US v. Rivera-Ruperto

Filing

OPINION issued by Juan R. Torruella (dissenting in part), Appellate Judge; Kermit V. Lipez, Appellate Judge and Rogeriee Thompson, Appellate Judge. Published. [13-2017, 13-2047, 13-2072]

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Document: 00117105534

Page: 1

Date Filed: 01/13/2017

Entry ID: 6062247

United States Court of Appeals
For the First Circuit
Nos. 13-2017, 13-2047, 13-2072
UNITED STATES,
Appellee,
v.
WENDELL RIVERA-RUPERTO, a/k/a Arsenio Rivera,
MIGUEL SANTIAGO-CORDERO,
DAVIEL SALINAS-ACEVEDO,
Defendants, Appellants.

APPEALS FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF PUERTO RICO
[Hon. Carmen Consuelo Cerezo, U.S. District Judge]

Before
Torruella, Lipez, and Thompson,
Circuit Judges.

H. Manuel Hernández for appellant Wendell Rivera-Ruperto.
Ignacio Fernández de Lahongrais for appellant Daviel SalinasAcevedo.
Camille Lizarribar-Buxó on brief for appellant Miguel
Santiago-Cordero.
Robert J. Heberle, Attorney, Public Integrity Section,
Criminal Division, U.S. Department of Justice, with whom Juan
Carlos Reyes-Ramos, 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.

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THOMPSON, Circuit Judge.

Date Filed: 01/13/2017

Entry ID: 6062247

In this appeal, Defendant-

Appellants Wendell Rivera-Ruperto, Daviel Salinas-Acevedo, and
Miguel Santiago-Cordero challenge various aspects of their trial
and sentencing.

For Rivera-Ruperto, this was his second of two

trials, which were presided over by different district judges.
Having separately addressed Rivera-Ruperto's challenges from the
first trial in a decision simultaneously released herewith, we
address in this opinion Rivera-Ruperto's challenges, as well as
those of Salinas-Acevedo and Santiago-Cordero, as to the second
trial only.
During trial, all three defendants were convicted of
various federal drug and firearms-related crimes for participating
in drug deals that were staged as a part of the FBI sting operation
"Operation Guard Shack," about which we say more in a bit.

As a

result of the convictions, each was sentenced to multiple years of
imprisonment.

In

the

present

appeal,

Rivera-Ruperto

raises

similar challenges, which we detail momentarily, to those he raised
in his appeal of his first trial and sentencing.

As for Salinas-

Acevedo, he argues the district court erred in preventing him from
presenting an entrapment defense.

Santiago-Cordero presses a

similar argument, challenging the judge's refusal to give an
entrapment jury instruction, and also appeals the district court's
denial of his post-verdict motion for acquittal.
For the reasons stated below, we affirm.

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OVERVIEW
We begin with a broad overview of the facts, and later
return to the specific details of the case as they relate to the
individual defendants' arguments.
Operation Guard Shack, as we have explained in previous
decisions,1 was a large-scale investigation mounted by the FBI over
several years in order to root out police corruption throughout
Puerto Rico.

Each of the stings followed a similar pattern.

Undercover FBI informants recruited police officers to provide
armed security at drug deals staged by the FBI.

The deals took

place at FBI-monitored apartments wired with hidden cameras, and
involved undercover officers posing as sellers and buyers of sham
cocaine. In exchange for their armed security services, the police
officers were paid about $2,000 per deal.
Rivera-Ruperto, Salinas-Acevedo, and Santiago-Cordero
provided armed security at several of these Operation Guard Shack
sham drug deals between March and September of 2010.

Rivera-

Ruperto, who was not a police officer (but who was recruited
because

he

misrepresented

himself

to

the

FBI's

undercover

informant as a prison corrections officer) provided armed security

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).

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at six deals, which took place on April 9, April 14, April 27,
June 9, June 25, and September 16 of 2010.

Salinas-Acevedo and

Santiago-Cordero, who were both police officers, participated in
one deal each, on March 24, 2010, and July 8, 2010, respectively.
The government charged the three defendants with one
count each of conspiracy and attempted possession with intent to
distribute a controlled substance, as well as possession of a
firearm in relation to a drug trafficking crime.

(Various other

co-defendants were also charged, but their cases are not before
us.)

In this indictment, Rivera-Ruperto was charged for his

participation in the April 9 deal only.

For his participation in

the five later deals, Rivera-Ruperto had already been indicted
separately, tried before a different district judge, and found
guilty.

The first judge sentenced Rivera-Ruperto to 126-years and

10-months' imprisonment.
Several months after Rivera-Ruperto's first trial, he,
Salinas-Acevedo, and Santiago-Cordero were tried together in a
second proceeding, which is the subject of this appeal.

The jury

found Rivera-Ruperto guilty of all charges, and Salinas-Acevedo
and Santiago-Cordero guilty of the conspiracy and firearms counts
(it did not reach a verdict for either of them on the attempted
possession

count).

After

separate

sentencing

hearings,

the

district judge sentenced Rivera-Ruperto to 35-years imprisonment
to be served consecutively with his first sentence, resulting in

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a combined prison sentence from Rivera-Ruperto's two trials that
totaled 161 years and 10 months.

Salinas-Acevedo and Santiago-

Cordero were each sentenced to 15-years and 1-month imprisonment.
The
challenges

defendants

various

timely

aspects

of

appealed.

the

trial

Rivera-Ruperto

and

sentencing,

and

Salinas-Acevedo and Santiago-Cordero of the trial only. We discuss
below each defendant in turn, beginning with Rivera-Ruperto.
DISCUSSION
I. RIVERA-RUPERTO
As we have previously noted, we issue today a companion
decision to this case affirming the district court in RiveraRuperto's first trial and sentencing.
here

are

similar

to

those

he

Rivera-Ruperto's challenges

raised

in

that

first

appeal.

Specifically, Rivera-Ruperto argues that the district court in
this second case committed reversible errors when it: (1) failed
to conduct a sua sponte inquiry to determine whether Rivera-Ruperto
had received ineffective assistance of counsel during the pleabargaining stage; (2) gave erroneous jury instructions; (3) did
not reduce his sentence on account of sentencing manipulation by
the government; and (4) sentenced him to a grossly disproportionate
sentence in violation of the Eighth Amendment.

For the reasons we

explain, each of these challenges fails in this second appeal, as
well.

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A.

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Lafler Claim
Rivera-Ruperto reprises a Lafler challenge that he made

(and lost) in his first appeal, in which he argues that he received
ineffective

assistance

of

counsel

during

the

plea-bargaining

phase. See Lafler v. Cooper, 132 S. Ct. 1376, 1384 (2012) (holding
that a defendant's Sixth Amendment right to competent counsel
extends to the plea-bargaining process).

Before getting to his

arguments, we give a brief recounting of what happened below.
1.

