date
Enacted35
1984

Minimum
Term36
Life**

2004

Life

1998

Life**

1971

Life**

1986

Life

1988

Life**

1988
1790

Life**
Life**

of

1934

Life**

First
degree
murder
of
foreign officials, official
guests, or internationally
protected persons
Murder
in
a
federal
correctional
facility
by
inmate sentenced to a term of
life imprisonment
First degree murder of a U.S.
national by a U.S. national

1972

Life**

1994

Life**

1994

Life**

First
degree
murder
federal officers

of 18 U.S.C. and 28 U.S.C.).

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Statute (Guideline)

14

15

16
17
18
19

18
U.S.C.
§
1120
(§§2A1.1, 2A1.2, 2A1.3,
2A1.4)
18 U.S.C. § 1121(a)(1)
(§§2A1.1, 2A1.2)

18 U.S.C. § 1201(a)
18
U.S.C.
§
1203
(§§2A4.1, 2X1.1)
18 U.S.C. § 1503(b)(1)
(§2J1.2)
18 U.S.C. § 1512(a)(1)
(§§2A1.1, 2A1.2, 2A1.3,
2A2.1)

20

18 U.S.C. § 1512(a)(2)
(§§ 2A1.1, 2A1.2, 2A1.3,
2A2.1)

21

22

18 U.S.C. § 1512(a)(3)(A)
(§§2A1.1, 2A1.2, 2A1.3,
2A2.1)
18 U.S.C. § 1651

23
24

18 U.S.C. § 1652
18 U.S.C. § 1653

25

18 U.S.C. § 1655

26
27

18 U.S.C. § 1661
18
U.S.C.
§
1751(a)
(§§2A1.1, 2A1.2, 2A1.3,
2A1.4)

28

18
U.S.C.
(§2E1.4)

29

18 U.S.C. § 1992

30

18
U.S.C.
§
2113(e)
(§§2A1.1, 2B3.1)

§

1958(a)

Page: 55

Date Filed: 01/13/2017

Description
while
outside
the
United
States
Murder by escaped federal
prisoner
First degree murder of a state
or
local
law
enforcement
officer
or
any
person
assisting in a federal crime
investigation
Kidnapping
Hostage taking resulting in
the death of any person
First degree murder of an
officer of the court or juror
First degree murder of any
person with the intent to
prevent their attendance or
testimony
in
an
official
proceeding
Obstructing justice by using,
or
attempting
to
use,
physical
force
against
another
Obstructing
justice
by
tampering with a witness,
victim, or an informant
Piracy under the laws of the
nation
Piracy by U.S. citizen
Piracy against the United
States by an alien
Piracy in the form of assault
on a commander
Robbery ashore by a pirate
Killing the President of the
United States, the next in
order of succession to the
Office of the President, or
any person who is acting as
the President of the United
States;
or
any
person
employed in the Executive
Office of the President or
Office of the Vice President
Causing death through the use
of
interstate
commerce
facilities in the commission
of a murder-for-hire
Wrecking train carrying high
level
nuclear
waste
and
thereby causing death
Causing death in the course
of a bank robbery, avoiding

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Entry ID: 6062260

Date
Enacted35

Minimum
Term36

1996

Life**

1996

Life**

2003
2003

Life**
Life**

1948

Life**

1982

Life**

1982

Life

1982

Life

1790

Life

1790
1790

Life
Life

1790

Life

1790
1965

Life
Life**

1984

Life**

2006

Life**

1934

Life**

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Document: 00117105554

Statute (Guideline)

§

18
U.S.C.
(§2A3.1)

2241(c)

32

18
U.S.C.
(§2K2.1)

33

18 U.S.C. § 2332(h)(c)(3)
(§2M6.1)

34

18 U.S.C. § 3559(c)(1)

35

18 U.S.C. § 3559(d)(1)

36

18 U.S.C. § 3559(e)(1)

§

Date Filed: 01/13/2017

Description

31

§

Page: 56

2332g

37

21
U.S.C.
(§2N2.1)

461(c)

