US v. Marin-Echeverri

Filing

OPINION issued by William J. Kayatta, Jr., Appellate Judge; Bruce M. Selya, Appellate Judge and David J. Barron, Appellate Judge. Published. [15-2187]

Case: 15-2187

Document: 00117110108

Page: 1

Date Filed: 01/25/2017

Entry ID: 6064995

United States Court of Appeals
For the First Circuit
No. 15-2187
UNITED STATES OF AMERICA,
Appellee,
v.
HERNANDO MARÍN-ECHEVERRI,
Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF PUERTO RICO
[Hon. Aida M. Delgado-Colón, U.S. District Judge]

Before
Kayatta, Selya, and Barron,
Circuit Judges.

Victoria M. Bonilla-Argudo on brief for appellant.
Rosa Emilia Rodríguez-Vélez, United States Attorney, Mariana
E. Bauzá-Almonte, Assistant United States Attorney, Chief,
Appellate Division, and Juan Carlos Reyes-Ramos, Assistant United
States Attorney, on brief for appellee.

January 25, 2017

Case: 15-2187

Document: 00117110108

Page: 2

KAYATTA, Circuit Judge.

Date Filed: 01/25/2017

Entry ID: 6064995

The defendant, Hernando Marín-

Echeverri, pled guilty to violating 21 U.S.C. §§ 952(a) and 963
and 18 U.S.C. § 1956(a)(1)(B)(i) and 1956(h), by participating in
a conspiracy to import one or more kilograms of heroin1 into the
United States and to launder the proceeds of that activity.
district court sentenced Marín to 262 months in prison.

The
Marín

appeals, arguing that the government violated the plea agreement
during

the

sentencing

hearing

and

that

constitutionally ineffective assistance of counsel.

he

received

We affirm the

sentence and dismiss the ineffective assistance of counsel claim
without prejudice to its reassertion in a collateral proceeding.
I.

Background

This appeal does not turn on the details of the crime,
so we only briefly sketch the facts, drawing from "the uncontested
portions of the change-of-plea colloquy, presentence report, and
sentencing hearing."
(1st Cir. 2016).

United States v. Gall, 829 F.3d 64, 67 n.1

We set out the procedural background at greater

length because it is central to Marín's arguments on appeal.
Between August 2012 and April 2013, Marín participated
in a conspiracy to import between ten and thirty kilograms of
heroin

into

Puerto

Rico.

Members

1

of

the

conspiracy

packed

In 21 U.S.C. § 952, an amount of "heroin" means that amount
of "a mixture or substance containing a detectable amount of
heroin." 21 U.S.C. § 960(a)(1), (b)(1)(A).

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Document: 00117110108

suitcases

full

of

heroin

Page: 3

in

Date Filed: 01/25/2017

Colombia

suitcases to couriers in Venezuela.
suitcases into the United States.

and

Entry ID: 6064995

transported

those

The couriers brought those

Members of the conspiracy also

sent heroin to Puerto Rico via the U.S. Postal Service.

Sometimes

they physically transported the proceeds from the sale of the drugs
from Puerto Rico back to Venezuela and Colombia, and sometimes
they sent the proceeds via wire transfers.

They disguised the

nature of these transfers by sending and receiving the proceeds
using the names of individuals who were not part of the conspiracy.
A grand jury returned a three-count indictment against
Marín, charging conspiracy to possess one kilogram or more of
heroin with intent to distribute, in violation of 21 U.S.C.
§§ 841(a)(1), 841(b)(1)(A)(i), and 846 (count I), conspiracy to
import one kilogram or more of heroin into the United States, in
violation of 21 U.S.C. §§ 952(a) and 963 (count II), and conspiracy
to launder the proceeds of these controlled substance offenses, in
violation of 18 U.S.C. § 1956(a)(1)(B)(i) and 1956(h) (count III).
Marín

agreed

to

plead

guilty

to

counts

government agreed to dismiss count I.

II

and

III

and

the

The resulting written plea

agreement contains two sections germane to this appeal.
Section
Calculations,"

7,

explains

captioned
that

because

"Sentencing
the

sentencing

Guidelines
court

is

required to consider the guidelines sentencing range, "the United
States and the defendant submit the following advisory Sentencing

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Document: 00117110108

Guidelines

calculations

as

Page: 4

to

Date Filed: 01/25/2017

COUNTS

TWO

and

THREE

Entry ID: 6064995

of

the

Indictment," directing the reader to "U.S. Sentencing Commission
Worksheets A, B and D attached to the instant Plea Agreement."
Those worksheets calculate Marín's total offense level to be
thirty-four.

The worksheets report the guidelines sentencing

range as 151 to 188 months because, as the plea agreement explains,
"[t]he

sentencing

guideline

calculation

contained

[in

the

worksheets] is assuming a criminal history category I but there is
no stipulation as to the defendant's criminal history category."2
Section 8, captioned "Sentence Recommendation," states
that "[t]he parties agree and recommend that the Court sentence
the defendant to a term of imprisonment at the lower end of the
applicable guideline range determined by the Court."
At Marín's change-of-plea hearing, both the Assistant
U.S.