Background

We set what is quite the complicated stage by again
reminding the reader that Rivera-Ruperto eventually stood two
trials, which were presided over by different district judges.
Before the first trial began, Rivera-Ruperto was represented by
court-appointed attorney Jose Aguayo ("Aguayo"), who remained his
lawyer throughout the plea-bargaining stage.
Aguayo attempted to negotiate a plea deal for all of
Rivera-Ruperto's charges across the six sham drug deals (though
Rivera-Ruperto had been indicted separately for the charges). When
the negotiations resulted in no plea deal, the first case proceeded
toward

trial,

this

time

with

Rivera-Ruperto

represented

by

different court-appointed counsel.
Three days before that first trial was set to begin,
Rivera-Ruperto's second attorney filed a Lafler motion, alleging

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that Aguayo had provided ineffective assistance of counsel at the
plea-bargaining stage.

He argued that but for Aguayo's deficient

performance, Rivera-Ruperto would have taken a 12-year plea deal
that the government had previously offered during negotiations,
and he requested that the court order the government to re-offer
that 12-year deal.
On the morning of the day the first trial was scheduled
to begin, the presiding judge held an evidentiary hearing on the
issue.
the

After considering the testimony and documentary evidence,

judge

denied

counsel claim.

Rivera-Ruperto's

ineffective

assistance

of

For reasons that we explain in detail in our

companion decision and will not rehash here, we have already
affirmed the judge's denial of Rivera-Ruperto's Lafler claim as it
pertains to his first trial.
Some

months

after

the

first

trial

and

sentencing,

Rivera-Ruperto, represented by the same attorney, stood trial a
second

time

for

the

charged

offenses

participation in the April 9 deal only.

stemming

from

his

At no time did trial

counsel request that the second judge consider the Lafler argument
Rivera-Ruperto

had

raised

and

lost

before

the

first

judge.

Therefore, no ineffective assistance of counsel claim was raised
by counsel or ruled upon by the judge in this second case.
2.

Analysis

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On

appeal,

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Rivera-Ruperto

acknowledges

that

Entry ID: 6062247

counsel

during his second trial never raised the Lafler issue, but he
argues that the trial judge should nevertheless have made a sua
sponte

inquiry

and

independent

assistance of counsel claim.

ruling

on

the

ineffective

The judge's failure to do so, he

claims, was reversible error.2
Rivera-Ruperto never raised the Lafler issue before the
second presiding judge, and we assume his claim was forfeited and
not waived.

We thus review the judge's purported failure to make

a sua sponte inquiry on the ineffective assistance of counsel claim

2

The government raises a threshold argument that, because
Rivera-Ruperto had already obtained a ruling on the Lafler issue
in the first case, he was collaterally estopped from raising an
identical issue in his second trial.
Collateral estoppel, often referred to as issue preclusion,
traditionally barred civil litigants from relitigating an issue
that had already been decided in an earlier action. But it has
also become an "established rule of federal criminal law," and "is
a part of the Fifth Amendment's guarantee against double jeopardy."
United States v. Collazo-Aponte, 216 F.3d 163, 198 (1st Cir. 2000),
vacated on other grounds by 532 U.S. 1036 (2001). As such, our
case law has permitted the use of collateral estoppel in criminal
cases -- at least insofar as it is invoked by the defendant to
prevent the government from relitigating a previously-decided
issue. See id.
The parties disagree over whether collateral estoppel may be
used here, by contrast, offensively against Rivera-Ruperto.
Indeed, we know of no case in our circuit, and the government
points us to none, in which we have used collateral estoppel to
prevent a criminal defendant from raising an issue, as the
government would have us do in this case. We need not decide this
issue today, however, and will not. As we explain, even if we
assume, favorably to Rivera-Ruperto, that he is not collaterally
estopped from raising his Lafler claim, the claim still fails.

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for plain error.
74

(1st

Cir.

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United States v. Sánchez-Berríos, 424 F.3d 65,

2005)

("[A]

waived

issue

ordinarily

cannot

be

resurrected on appeal, whereas a forfeited issue may be reviewed
for plain error".).
Reversal under plain error review is only proper if:
(1) an error occurred; (2) it was obvious; (3) it affects the
defendant's

substantial

fundamental

to

rights;

threaten

the

reputation of the proceedings.

and

fairness,

it

is

sufficiently

integrity

or

public

United States v. Delgado-Marrero,

744 F.3d 167, 184 (1st Cir. 2014).
in meeting these requirements.

(4)

Rivera-Ruperto cannot succeed

Even assuming that he clears the

first three of the plain error review hurdles, Rivera-Ruperto
cannot clear the fourth, because he cannot show that the judge's
purported

error

was

sufficiently

fundamental

to

threaten

the

fairness, integrity or public reputation of the proceedings.
In order to meet this fourth requirement, Rivera-Ruperto
would need to show that if the judge had made a sua sponte inquiry
into his ineffective assistance of counsel claim, she would indeed
have found that Rivera-Ruperto had received ineffective assistance
at

the

plea-bargaining

appropriate relief.

stage,

and

was

therefore

entitled

to

But, for reasons we explain in great detail

in our companion decision to this case, and which we will not
belabor here, we have already determined, on de novo review, that
Rivera-Ruperto was not entitled to Lafler relief, as he cannot

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meet the two-part ineffective assistance of counsel test laid out
in Strickland v. Washington, 466 U.S. 668, 687 (1984). See Lafler,
132 S. Ct. at 1376.

Specifically, Rivera-Ruperto is unable to

show either that Aguayo's performance was defective or that, even
if defective performance were to be assumed, it prejudiced him.
Thus, any claimed error on the second judge's part in failing to
conduct a sua sponte Lafler inquiry did not threaten the fairness
or integrity of Rivera-Ruperto's proceedings, and reversal on this
ground is not proper.
B.

Alleyne Issue
We

move

on

to

Rivera-Ruperto's

appeal

of

the

jury

instructions at his second trial, the only one of Rivera-Ruperto's
claimed errors that we have not also addressed in our companion
decision.

Rivera-Ruperto

challenges

the

jury

instructions

regarding the firearms charges only, so we focus our discussion
accordingly.
1.

First, a discussion of what happened below.
Background

Before we begin, we pause to remind the reader that at
his first trial, among other offenses, Rivera-Ruperto had been
charged with and convicted of one count of possession of a firearm
in relation to a drug trafficking crime for his participation in
each of five sham drug deals (which occurred on April 14, April
27, June 9, June 25, and September 16 of 2010).

Under 18 U.S.C.

§ 924(c)(1)(A), a defendant who is convicted of possession of a

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firearm in relation to a drug trafficking crime is subject to a
mandatory minimum sentence of 5-years imprisonment on the first
conviction, and then 25-years imprisonment for every subsequent
conviction, id. § 924(c)(1)(C)(i), to be served consecutively, id.
§ 924(c)(1)(D)(ii).

Accordingly, following the trial, the first

district judge sentenced Rivera-Ruperto to a total of 105 years
imprisonment for his firearms convictions (5 years for the first
§ 924(c) conviction, and 25 for each of the subsequent four
convictions).
At the second trial, Rivera-Ruperto was again tried,
among other offenses, for possession of a firearm in relation to
a drug trafficking crime, this time for his participation in the
April 9, 2010 drug deal only.