38

21 U.S.C. § 675 (§§2A1.1,
2A1.2,
2A1.3,
2A1.4,
2A1.2, 2A2.3)

39

21 U.S.C. § 841(b)(1)(A)
(§2D1.1)

apprehension
for
a
bank
robbery, or escaping custody
after a bank robbery
Second or subsequent offense,
engaging in a sexual act with
a child under the age of 12,
or engaging in a sexual act
by force with a child who is
above the age of 12, but under
the age of 16
If death of another results
from knowingly produc[ing],
acquir[ing], transferr[ing],
or
possess[ing]
missile
systems designed to destroy
aircraft
If
death
results
from
knowingly
produc[ing],
acquir[ing], transferr[ing],
or possess[ing] any weapon
designed to release radiation
or radioactivity at a level
dangerous to human life
Upon conviction for a serious
violent felony, if offender
has two or more prior serious
violent felony convictions,
or one or more prior serious
violent felony convictions
and one or more prior serious
drug offense conviction
If the death of a child less
than 14 years results from a
serious violent felony
Where a federal sex offense
committed against a minor and
the offender has a prior sex
conviction in which minor was
a victim.
Killing any person engaged in
or on account of performance
of his official duties as
poultry or poultry products
inspector.
Killing any person engaged in
or on account of performance
of his official duties as a
meat inspector
Second offense manufacturing,
distributing, or possessing a
controlled
substance
or
counterfeit substance with
intent to distribute,
if
death
or
serious
bodily

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Entry ID: 6062260

Date
Enacted35

Minimum
Term36

1986

Life**

2004

Life

2004

Life

2003

Life†,††

2003

Life

2003

Life**,
†

1957

Life**

1907

Life**

1986

Life*,†

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Statute (Guideline)

Page: 57

Date Filed: 01/13/2017

Description

Entry ID: 6062260

Date
Enacted35

Minimum
Term36

1986

Life*,†

1984

Life*,†

injury results from the use
of such substance

40

41

21 U.S.C. § 841(b)(1)(A)
(§2D1.1)

21 U.S.C. § 841(b)(1)(B)
(§2D1.1)

21
U.S.C.
§§
859(b)
(distribution to a person
under the age of 21), 860(b)
(distribution or manufacture
in or near a school or
college),
and
861(c)
(employing or using a person
under the age of 21 to engage
in a controlled substance
offense) all incorporate the
minimum terms set by
§ 841(b)(1)(A).
Third offense, manufacturing,
distributing, or possessing a
controlled
substance
or
counterfeit substance with
intent to distribute
21
U.S.C.
§§
859(b)
(distribution to a person
under the age of 21), 860(b)
(distribution or manufacture
in or near a school or
college),
and
861(c)
(employing or using a person
under the age of 21 to engage
in a controlled substance
offense) all incorporate the
minimum terms set by
§ 841(b)(1)(A).
Second
or
any
subsequent
offense,
manufacturing,
distributing or possessing a
controlled
substance
or
counterfeit substance with
intent to distribute, death
or
serious
bodily
injury
results
21
U.S.C.
§§
859(b)
(distribution to a person
under the age of 21), 860(b)
(distribution or manufacture
in or near a school or
college),
and
861(c)
(employing or using a person
under the age of 21 to engage
in a controlled substance
offense) all incorporate the
minimum terms set by
§ 841(b)(1)(A).

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Statute (Guideline)
42

21
U.S.C.
(§2D1.5)

§

Page: 58

Description

848(b)

Date Filed: 01/13/2017

Entry ID: 6062260

Date
Enacted35
1986

Minimum
Term36
Life**

Any
offense;
principal,
administrator, organizer, or
leader
("kingpin")
of
continuing
criminal
enterprise
Life*,†
43 21 U.S.C. § 960(b)(1) Second
or
any
subsequent 1986
offense, unlawful import or
(§2D1.5)
export
of
controlled
substance, death or serious
bodily injury results
Life†
44 21 U.S.C. § 960(b)(2)
Second
or
any
subsequent 1986
offense, unlawful import or
export
of
controlled
substance, death or serious
bodily injury results
Life†
45 21 U.S.C. § 960(b)(3)
Second
or
any
subsequent 1986
offense, unlawful import or
export
of
controlled
substance, death or serious
bodily injury results
Life**
46 21 U.S.C. § 1041(b)
Killing any person engaged in 1970
or on account of performance
of his official duties under
Chapter
15-Eggs
Product
Inspection
Life
47 42
U.S.C.
§
2272(b) Violation
of
prohibitions 1954
(§2M6.1)
governing
atomic
weapons;
death of another resulting
Life**
48 49
U.S.C. Committing or attempting to 1958
§ 46502(a)(2)(B)
commit aircraft piracy in
(§§2A5.1, 2X1.1)
special aircraft jurisdiction
of the U.S.; resulting in
death of another individual
Life**
49 49
U.S.C. Violation of Convention for 1958
§ 46502(b)(1)(B)
the Suppression of Unlawful
(§§2A5.1, 2X1.1)
Seizure of Aircraft outside
special aircraft jurisdiction
of U.S.; resulting in death
of another individual
* Safety valve applies (18 U.S.C. § 3553(f)), allowing for sentencing below the
mandatory minimums for certain low-level, first-time offenders.
** Statute also permits the imposition of the death penalty.
† Recidivism required for the mandatory term of life imprisonment to apply.
††
18 U.S.C. § 3582(c)(1), commonly known as the "compassionate release"
provision, applies. This provision allows certain criminals to be released at
age 70 if they have served at least 30 years in prison.