Notable for Rivera-Ruperto's

purposes, the government did not introduce at the second trial any
evidence of Rivera-Ruperto's prior § 924 convictions from his first
trial.

In addition, while the judge instructed the jury as to the

elements of the firearms offense, neither the jury instructions
nor the verdict form included prior § 924 convictions as an
"element" of the offense, or otherwise made any mention of RiveraRuperto's prior convictions.3

After deliberating, the jury found

Rivera-Ruperto guilty of all counts.

3

The verdict form, which Rivera-Ruperto did not object to,
simply stated: "We, the Jury, find defendant WENDELL RIVERA RUPERTO
___________ (GUILTY/NOT GUILTY) as charged in Count Eighteen of
the Indictment."

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Prior to sentencing, Rivera-Ruperto filed a sentencing
memorandum in which he argued that -- notwithstanding his five
previous § 924 convictions from the first trial -- the judge should
impose the 5-year mandatory minimum sentence for a first-time
conviction under the firearms statute, and not the 25-year minimum
for subsequent convictions.

Rivera-Ruperto argued that the judge

could not impose the "enhanced" mandatory minimum because the jury
had not made a beyond-a-reasonable-doubt finding as to his prior
§ 924 convictions.
The judge disagreed, denying the request in a written
order prior to sentencing.

After a hearing, the judge imposed the

25-year

for

minimum

sentence

a

subsequent

§

924

conviction.

Rivera-Ruperto now appeals.
2.

Analysis

Because the sentencing memorandum Rivera-Ruperto filed
before the district court preserved his Alleyne challenge, our
review of his argument on appeal is de novo.4

See Delgado-Marrero,

744 F.3d at 184.
In order to explain Rivera-Ruperto's argument, we must
first give a bit of background on the relevant case law.

At the

Count Eighteen of the Indictment charged Rivera-Ruperto with
"knowingly possess[ing] a firearm in furtherance of a drug
trafficking crime as defined in Title 18, United States Code,
Section 924(c)(2)," but made no mention of prior convictions under
18 U.S.C. § 924.
4

Jury instruction challenges generally must be preserved at
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time of Rivera-Ruperto's second trial, the rule was (and still is,
as we explain in a moment) that "[o]ther than the fact of a prior
conviction, any fact that increases the penalty for a crime beyond
the prescribed statutory maximum" is an element of the offense to
be found by a jury beyond a reasonable doubt.

Apprendi v. New

Jersey, 530 U.S. 466, 490 (2000) (emphasis added).

In making this

exception for prior convictions in Apprendi, the Supreme Court
deliberately left undisturbed its holding in Almendarez-Torres v.
United States, 523 U.S. 224, 226-27 (1998), which permitted the
use of prior convictions to enhance sentences without a finding by
the jury.
Between

Rivera-Ruperto's

trial

and

sentencing,

the

Supreme Court decided Alleyne v. United States, 133 S. Ct. 2151,
2155 (2013), in which it held that the Apprendi rule applied not
only to facts that increase the mandatory maximum sentence, but
also to those that increase the mandatory minimum (thus overruling
its prior holding in Harris v. United States, 536 U.S. 545, 568
(2002), which had limited Apprendi to the former).

The Supreme

Court explicitly stated, however, that its decision would leave
untouched

Almendarez-Torres's

convictions.

"narrow

exception"

for

prior

Alleyne, 133 S. Ct. at 2160 n.1.

trial, but a defendant may preserve his challenge to an
instructional Apprendi/Alleyne error by objecting at sentencing.
See United States v. Pizarro, 772 F.3d 284, 296 (1st Cir. 2014).
The government also concedes that our review here is de novo.

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Despite this language in Alleyne itself, Rivera-Ruperto
argues before us that Alleyne made Almendarez-Torres inapplicable
to his case.

He seems to argue that, because Alleyne expanded the

Apprendi umbrella, bringing facts that increase mandatory minimums
under its shelter, we should, in keeping with the spirit of
Alleyne, limit Almendarez-Torres to its facts and determine that
only prior convictions that increase the prescribed maximum are
exempt from the Apprendi rule that such facts be found by a jury.
Because his prior convictions increased the prescribed minimum,
Rivera-Ruperto

argues,

they

should

be

subject

to

Alleyne's

requirement that they be found by a jury beyond a reasonable doubt.
But this is not the law.

As we have already explained,

this was not the Supreme Court's holding in Alleyne.

Moreover, we

have already rejected, in a post-Alleyne case, the argument that
prior convictions must be proven to a jury beyond a reasonable
doubt.

See United States v. Rodriguez, 759 F.3d 113, 122 (1st

Cir. 2014) (holding that the jury was not required to make a
finding

as

to

the

defendant's

Almendarez-Torres remained good law).
C.

prior

convictions

because

We therefore find no error.

Sentencing Challenges
Rivera-Ruperto's remaining two challenges concern his

sentence.

He argues, as he did in his appeal from the first trial,

that the government engaged in improper sentencing manipulation,
and that his sentence across the two trials, for a combined 161-

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years and 10-months' imprisonment, violates the Eighth Amendment's
prohibition on cruel and unusual punishment.

In raising these

arguments in the present appeal, Rivera-Ruperto incorporates by
reference the sections of his brief from his appeal in the first
trial.

As we have already discussed these arguments in detail in

our companion decision, we keep our recounting of what happened
concise.
1.

Background

At the first trial, the jury found Rivera-Ruperto guilty
of five counts each (one for each of the five charged drug deals)
of conspiracy and attempted possession with intent to distribute
5 kilograms or more of a controlled substance and of possession of
a firearm in relation to a drug trafficking crime.

It also found

Rivera-Ruperto guilty of one count of possession of a firearm with
an obliterated serial number.
At sentencing, Rivera-Ruperto argued that the FBI's use
of "large" quantities of sham cocaine at each of the drug deals,
its request that he bring a firearm to each of the deals, its
decision to allow him to participate in multiple deals, and its
decision to charge him separately for each of the deals all
constituted improper sentencing manipulation because, he claimed,
the government made those choices for the sole purpose of exposing
him to an enhanced sentence.

The first district judge disagreed,

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and sentenced Rivera-Ruperto to 126 years and 10 months for the
crimes.
At his second trial, Rivera-Ruperto was again found
guilty, this time of one count each of three crimes (for the
remaining

April

9

drug

deal

only):

conspiracy

and

attempted

possession with intent to distribute 5 kilograms or more of a
controlled substance, and possession of a firearm in relation to
a drug trafficking crime.
After
Ruperto's

a

sentencing

counsel

did

not

hearing,
raise

a

during

which

sentencing

Rivera-

manipulation

objection, the second district judge sentenced Rivera-Ruperto to
the statutory minimum of 10-years imprisonment for the conspiracy
and

attempt

counts

and

the

statutory

imprisonment for the firearms count.

minimum

of

25-years

Rivera-Ruperto was thus

sentenced to a total of 35-years imprisonment, to be served
consecutively to his 126-year and 10-month sentence from the first
trial.
2.

Sentencing Manipulation

Because

Rivera-Ruperto

did

not

raise

a

sentencing

manipulation challenge before the second district judge, we review
for plain error.5

See Sánchez-Berríos, 424 F.3d 65 at 78.

5

Rivera-Ruperto did raise his sentencing manipulation
argument during his first sentencing hearing before the first
district judge, and it would therefore be reasonable to treat the
sentencing manipulation argument as altogether waived as to his
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Rivera-Ruperto argues that the government engaged in
sentencing manipulation by using unnecessarily high quantities of
sham drugs during the deals, requiring Rivera-Ruperto to bring a
firearm with him to each of the deals, and then allowing him to
participate in a "seemingly endless" number of those deals.

We

need not tarry in our consideration of Rivera-Ruperto's sentencing
manipulation argument here.
in

detail

why

manipulation

In our companion decision, we explain

Rivera-Ruperto's

argument

fails

fact-determinative

under

a

clear-error

sentencing
standard

of

review. In renewing his challenge as to this second trial, RiveraRuperto has added no new argument, choosing merely to incorporate
by reference the sections of his brief from his first appeal.
Because Rivera-Ruperto has adopted his briefing from the first
case wholesale, the only difference in our review here is that the
more rigorous plain-error standard applies.

Given that Rivera-

Ruperto's sentencing manipulation challenge failed under the less
exacting standard in the first case, it also fails here.
3.

Eighth Amendment

The same is true of Rivera-Ruperto's final challenge:
his argument that his total sentence from the two trials of 161years and 10-months' imprisonment violates the Eighth Amendment's

second sentence. The government, however, does not argue waiver
in its brief. Thus, favorably to Rivera-Ruperto, we review for
plain error.

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prohibition on cruel and unusual punishment.

Entry ID: 6062247

Here, Rivera-Ruperto

again adopts by reference the Eighth Amendment section of his brief
in the first appeal, which fails for the reasons we have already
explained in our decision in that case.

For the reasons stated in

our companion opinion, Rivera-Ruperto's sentence is affirmed.
II. SALINAS-ACEVEDO
We turn now to Salinas-Acevedo's appeal.

As we noted

above, Salinas-Acevedo was indicted on charges of conspiracy to
distribute and attempted possession with the intent to distribute
more than 5 kilograms of cocaine, as well as of possession of a
firearm in furtherance of a drug crime, for his participation in
one Operation Guard Shack deal on March 24, 2010.

The jury found

Salinas-Acevedo guilty of the conspiracy and firearm counts, but
did not reach a verdict as to the attempted possession count.
Salinas-Acevedo was sentenced to a total of 15-years and 1-month
imprisonment.
Salinas-Acevedo raises just one argument on appeal.

He

argues that the district court erred in preventing him from
presenting an entrapment defense at trial.

We begin with a

discussion of what happened below.
A.

Background
1.
On

Lead-Up to the March 24 Deal
March

24,

2010,

fellow

police

officers

Salinas-

Acevedo, Alwin Camacho ("Camacho"), and Israel Rullán-Santiago

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("Rullán-Santiago")6 provided armed security at an Operation Guard
Shack drug deal.

What Salinas-Acevedo did not know at the time

was that Camacho was working undercover as an FBI informant to
recruit corrupt police officers for Operation Guard Shack.
Camacho had targeted Rullán-Santiago after he heard
Rullán-Santiago bragging around the station that he knew drug
traffickers and was "basically a delinquent using up the uniform."
It was Rullán-Santiago who, in turn, recruited his friend SalinasAcevedo. Both Rullán-Santiago and Camacho were aware that SalinasAcevedo had a daughter and was expecting another child, and that
he was in a difficult financial situation.
Originally, Salinas-Acevedo was supposed to participate
in a drug transaction that had been planned for March 10, 2010.
But,

according

to

a

recorded

telephone

conversation

between

Rullán-Santiago and Camacho on the night before that deal, SalinasAcevedo, seemingly referring to his child, backed out at the last
minute, telling Rullán-Santiago, "Sorry, it's gonna be difficult
for me because of the little girl and the like."

Hearing that

Salinas-Acevedo would not make it to the deal, Camacho postponed
the scheduled transaction.
Shortly thereafter, Camacho was also recorded talking to
Carlos Méndez-Pérez ("Méndez-Pérez"), yet another police officer

6

Rullán-Santiago was one of the co-defendants in this case
below, but is not a party to this appeal.

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who would himself participate in Operation Guard Shack and be
charged separately in a different case.

During the conversation,

Camacho

Camacho

brought

up

Salinas-Acevedo.

asked,

"[S]ince

you're buddies with Salinas, what do you think about Salinas?"

He

went on to say, "Because, um, Rullán approached him and later he
gave me excuses that his daughter . . . ."

Camacho told Méndez-

Pérez that Rullán-Santiago had told him that Salinas-Acevedo was
"willing to do anything and he's broke."
Camacho also told Méndez-Pérez that he had directed
Rullán-Santiago not to "bring up that topic with [Salinas-Acevedo]
anymore."

But later in the conversation, Camacho told Méndez-

Perez to talk to Salinas-Acevedo and have him "come by" to see
him.

In response, Méndez-Pérez told Camacho that he would stop by

Salinas-Acevedo's house.

Camacho instructed Méndez-Pérez to find

out what days Salinas-Acevedo "ha[d] available," but also directed
Méndez-Pérez, "[I]f he gives you a lot of crap[;] . . . [t]his
isn't compulsory, this is for those who want to and know what it
is."
On
conversation

March
with

19,

2010,

in

Rullán-Santiago,

another
Camacho

recorded
directed

phone
Rullán-

Santiago to "get that guy that you tried to find last time," by
which he meant Salinas-Acevedo.

Rullán-Santiago responded, "[L]et

me see if, . . . if that dog is around here."

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Camacho replied,

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"Well, but let me know for sure, don't do the same shitty thing to
me like you did last week."
Three days later, Camacho, who by then presumably knew
Salinas-Acevedo had agreed to the job, called Rullán-Santiago to
"double check[]" that Rullán-Santiago and Salinas-Acevedo were
both on board for the upcoming March 24 drug deal.

In a not-

entirely-clear exchange, Camacho asked Rullán-Santiago, "You told
Salinas what it was, right, the devices?" Rullán-Santiago at first
told Camacho "Yes," but then laughed and told Camacho that SalinasAcevedo would "jump off the balcony when he sees [the drugs]."
The story ends, as we know, with the deal going down as
planned, with Rullán-Santiago and Salinas-Acevedo being arrested
and brought up on charges, and with Salinas-Acevedo standing
trial.7
2.

Lead-Up to Trial

Before trial, the government moved in limine to preclude
Salinas-Acevedo from raising an entrapment defense in his opening
statement.

The district court initially denied the motion, but

when the government filed a motion for reconsideration of the
order, the trial court ordered Salinas-Acevedo to proffer his
evidence supporting an entrapment defense.

7

Rullán-Santiago took a plea
sentenced to 19-years imprisonment.