If one approaches the analysis under this second step
from another angle, one arrives at the same conclusion.

That is,

if one looks to offenses far graver than those Rivera-Ruperto

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committed, one finds that they carry far less severe sentences
than Rivera-Ruperto's.

In sentencing to a mandatory term of 55

years a defendant who had committed three offenses under § 924(c),
Judge Cassell compiled a table of offenses under federal law that
would result in a shorter sentence than those 55 years -- but were
clearly graver than the defendant's offenses.

Judge Cassell's

comparison applies even to Rivera-Ruperto's considerably longer
sentence.

Examples from his table include "an aircraft hijacker

(293 months), a terrorist who detonates a bomb in a public place
(235 months), a racist who attacks a minority with the intent to
kill and inflicts permanent or life-threatening injuries (210
months), a second-degree murderer, or a rapist."

United States v.

Angelos, 345 F. Supp. 2d 1227, 1244-45 (D. Utah 2004), aff'd, 433
F.3d 738 (10th Cir. 2006).

Judge Cassell went on to compare the

sentence before him to triple offenders, and arrived at the
conclusion that,
[a]mazingly,
[the
Defendant's]
sentence
under
§ 924(c) is still far more severe than criminals who
committed, for example, three aircraft hijackings,
three second-degree murders, three kidnappings, or
three rapes. . . . [Defendant] will receive a longer
sentence than any three-time criminal, with the sole
exception of a marijuana dealer who shoots three
people. ([The defendant] still receives a longer
sentence than a marijuana dealer who shoots two
people.)
Id. at 1246.

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Similarly telling is a comparison to the federal threestrikes provision, 18 U.S.C. § 3559(c).

This statute mandates

that a court impose a sentence of LWOP on a criminal with two prior
serious violent felony convictions when this criminal commits a
third such offense -- but such an offender can then be released at
age 70 if he has served at least 30 years in prison under 18 U.S.C.
§ 3582(c)(1), the so-called "compassionate release clause."

That

is,

been

if

Rivera-Ruperto

had

committed

a

violent

felony,

convicted, then committed a second violent felony, then been
convicted again, and then committed a third violent felony, and
been

convicted

yet

again,

he

--

even

though

a

seemingly

incorrigible recidivist -- would have been eligible for release at
age 70.

As a first-time offender sentenced under § 924(c),

however, Rivera-Ruperto will never be eligible for release.37

37

See also Angelos, 345 F. Supp. 2d at 1250-51 ("The
irrationality only increases when section § 924(c) is compared to
the federal 'three strikes' provision. Criminals with two prior
violent felony convictions who commit a third such offense are
subject to 'mandatory' life imprisonment under 18 U.S.C. § 3559(c)-the federal 'three–strikes' law. But then under 18 U.S.C. §
3582(c)(1)--commonly
known
as
the
'compassionate
release'
provision--these criminals can be released at age 70 if they have
served 30 years in prison. But because this compassionate release
provision applies to sentences imposed under § 3559(c)--not §
924(c)--offenders like [the Defendant] are not eligible. Thus,
while the 24–year–old [Defendant] must serve time until he is well
into his 70's, a 40–year–old recidivist criminal who commits second
degree murder, hijacks an aircraft, or rapes a child is potentially
eligible for release at age 70. In other words, mandatory life
imprisonment under the federal three-strikes law for persons
guilty of three violent felony convictions is less mandatory than
mandatory time imposed on the first-time offender under § 924(c).
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At the third, and final, step of the analysis, "the court
should . . .

compare [Rivera-Ruperto's sentence] . . . with the

sentences imposed for the same crime in other jurisdictions.

If

this comparative analysis 'validate[s] an initial judgment that
[the] sentence is grossly disproportionate,' the sentence is cruel
and unusual." Graham, 560 U.S. at 60 (internal citations omitted).
Rivera-Ruperto's
difficulty.

case

also

clears

this

final

step

without

Sentences for offenses like Rivera-Ruperto's are much

lower under state law.38

(This brings with it a number of serious

Again, the rationality of this arrangement is dubious.
This possibility, too, is no mere hypothetical. This
morning, the court had before it for sentencing Thomas Ray Gurule.
Mr. Gurule is 54–years–old with a lifelong history of criminal
activity and drug abuse. He has spent more of his life incarcerated
than he has in the community. He has sixteen adult criminal
convictions on his record, including two robbery convictions
involving dangerous weapons. His most recent conviction was for
carjacking. In August 2003, after failing to pay for gas at a
service station, Mr. Gurule was pursued by the station manager. To
escape, Mr. Gurule broke into the home of a young woman, held her
at knife point, stole her jewelry, and forced her to drive him
away from the scene of his crimes. During the drive, Mr. Gurule
threatened both the woman and her family.
For this serious offense--the latest in a long string of
crimes for which he has been convicted--the court must apparently
sentence Mr. Gurule to "life" in prison under 18 U.S.C. § 3559(c).
But because of the compassionate release provision, Mr. Gurule is
eligible for release after serving 30–years of his sentence. Why
Mr. Gurule, a career criminal, should be eligible for this
compassionate release while [the Defendant is not] is not obvious
to the court.").
38

Erik Luna and Paul Cassell, Mandatory Minimalism, 32
Cardozo L. Rev. 1, 16 (2010) ("Most drug and weapons crimes
amenable to federal mandatory minimums are actually prosecuted in
state courts pursuant to state laws carrying much lower
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issues, such as prosecutors choosing to bring cases in federal
court merely because of the higher sentences -- but such issues
are

not

the

focus

of

dissent.).39

this

There

is

also

some

suggestion that courts may need to look to foreign law in this
step of the analysis. In cases involving the second classification
of

Eighth

Amendment

challenges

--

applying

categorical

restrictions on the death penalty or LWOP -- the Supreme Court
"has looked beyond our Nation's borders for support for its
independent conclusion that a particular punishment is cruel and
unusual. . . . Today we continue that longstanding practice in
noting the global consensus against the sentencing practice in
question."

Graham, 560 U.S. at 80.

It is unclear whether in the

first classification of Eighth Amendment challenges -- such as the
as-applied challenge before us today -- courts should also look to

sentences.") (emphasis added).
39

Id. ("It is hardly disputed, however, that the possibility
of severe punishment can influence the choice of whether to pursue
a federal or state prosecution. For some, this prospect raises
serious questions about the propriety of bringing charges in
federal rather than state court, particularly where the
prosecution is pursued, not because the case implicates a special
national interest, but because it jacks up the potential
punishment."). See also Angelos, 345 F. Supp. 2d at 1243 ("Indeed,
the government conceded that [the Defendant's] federal sentence
[of 55 years in prison] after application of the § 924(c) counts
is more than he would have received in any of the fifty states.");
Id. at 1259 ("[Defendant's] sentence [of 55 years under § 924(c)]
is longer than he would receive in any of the fifty states. The
government commendably concedes this point in its brief, pointing
out that in Washington State [the Defendant] would serve about
nine years and in Utah would serve about five to seven years.").

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foreign law.
the

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Entry ID: 6062260

I therefore note that foreign law further supports

proposition

that

Rivera-Ruperto's

sentence

is

out

of

proportion to his crime, for "LWOP . . . scarcely exists elsewhere
in the world. Yet today, the number of defendants sentenced to
LWOP by American courts approaches 50,000. . . .