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deal,

and

was

eventually

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Salinas-Acevedo proffered the following.

Entry ID: 6062247

First, he

asserted that, at all relevant times, Camacho had been aware of
Salinas-Acevedo's difficult financial situation because SalinasAcevedo had previously asked Camacho about part-time opportunities
at CompUSA, where Camacho worked as a part-time security guard,
and Camacho had told Salinas-Acevedo that he would let him know if
any opportunities opened up.

Second, Salinas-Acevedo submitted a

transcript

conversations

of

the

recorded

between

Camacho

and

Rullán-Santiago and Méndez-Pérez, which Salinas-Acevedo argued
showed that Camacho had targeted and incited Salinas-Acevedo into
participating in the sham drug deals.
Finally,

Salinas-Acevedo

alleged

that

he

had

been

wrongly induced into committing the crime because Rullán-Santiago
had told him that the March 24 transaction was a "legitimate
business transaction" involving the sale of diamonds, and that it
was only after he had arrived at the location that it was revealed
to him that it was a drug deal.

However, at the court's subsequent

prompting, Salinas-Acevedo conceded that he did not have any
evidence

that

the

government

(through

Camacho)

had

directed

Rullán-Santiago to tell Salinas-Acevedo that it was a legitimate
transaction, or that Camacho was otherwise responsible for the
alleged misinformation.
By sealed ex parte order, the court held that this was
an "insufficient basis to allow defendant Salinas to mention to

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the jury in opening statements a defense of entrapment," and
vacated its previous order denying the government's motion in
limine. Accordingly, Salinas-Acevedo was not permitted to mention
entrapment in his opening statement.
At trial, over the objections of Rivera-Ruperto and
Santiago-Cordero (our third co-defendant in this appeal, who we
will get to know better shortly), the district court declined to
give the jury an instruction on the entrapment defense.

Salinas-

Acevedo did not join in that objection to the jury instructions.
Salinas-Acevedo now appeals, arguing that the district court erred
in preventing him from raising an entrapment defense.
B.

Analysis
The

requested

government

argues

that

an

entrapment

instruction,

Salinas-Acevedo
nor

joined

in

neither
his

co-

defendants' jury instruction objection during trial, and that his
claim is therefore unpreserved and subject to plain error review.
See United States v. Guevara, 706 F.3d 38, 46 (1st Cir. 2013).
Salinas-Acevedo argues that our review is de novo, presumably on
a theory that his objection to the government's motion in limine
was sufficient to preserve his objection to being denied a jury
instruction on entrapment as well.

But even assuming, favorably

to Salinas-Acevedo, that the claim was properly preserved, the
argument still fails under de novo review.

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The judicially-created doctrine of entrapment exists "to
prevent 'abuse[]' of the 'processes of detection and enforcement
. . . by government officials' who might instigate an illegal 'act
on the part of persons otherwise innocent in order to lure them to
its commissions and to punish them.'"

United States v. Díaz-

Maldonado, 727 F.3d 130, 137 (1st Cir. 2013) (quoting Sorrells v.
United States, 287 U.S. 435, 448 (1932)) (alteration and omission
in original). A defendant seeking to present an entrapment defense
at trial must satisfy an "entry-level burden of production."
Sánchez-Berríos, 424 F.3d at 76.

He must produce "evidence which

fairly supports the claims" that: (1) the government agents not
only induced the crime but did so improperly, and (2) that he was
not already predisposed to commit the crime.

Id. at 76-77.

In determining whether a defendant has met this two-part
burden, a court "is to examine the evidence on the record and to
draw

those

inferences

as

can

reasonably

be

drawn

therefrom,

determining whether the proof, taken in the light most favorable
to the defense can plausibly support the theory of the defense."
United States v. Gamache, 156 F.3d 1, 9 (1st Cir. 1998).

If the

defendant succeeds and the defense is introduced at trial, it
becomes the government's obligation to prove beyond a reasonable
doubt that no entrapment occurred.
We

begin

by

examining

whether

Salinas-Acevedo

has

satisfied the improper inducement prong of his two-part burden.

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Because Salinas-Acevedo did not deal directly with Camacho -- the
"government agent" in this case, see United States v. Luisi, 482
F.3d 43, 53 (1st Cir. 2007) (explaining that an individual hired
as a government informant constitutes a government agent for
entrapment
middleman

purposes)

--

but

(Rullán-Santiago),

was

brought

into

Salinas-Acevedo

derivative theory of entrapment.

the

must

deal
rely

by

a

on

a

Under this theory, the conduct

of a middleman is only attributable to the government where:
(1) the government agent specifically targeted the
defendant in order to induce him to commit illegal
conduct; (2) the agent acted through the middleman after
other government attempts at inducing the defendant had
failed; (3) the government agent requested, encouraged,
or instructed the middleman to employ a specified
inducement, which could be found improper, against the
targeted defendant; (4) the agent's actions led the
middleman to do what the government sought, even if the
government did not use improper means to influence the
middleman; and (5) as a result of the middleman's
inducement, the targeted defendant in fact engaged in
the illegal conduct.
Luisi, 482 F.3d at 55.
Salinas-Acevedo
requirements.

satisfies

the

first

two

of

these

The recorded conversations proffered by Salinas-

Acevedo show Camacho more than once asking Rullán-Santiago and
Méndez-Pérez about Salinas-Acevedo, and encouraging them to get
Salinas-Acevedo involved in the drug deals.

Viewing the evidence

in the light most favorable to Salinas-Acevedo, a jury could
conclude that Camacho targeted Salinas-Acevedo and used at least

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Rullán-Santiago,

if

not

Page: 27

both

Date Filed: 01/13/2017

middlemen,8

to

induce

Entry ID: 6062247

him

to

participate in the March 24 transaction.
In

order

to

meet

the

third

requirement,

however,

Salinas-Acevedo must show that the government (via its agent
Camacho)

encouraged

Rullán-Santiago

"improper" inducement.9

Id.

to

employ

a

specific

The key issue here is whether a

specified improper inducement by Rullán-Santiago (or Méndez-Pérez)
can be attributed to the government itself.

The government would

be responsible for any improper inducement by either middleman if

8

It appears Méndez-Pérez may not have attempted to recruit
Salinas-Acevedo. The video recording from the March 24 drug deal
shows Camacho asking Salinas-Acevedo if he knows anyone
"trustworthy" that he would recommend for future deals, to which
Salinas-Acevedo suggests his "buddy" Méndez-Pérez, and then
appears surprised to hear that Méndez-Pérez was "already part of
the clan." The government argues that if Méndez-Pérez had actually
induced Salinas-Acevedo into participating in the March 24 drug
deal, Salinas-Acevedo would not have been surprised to hear he was
already in on the conspiracy. Salinas-Acevedo does not challenge
this argument.
9

Salinas-Acevedo appears to raise an alternative argument in
his reply brief that he was not required to meet this third factor
at all, and that the factors laid out in Luisi, 482 F.3d at 55,
are merely factors for the district court to weigh in assessing a
defendant's derivative entrapment theory. We need not address an
argument raised for the first time in a party's reply brief. See
N. Am. Specialty Ins. Co. v. Lapalme, 258 F.3d 35, 45 (1st Cir.
2001) ("[A]bsent exceptional circumstances, an appellant cannot
raise an argument for the first time in a reply brief."). Nor
would it make any difference here because Salinas-Acevedo is
incorrect. All five Luisi factors must be met in order to warrant
an entrapment instruction based on the conduct of a middleman.
See Luisi, 482 F.3d at 55; see also United States v. NavedoRamirez, 781 F.3d 563, 570 n.1 (1st Cir. 2015) (describing the
Luisi factors as "conditions" that must be "satisfied").

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its agent (Camacho) had "told" or "instructed" the middleman
(Rullán-Santiago or Méndez-Pérez) to apply the inducement later
deemed improper.

See United States v. Rogers, 102 F.3d 641, 645

(1st Cir. 1996) ("Under the case law the government would be
responsible if [its agent] told [the middleman] to apply the
pressure or inducement later deemed improper, and perhaps if [the
government's

agent]

knowingly

tolerated

it,

but

not

if

[the

government's agent] were ignorant of it."); Luisi, 482 F.3d at 55.
For

example,

in

Rogers,

a

government

agent

was

introduced to a third-party middleman who engaged the defendant in
a conspiracy to purchase drugs with the intent to sell.

The

defendant argued that the middleman should be treated as an
"unwitting government agent."
disagreed,

finding

that

Rogers, 102 F.3d at 645.

there

was

insufficient

We

evidence

associating the government's agent with any improper inducement by
the middleman.

Id.

We specifically noted that even if the

middleman did act improperly, nothing in the record demonstrated
that the government agent "urged, suggested, or was even aware of"
the improper conduct referenced by the defendant.
Similarly,

here,

the

record

negates

Id.
a

finding

of

improper inducement by the government itself (via its agent,
Camacho).

On multiple occasions, Camacho told his intermediaries

not to pressure Salinas-Acevedo to participate in the drug deals.
While Camacho repeatedly asked the middlemen to check on Salinas-

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Acevedo's availability and willingness to participate, there is no
evidence that he urged them to apply improper pressure on SalinasAcevedo

to

specifically

join

the

directed

enterprise.
Méndez-Pérez

To

the

that

contrary,

"if

Camacho

[Salinas-Acevedo]

gives you a lot of crap[;] . . . [t]his isn't compulsory, this is
for those who want to and know what it is."
And although Camacho did direct Rullán-Santiago to get
Salinas-Acevedo ("that guy that you tried to find last time") to
participate and Rullán-Santiago responded that he would see "if
that dog is around here," Camacho never insisted that RullánSantiago

do

whatever

it

takes

to

get

Salinas-Acevedo

to

participate. Instead, Camacho's reply -- "don't do the same shitty
thing to me like you did last week" -- appears to be a warning
about adequate notice, given that Rullán-Santiago had backed out
of the first transaction at the last minute and Camacho wanted
Rullán-Santiago to let him know "for sure" -- one way or another
-- whether Salinas-Acevedo would participate.

Salinas-Acevedo

must show not only that Camacho, through his middlemen, gave him
the opportunity to commit the crime, but also a "plus" factor -an inducement amounting to some kind of "government overreach."
Guevara, 706 F.3d at 46.

Even if we were to assume that actions

of the middlemen here were improper, Salinas-Acevedo has failed to

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produce

Document: 00117105534

sufficient

Page: 30

evidence

of

Date Filed: 01/13/2017

government

overreach

Entry ID: 6062247

or

arm-

twisting in this case.10
Salinas-Acevedo has thus failed to meet the improper
inducement prong of his two-prong burden, and we need not proceed
to the second question of whether he was already predisposed to
commit the crime.

The district court did not err in denying

Salinas-Acevedo an opportunity to present an entrapment defense.
III. SANTIAGO-CORDERO
The

last

of

the

three

defendants

in

this

appeal,

Santiago-Cordero, participated in an Operation Guard Shack drug
deal on July 8, 2010, and was tried for one count each of conspiracy

10

We do not consider Salinas-Acevedo's originally-proffered
claim that Rullán-Santiago duped him into participating in the
March 24 deal by misrepresenting it as a legitimate business
transaction over the sale of diamonds. Salinas-Acevedo conceded
below that he had no proof that it was Camacho who directed or in
any way encouraged Rullán-Santiago to tell him this lie.
See
United States v. Gates, 709 F.3d 58, 63 (1st Cir. 2013) ("[A] party
cannot concede an issue in the district court and later, on appeal,
attempt to repudiate that concession and resurrect the issue. To
hold otherwise would be to allow a litigant to lead a trial court
down a primrose path and later, on appeal, profit from the invited
error."). Because Salinas-Acevedo has no evidence connecting the
purported misrepresentation to a government agent, it does not
factor into our derivative entrapment analysis.
Although Salinas-Acevedo was not permitted to argue that he
was lied to as part of an entrapment defense, we note that he did
have an opportunity to do so at trial as part of his argument that
he lacked the mens rea to commit the crime. The jury was thus
presented evidence of the alleged misrepresentation -- including
the phone conversation in which Rullán-Santiago told Camacho that
Salinas-Acevedo would "jump off the balcony" upon seeing the drugs
-- and had the opportunity to consider it in coming to its verdict.

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to

Document: 00117105534

distribute

and

Page: 31

attempted

Date Filed: 01/13/2017

possession

with

the

Entry ID: 6062247

intent

to

distribute more than 5 kilograms of cocaine, as well as possession
of a firearm in furtherance of a drug crime.

The jury found

Santiago-Cordero guilty of the conspiracy and firearm counts, but
did not reach a verdict as to the attempted possession count.

For

his crimes, Santiago-Cordero was sentenced to 15-years and 1-month
imprisonment.
Santiago-Cordero raises two issues on appeal.
like

Salinas-Acevedo,

he

appeals

the

district

court's

denying him a jury instruction on an entrapment defense.

First,
ruling
Second,

he appeals the district court's denial of his motion for acquittal.
We start again with what happened below.
A.

Background
This has, by now, become a familiar scene with a familiar

cast of characters, so we will do our best to keep our narration
short.

Camacho and Rullán-Santiago reprise the same roles here

that they played in Salinas-Acevedo's story, as confidential FBI
informant

and

unsuspecting

middleman

turned

co-defendant,

respectively.
As he had done with Salinas-Acevedo, Rullán-Santiago
(with

Camacho's

blessing)

recruited

Operation Guard Shack drug deal.

Santiago-Cordero

for

an

Camacho was apparently aware in

the lead-up to the deal that Santiago-Cordero was money-strapped,
because during the phone calls in which they discussed bringing

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Santiago-Cordero

on

Page: 32

board,

Date Filed: 01/13/2017

Rullán-Santiago

told

Entry ID: 6062247

Camacho

that

Santiago-Cordero was in need of money.
On July 8, 2010, as planned, Santiago-Cordero arrived
with firearm in tow at the apartment where the sham drug deal would
take place.