In fact, what

separates the American criminal justice system from the rest of
the world, and brands it as distinctively harsh, is the number of
inmates dispatched to prison for the duration of their lives,
without

offering

Germany,

France,

a

legal
and

mechanism

Italy

have

for

freedom."40

declared

LWOP

Indeed,
to

be

unconstitutional, and other European countries apply it only very
rarely.41

40

Craig S. Lerner, Who's Really Sentenced to Life Without
Parole?:
Searching for "Ugly Disproportionalities" in the
American Criminal Justice System, 2015 Wis. L. Rev. 789, 792
(2015). See Ashley Nellis, Throwing Away the Key: The Expansion of
Life without Parole Sentences in the United States, Fed. Sent'g.
Rep. 23(1) (2010), 2010 WL 6681093 at *30 ("In many other
industrialized nations, serious offenders are typically released
after a maximum prison term of no more than thirty years. For
instance, in Spain and Canada, the longest sentence an offender
can receive is twenty-five or thirty years. In Germany, France,
and Italy, LWOP has been declared unconstitutional. In the United
Kingdom, it is allowable, but used quite sparingly; according to
a recent estimate, only twenty-three inmates were serving this
sentence. In Sweden, parole-ineligible life sentences are
permissible, but never mandatory. The Council of Europe stated in
1977 that 'it is inhuman to imprison a person for life without the
hope of release,' and that it would 'be compatible neither with
the modern principles on the treatment of prisoners . . . nor with
the idea of the reintegration of offenders into society.'")
(footnotes omitted).
41

Id.

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Additional Observations
The analysis could stop here.

But because this is such

a rare case, a few additional observations are in order.
1.

Direct Comparison to Other Cases
A direct comparison of Rivera-Ruperto's offense and its

sentence to offenses and their sentences that the Supreme Court
held constitutional is enlightening.
See supra, Section I.C.3.

There are five such cases.

Four of these cases involve recidivists

-- and the Supreme Court weighed the recidivism heavily in its
proportionality analysis.
career

criminal,

another

appropriate sentence.

See id.
important

See id.

The fifth case involved a
factor

in

determining

the

However, Rivera-Ruperto is neither

a recidivist nor a career criminal.
who has not led a life of crime.

He is a first-time offender

I therefore place his crime on

one side of the scales -- without adding the weight of recidivism
or a career of crime -- and his sentence on the other.

And the

weight of the sentence dwarfs the weight of his offense.
Such a direct comparison also holds if the present case
is compared to cases from other circuits.

The Government, in its

28j letter, has provided this court with eleven cases of sentences
from 55 to 186 years given under § 924(c).42

42

The Government notes

To wit: United States v. Wiest, 596 F.3d 906 (8th Cir.
2010); United States v. McDonel, 362 F. App'x 523 (6th Cir. 2010);
United States v. Walker, 437 F.3d 71 (3d Cir. 2007); United States
v. Watkins, 509 F.3d 277 (6th Cir. 2007); United States v. Khan,
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that these lengthy sentences were "based largely on recidivist
violations of § 924(c)."

In fact, only three of these cases

concerned recidivist offenders; six involved career criminals; the
final one involved terrorists who were involved in, inter alia,
planning the attacks on 9/11.

It is telling indeed that in

providing this court with cases in which sentences of comparable
length to Rivera-Ruperto's weathered Eighth Amendment challenges,
the Government has presented this court with such grave offenses
as:

461 F.3d 477 (4th Cir. 2006); United States v. Angelos, 433 F.3d
738 (10th Cir. 2006); United States v. Hungerford, 465 F.3d 1113
(9th Cir. 2006); United States v. Beverly, 369 F.3d 516 (6th Cir.
2004); United States v. Marks, 209 F.3d 577 (6th Cir. 2000); United
States v. Arrington, 159 F.3d 1069 (7th Cir. 1998). The Government
also cites United States v. Hernández-Soto, No. 12-2210 (1st Cir.
Aug. 19, 2015); although Hernández-Soto did involve a lengthy
sentence, there was no Eighth Amendment challenge in that case,
and I therefore do not consider it here. Finally, the Government
cites United States v. Polk, 546 F.3d 74 (1st Cir. 2008), a case
in which this court rejected an Eighth Amendment challenge to a
fifteen-year sentence imposed under 18 U.S.C. § 2251(e).
The
defendant in Polk had engaged in online conversation with a person
he thought was a 13-year-old girl, and he pressured her to take
sexually explicit photographs of herself and to send them to him.
In addition, "The presentence investigation report told a seamy
story: it revealed an earlier conviction for aggravated sexual
assault on a toddler, sexual involvement with teenage girls on at
least two occasions, and yet another series of sexually charged
computer chats with a minor. The defendant conceded these facts
. . . ." Polk, 546 F.3d at 75. I see no difficulty in reconciling
the proposition that Polk's sentence of 15 years did not violate
the Eighth Amendment with the proposition that Rivera-Ruperto's
sentence of, effectively, LWOP, does violate the Eighth Amendment.

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

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Seven

bank

robberies

Page: 66

(in

Date Filed: 01/13/2017

four

of

which

a

Entry ID: 6062260

firearm

was

brandished) by "a repeat bank robber whose criminal record
reflects a life of violent crime interrupted only by terms of
imprisonment."


Arrington, 159 F.3d at 1073.

A defendant who "was convicted of six separate robberies,
each

of

which

involved

the

brandishing

of

a

firearm."

Watkins, 509 F.3d at 283. Although a first-time offender, the
defendant

"and/or

his

accomplices

entered

the

homes

of

victims by force and threatened to seriously harm or kill not
only the victims, but, in multiple cases, their spouses and
small children."


Id.

Defendants who were involved in the planning of the terrorist
attack on 9/11 and who were convicted on "various counts
related to a conspiracy to wage armed conflict against the
United States and a conspiracy to wage armed conflict against
a country with whom the United States is at peace."

Khan,

461 F.3d at 83.
Thus, the Government confirms that when long sentences
are applied to serious offenses by recidivists, career criminals,
or terrorists, the Eighth Amendment does not protect the offenders,
for the severe punishment is not grossly disproportionate to the
grave crimes.

But Rivera-Ruperto is a first-time offender; he is

no career criminal; and he is no terrorist.

Note that even in the

case of recidivist, but minor, offenses, the punishment may violate
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the Eighth Amendment.

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See Ramírez v. Castro, 365 F.3d 755 (9th

Cir. 2004) (holding that a sentence of 25 years to life for a third
shoplifting offense violated the Eighth Amendment).
2.

Penological Goals
There is also a suggestion in the case law that courts

may consider penological goals in their analysis, specifically:
deterrence,

retribution,

Ewing, 538 U.S. at 24.

rehabilitation,

and

incapacitation.

As for deterrence, harsh punishment can

have a deterrent effect, but deterrence alone cannot justify
disproportionate punishment: "The inquiry focuses on whether, a
person deserves such punishment, not simply on whether punishment
would serve a utilitarian goal. A statute that levied a mandatory
life sentence for overtime parking might well deter vehicular
lawlessness, but it would offend our felt sense of justice".
Rummel,

445

U.S.

at

288

(Powell,

J.,

dissenting).

As

for

retribution, it is not clear how Rivera-Ruperto has caused any
injury -- for the transaction was a sham -- but even if one ignores
that obstacle, Rivera-Ruperto clearly caused less of an injury
than those who receive LWOP under federal law, or, for that matter,
than those who receive a lesser punishment under federal law.

See

supra, Section II.A. Indeed, had Rivera-Ruperto been a drug dealer
himself, and transacted a vast quantity of real drugs in a single
transaction to which he brought a gun, he would undoubtedly have
received a much lower sentence.

Id.

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Rehabilitation is clearly

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not served here, because the current sentence means that the law
has judged Rivera-Ruperto to be beyond rehabilitation -- something
that may be understandable in the case of recidivists who have
demonstrated that punishment does not change their ways -- but it
is troubling indeed to say that a first-time offender will not be
given a chance to learn from his mistakes.

Finally, as to

incapacitation, Rivera-Ruperto does not present such a danger to
society that society needs to be protected from him forever.
This analysis of penological goals highlights another
facet of the present case that deserves pause.

Rivera-Ruperto's

offenses involved a sham drug transaction, at which sham drugs
were transacted.

"Proportionality--the notion that the punishment

should

crime--is

fit

the

inherently

penological goal of retribution."

a

concept

tied

to

the

Ewing, 538 U.S. at 31 (Scalia,

J., concurring). But Rivera-Ruperto did no injury, and retribution
is therefore not in order.
analysis.

This affects the proportionality

For the purposes of proportionality, participation in

a sham drug deal and a real drug deal weigh differently, because
retribution applies in the latter, but not in the former.

That is

not to say that when a sentence is given out for a sham drug deal
as if it were a real drug deal, then that sentence necessarily
violates the Eighth Amendment.
disproportionate,

it

would

For while such a sentence might be
not

necessarily

be

disproportionate" so as to violate the Eighth Amendment.