Unaware that he was being surveilled by the FBI,

Santiago-Cordero provided security services at the deal, where
undercover officers posing as drug dealers exchanged sham cocaine
bricks for large amounts of cash.
Santiago-Cordero was paid $2,000.
Santiago-Cordero

was

After the deal was completed,
This was all caught on film.
arrested

shortly

thereafter,

charged, and stood trial along with Rivera-Ruperto and SalinasAcevedo.

During trial, the prosecution introduced testimony from

Camacho, as well as the video footage of the deal.
Toward
conference.

trial's

end,

the

court

held

a

jury

charge

There, counsel for Santiago-Cordero requested that

the jury be instructed on an entrapment defense, which the judge
denied.

After deliberations, the jury found Santiago-Cordero

guilty of the conspiracy and firearm counts, but did not reach a
verdict as to the attempted possession count.
About

a

week

after

trial,

Santiago-Cordero

filed

a

motion for acquittal, in which he argued that his conviction should
be vacated because the evidence had been insufficient to support
the jury's verdict on the conspiracy count.

The judge denied the

motion,

sentenced

and,

after

a

sentencing

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hearing,

Santiago-

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Cordero to 15-years and 1-month imprisonment.
now

appeals

both

the

sufficiency

of

the

Entry ID: 6062247

Santiago-Cordero

evidence

and

jury

instruction issues.
B.

Analysis
1.

Sufficiency of the Evidence

Santiago-Cordero argues, as he did in his motion for
acquittal below, that both his convictions should be overturned
because: (1) the government presented inadequate evidence at trial
to

support

a

guilty

verdict

on

the

conspiracy

charge,

and

(2) without the conspiracy conviction, there was no "drug crime"
on which his conviction for possession of a firearm in furtherance
of a drug crime could be based. Because Santiago-Cordero preserved
his sufficiency of the evidence argument, we apply de novo review.
See United States v. Adorno-Molina, 774 F.3d 116, 121 (1st Cir.
2014).
In order to return a conspiracy conviction under 21
U.S.C. § 846, the government must show that: "(1) a conspiracy
existed; (2) the defendant had knowledge of the conspiracy; and
(3) the defendant knowingly and voluntarily participated in the
conspiracy."
2013).
element,

United States v. Maryea, 704 F.3d 55, 73 (1st Cir.

Here, Santiago-Cordero takes issue with the "knowledge"
arguing

that

at

trial

the

government

presented

insufficient evidence that he knew the transaction involved the
distribution of drugs.

He contends that the video footage shows

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that drugs were never explicitly discussed during the transaction,
and that he never looked inside the wrapped packages to confirm
that they, in fact, contained drugs.

He also argues that Camacho

testified at trial that he did not know what Santiago-Cordero had
been

told

about

the

transaction

by

Rullán-Santiago,

and

government never put Rullán-Santiago himself on the stand.

the

Thus,

he claims, the government's evidence was insufficient to prove
beyond a reasonable doubt that he had knowledge of the nature of
the conspiracy.
But a jury verdict will not be overturned so long as we
find that a rational factfinder could have found that the evidence
presented at trial, "together with all reasonable inferences,
viewed in the light most favorable to the government," established
each element of the offense beyond a reasonable doubt.
States v. Poulin, 631 F.3d 17, 22 (1st Cir. 2011).

United

Given this

difficult standard, defendants raising this claim are "rarely
successful," United States v. Moran, 984 F.2d 1299, 1300 (1st Cir.
1993), and Santiago-Cordero is no exception.
To sustain a conspiracy conviction under § 846, the
government "need only prove that the defendant had knowledge that
he was dealing with a controlled substance, not that he had
knowledge of the specific controlled substance."
Woods, 210 F.3d 70, 77 (1st Cir. 2000).

United States v.

Here, the government

introduced at trial video footage of Santiago-Cordero, who the

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jury knew was a trained police officer, showing up for the July 8
deal armed with his firearm and ready to provide security.
Santiago-Cordero

frisked

the

undercover

buyer

upon

arrival at the deal site, and then watched as a substance packaged
in bricks and marked with logos (in the same manner as cocaine is
usually packaged) was exchanged for cash.

See United States v.

Azubike, 564 F.3d 59, 65 (1st Cir. 2009) (explaining that where
the jury was shown evidence that "the modus operandi of the crime
was the same as that of drug transactions sadly common in this
geographic area," this "support[ed] the jury's conclusion that
defendant knew he was transporting drugs").

Santiago-Cordero was

then paid $2,000 for what amounted to less than an hour of work.
The government also presented the jury with a recorded
phone call in which Rullán-Santiago told Camacho that he had
informed Santiago-Cordero that they would be working a drug deal,
as well as footage from the July 8 deal in which Camacho asks
Santiago-Cordero,

"Rullán

already

explained

Santiago-Cordero answers in the affirmative.

it

to

you?,"

and

On this evidence, a

jury had a more than adequate basis to come to its conclusion that
Santiago-Cordero had knowledge of the nature of the conspiracy.
We thus affirm.
2.

Entrapment Defense

We turn to Santiago-Cordero's appeal of the judge's
denial of an entrapment defense instruction.

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Because he raised

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the objection below, our review is de novo.

Entry ID: 6062247

See Azubike, 564 F.3d

at 64.
Having already mapped out the doctrine of derivative
entrapment in our previous discussion of Salinas-Acevedo's appeal,
we keep our discussion of Santiago-Cordero's entrapment argument
short.

Recall that a defendant is only entitled to an entrapment

defense if he can establish the government agents improperly
induced a crime that he was not already predisposed to commit.
Sánchez-Berríos, 424 F.3d at 76-77.

Here, the only evidence that

Santiago-Cordero has produced of improper inducement is that the
government knew he was "broke and needed money," and that the
government

knew

that

its

middleman,

Rullán-Santiago,

was

a

"delinquent" and used him anyway to recruit Salinas-Acevedo.
Awareness on the part of the government of a targeted
defendant's difficult financial situation does not, without more,
constitute improper inducement.

See, e.g., United States v.

Baltas, 236 F.3d 27, 37 (1st Cir. 2001). As for Santiago-Cordero's
suggestion that using Rullán-Santiago as a middleman despite his
shady reputation somehow constituted improper inducement, this
misses the mark, too.

As we explained above, the focus in an

improper inducement inquiry is on the government's tactics for
recruiting

the

defendant.

Rullán-Santiago

may

have

been

of

disreputable character, but Santiago-Cordero has not identified
any

specific

conduct

on

Rullán-Santiago's

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part,

whether

at

Case: 13-2017

Document: 00117105534

Camacho's

behest

inducement.

or

Page: 37

otherwise,

Date Filed: 01/13/2017

that

constitutes

Entry ID: 6062247

improper

Thus, Santiago-Cordero did not meet his burden of

production on an entrapment defense, and was not entitled to an
instruction at trial.
CONCLUSION
For the reasons we have stated above, we affirm.

-Dissenting Opinion Follows-

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TORRUELLA, Circuit Judge (Dissenting in Part).

The

majority holds that, as a matter of law, repeated suggestions
cannot give rise to a defense of entrapment.
dissent.

I respectfully

The purpose of sting operations is to bring willing

perpetrators to justice, not to induce law-abiding citizens to
err.

Repeated suggestions are precisely one way to induce law-

abiding citizens to err -- especially where, as here, those lawabiding citizens are in dire financial straits.
Because the majority has already laid out the facts of
this case, I summarize only the key facts here.

Salinas-Acevedo

was in debt, had a little daughter, and another child on the way
-- his financial situation was difficult, to say the very least.
Both the government agent and the middlemen knew this.

Still,

Salinas-Acevedo showed great reluctance to become involved in any
illegal drug transaction.

The middleman had to approach Salinas-

Acevedo multiple times in order to induce him to participate in
the drug transaction. Although Salinas-Acevedo initially agreed,
he later pulled out of the transaction on account of his little
girl.

It was only after being approached by the middleman again

that Salinas-Acevedo finally gave in and reluctantly participated
in the drug transaction.

The middleman's actions were all on the

direct instructions of the government agent.

Indeed, the final

instructions of the government agent to the middleman were "Hey,

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get that guy," "find, find that guy," and, once more, "[f]ind that
guy" -- all referring to Salinas-Acevedo.
I agree with the majority that we are here faced with
derivative entrapment, and that the test for that has five prongs:
(1) a government agent specifically targeted
the defendant in order to induce him to commit
illegal conduct; (2) the agent acted through
the middleman after other government attempts
at inducing the defendant had failed; (3) the
government agent requested, encouraged, or
instructed the middleman to employ a specified
inducement, which could be found improper,
against the targeted defendant; (4) the
agent’s actions led the middleman to do what
the government sought, even if the government
did not use improper means to influence the
middleman; and (5) as a result of the
middleman’s
inducement,
the
targeted
defendant in fact engaged in the illegal
conduct.
United States v. Luisi, 482 F.3d 43, 55 (1st Cir. 2007).
I also agree with the majority that the first two prongs
of this test are satisfied -- but unlike the majority, I believe
that the third prong is satisfied as well.11
The

majority

takes

great

comfort

in

the

fact

that

"[u]nder the case law the government would be responsible if [its
agent] told [the middleman] to apply the pressure or inducement

11

Because the majority does not believe that the third prong
is satisfied here, it does not reach the fourth and fifth ones.
For the same reason, the majority also does not reach the improper
inducement prong of the entrapment analysis. On the facts of this
case, I have no difficulty finding that all these prongs have been
met.

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later deemed improper, and perhaps if [the government agent]
knowingly tolerated it, but not if [the government agent] were
ignorant of it."
Cir.

1996).

United States v. Rogers, 102 F.3d 641, 645 (1st

The

majority

then

reasons

that

there

are

no

indications that the government agent engaged in any improper
inducement; the majority emphasizes that even if the middleman
somehow did engage in improper inducement, then there is no
indication that the government agent had told the middleman to do
so.
However, "examples of improper 'inducement'" include the
use of "'repeated suggestions' which succeeded only when the
defendant had lost his job and needed money for his family's food
and rent."

United States v. Gendron, 18 F.3d 955, 961 (1st Cir.

1994)(Breyer, C.J.)(quoting United States v. Kessee, 992 F.2d
1001, 1003 (9th Cir. 1993)).

In the present case, the government

agent told the middleman to engage in exactly this kind of improper
inducement, for the government agent told the middleman to approach
Salinas-Acevedo repeatedly about the drug transaction, knowing
full well that Salinas-Acevedo had serious difficulties providing
for his family, and that he had declined to participate numerous
times.12

12

Another example of improper inducement is "dogged
insistence until [defendant] capitulated". Gendron, 18 F.3d at
961 (quoting United States v. Rodriquez, 858 F.2d 809, 815 (1st
Cir. 1988)(alteration in original); see also United States v.
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Other circuits have also found that repeated suggestions
constitute

improper

inducement

for

entrapment

purposes.

See

United States v. Mayfield, 771 F.3d 417, 435 (7th Cir. 2014)(en
banc)(holding that improper inducement "may be repeated attempts
at persuasion"); United States v. Kessee, 992 F.2d 1001, 1004 (9th
Cir. 1993)("[The government agent] induced [the defendant] to sell
narcotics by repeated entreaties, which only became successful
when [the defendant] had lost both his jobs and desperately needed
the money . . . A jury could have had a reasonable doubt as to
inducement or lack of predisposition"); United States v. Burkley,
591 F.2d 903, 915 (D.C. Cir. 1978) ("[T]he trial judge correctly
issued

an

entrapment

instruction

because

(1)

[the

government

agent]'s repeated requests constituted sufficient evidence of
inducement").
It is not surprising that our sister circuits have come
out this way, because the Supreme Court has found entrapment (even
as a matter of law) where repeated suggestions were involved.
Retracing the Supreme Court's key entrapment
cases may help illuminate the problem . . .
Montoya, No. 15-2089, 2016 WL 7336577, at *2 (1st Cir. Dec. 19,
2016) ("[Improper inducement] might include, for example, . . .
relentless insistence . . . to participate in a criminal scheme).
In the present case, I have no difficulty finding that the
government agent told the middleman to engage in "dogged
insistence" or "relentless insistence." This dissent focuses on
"repeated suggestions" in light of defendant's difficult financial
situation, because the facts of this case shout out "repeated
suggestions" even more loudly than they do "dogged insistence" and
"persistent insistence."

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In Sorrells the Court found that an entrapment
instruction
was
warranted
.
.
.
the
informant's persistent appeal to military
camaraderie
qualified
as
a
potentially
entrapping inducement.
[Sorrells v. United
States, 287 U.S. 435, 441 (1932).] In Sherman
the Court found entrapment as a matter of law
. . . the inducement there consisted of
repeated requests from an informant posing as
a fellow recovering addict who had fallen off
the wagon.
[Sherman v. United States, 356
U.S. 369, 371 (1958).] In Jacobson the Court
found entrapment as a matter of law . . . the
inducement in that case was a two-year
campaign
of
fake
mail-order
entreaties
conditioning the defendant to believe that
child porn was acceptable and encouraging him
to purchase it. [Jacobson v. United States,
503 U.S. 540, 546–47 (1992).]
. . . [In each of these cases] [t]he entrapment
defense was available because the government's
solicitation of the crime was accompanied by
subtle and persistent artifices and devices
that created a risk that an otherwise lawabiding person would take the bait.
Mayfield, 771 F.3d at 434 (emphasis added).
In sting operations, the Government should know when to
take "no" for an answer, lest, as here, the "Government's quest
for conviction leads to the apprehension of an otherwise lawabiding citizen who, if left to his own devices, likely would have
never run afoul of the law." Gendron, 18 F.3d at 961 (quoting
Jacobson, 503 U.S. at 553-54)(emphasis added in original).
I respectfully dissent.

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