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"grossly
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the length of a sentence for a sham deal is multiplied, so is its
disproportionality.
3.

This is simply arithmetic and common sense.

The Legislature's Judgment
The three-step analysis already incorporates due respect

for

the

judgment

of

the

legislature

as

to

the

severity

of

penalties, and, as shown above, Rivera-Ruperto's case passes that
analysis.
deference,

Because the judgment of the legislature deserves great
however,

it

is

worth

pointing

out

that,

on

the

particular facts of this case, I am not questioning the judgment
of the legislature.

Rather, § 924(c), as the late Chief Justice

Rehnquist pointed out, presents a good example of "unintended
consequences" of legislative action.43

Indeed, § 924(c) was the

result of a floor amendment (so there is no legislative history)
passed by a legislature that wanted to appear tough on gun crime
soon after the assassinations of Robert Kennedy and Martin Luther
King, Jr.44

Not only were the minimums in that law much lower than

they have become since, but -- crucially -- the law was understood
as a recidivist statute for a good 25 years.

It was not until

43

William H. Rehnquist, Luncheon Address (June 18, 1993),
in U.S. Sentencing Comm'n., Proceedings of the Inaugural Symposium
on Crime and Punishment in the United States, 286 (1993).
44

Judge Paul Cassell, Statement on Behalf of the Judicial
Conference of United States from U.S. District Judge Paul Cassell
before the House Judiciary Committee Subcommittee on Crime,
Terrorism, and Homeland Security, 2007 WL 3133929, Fed. Sent'g.
Rep. 19(5) (2007) at *347.

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Deal v. United States, 508 U.S. 129 (1993), that the statute became
applied the way it is today -- not as a recidivist statute, but
rather as one that requires stacking of mandatory minimums on
first-time and recidivist offenders alike.

Not only is this court

generally cautious to infer anything from Congressional inaction,
but in this case, it would not even make sense to try.
Congress's inaction cuts both ways:

For

for the first 25 years after

§ 924(c) was enacted, the statute applied to recidivists only;
after Deal, that changed -- but Congress did not act on either
understanding of the statute.

Furthermore, as has been pointed

out countless times, applications of § 924(c) such as in the case
before us today contravene the intent of Congress in many ways:
most importantly, § 924(c) has led to significant sentencing
disparity, directly contradicting the intent behind the major
sentencing reform of the 1980s. See, e.g., Stephen Breyer, Federal
Sentencing Guidelines Revisited, 1999 WL 730985, Fed. Sent'g. Rep.
11(4)(1999).

This is yet another facet of the present case that

distinguishes it from this court's decision in, for instance, Polk.
See supra, n.20.

In that case, this court was faced with a harsh

sentence -- but that sentence was clearly so intended by Congress,
Congress had clearly resolved that the offense in question deserved
that harsh penalty.

But in the present case, this court is faced

not with a Congressional assessment of the gravity of this offense,

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but rather with an unintended consequence of a statute hastily
implemented and judicially altered.
III.

Conclusion

The present case is "hen's-teeth rare".
at 76.

It may very well be even rarer than that.

Polk, 546 F.3d
I would hold

that Rivera-Ruperto's sentence violates the Eighth Amendment.
Indeed, the present case is so rare that it is distinguishable
from the cases in which the Supreme Court rejected Eighth Amendment
challenges to sentences for a term of years (already rare cases),
and it is also distinguishable from cases the Government cited in
which

other

circuits

rejected

Eighth

Amendment

sentences under § 924(c) (also rare cases).

challenges

to

Never before has a

first-time offender who has not dedicated his life to crime been
condemned to spend his entire life in prison for a transgression
such

as

Rivera-Ruperto's,

not

even

in

cases

in

which

the

transgression was real -- and Rivera's-Ruperto's transgression is
fictitious.
The

Government

has

effectively

asked

this

court

to

pronounce the Eighth Amendment dead for sentences for a term of
years.

I respectfully refuse to join in this pronouncement.

"Unless we are to abandon the moral commitment embodied in the
Eighth

Amendment,

proportionality

effectively obsolete."

review

must

never

become

Graham, 560 U.S. at 85 (Stevens, Ginsburg,

Sotomayor, JJ., concurring).

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