Attorney

(AUSA)

and

the

magistrate

guidelines calculation in the worksheets.

judge

mentioned

the

After submitting the

worksheets to the court and explaining how they reached a total
offense level of thirty-four, the AUSA confirmed that "[t]he
recommendation in this case . . . would be that the defendant will
serve a term of imprisonment at the lower end of the applicable
guideline

range

determined

by

the

2

Court,

depending

on

the

Section 9 of the plea agreement repeats that the parties
have not agreed to a stipulation as to Marín's criminal history
category.

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defendant's criminal history category."

Entry ID: 6064995

The magistrate judge

later made sure Marín understood that "[i]n determining your
sentence, the presiding judge will consider but may not follow the
guidelines calculations, those calculations contained in your
agreement in those worksheets. . . . [T]hese guidelines are of an
advisory nature . . . and the presiding judge may follow or may
not follow them . . . ."
The presentence report (PSR) filed after the change-ofplea hearing but prior to the sentencing hearing placed Marín in
criminal history category III.

At the same time, it disagreed

with

calculation

the

total

offense

level

submitted with the plea agreement.

in

the

worksheets

The PSR instead calculated the

total offense level as thirty-seven.
The disagreement between the worksheets and the PSR as
to the total offense level derives from a difference in the
calculation of the adjusted offense level for the money laundering
count.

Both documents concluded that the total offense level for

the two crimes together would be equal to the higher of the two
adjusted offense levels, reduced by three levels for acceptance of
responsibility.3

The parties' worksheets calculated the adjusted

3

The PSR reached this conclusion by grouping the two counts
together under U.S.S.G. § 3D1.2(c) and applying U.S.S.G.
§ 3D1.3(a). The worksheets reached this conclusion by treating
each count as a separate group but assigning zero units to
count III under U.S.S.G. § 3D1.4(c) based on their calculation of
the offense level for that count.

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offense level for the conspiracy to import count to be thirtyseven, the sum of a base offense level of thirty-four and a threelevel upward adjustment for playing a managerial role in the
offense under U.S.S.G. § 3B1.1(b).

They calculated the adjusted

offense level for the money laundering count to be twenty-two by
applying U.S.S.G. § 2S1.1(a)(2).

The PSR, by contrast, calculated

the adjusted offense level for money laundering to be forty by
applying U.S.S.G. § 2S1.1(a)(1).

Section 2S1.1(a)(1) produced a

base offense level of thirty-four, which was enhanced by four
levels for playing a leadership role in the offense, U.S.S.G.
§

3B1.1(a),

conviction

and
was

by

two

under

levels
18

because

U.S.C.

§

the

money

1956,

per

laundering
U.S.S.G.

§ 2S1.1(b)(2)(B).
At the sentencing hearing, defense counsel challenged
the PSR calculation of the adjusted offense level for money
laundering.

She argued that the calculation in the worksheets was

correct and that the role-in-the-offense adjustment should have
been three levels for a managerial role rather than four levels
for a leadership role. The district court rejected these arguments
and adopted the calculation in the PSR.

Defense counsel did not

challenge the determination that Marín was in criminal history
category III, and the district court also adopted this conclusion
from the PSR.

A total offense level of thirty-seven and criminal

history category III yielded a guidelines sentencing range of 262

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to 327 months, rather than the range of 151 to 188 months reported
in the parties' worksheets.
After reaching this conclusion and questioning defense
counsel and the defendant further, the district court asked to
hear from the government.

The AUSA began, "The United States

abides by the sentencing recommendation contained in the plea
agreement in that the parties agreed to recommend to the Court a
sentence at the lower end of the applicable guideline range . . . ."
She then answered four questions about the facts of the case.
The district court sentenced Marín to 262 months in
prison on count II,4 which was at the low end of the guidelines
sentencing range determined by the court.

If the district court

had agreed that the total offense level was thirty-four, as
calculated on the worksheets, but still applied criminal history
category III, the guidelines sentencing range would have been 188
to 235 months.

U.S.S.G. ch. 5, pt. A (Sentencing Table).

As

mentioned above, the guidelines sentencing range reported in the
worksheets for a total offense level of thirty-four and criminal
history category I is 151 to 188 months.

4

Id.

The district court appears to have named the wrong count
when imposing the sentence. The guidelines range of 262 to 327
months was for the money laundering count, count III.
The
defendant does not raise this issue on appeal.

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II.

Date Filed: 01/25/2017

Entry ID: 6064995

Discussion

On appeal, Marín does not argue that the district court
erred in concluding that the calculations in the PSR were correct:
he was in criminal history category III and had a total offense
level of thirty-seven.

Instead, he argues that the government

breached the plea agreement.

He also argues that he received

ineffective assistance of counsel during plea negotiations.
The

government

contends

that

a

waiver-of-appeal

provision in the plea agreement bars all of Marín's arguments on
appeal other than the ineffective assistance of counsel claim.5
We sidestep the waiver issue, instead disposing of this appeal on
the merits.

See United States v. Sánchez–Maldonado, 737 F.3d 826,

827–28 (1st Cir. 2013) ("When the resolution of the underlying
appeal plainly dictates affirmance, we often have elected to avoid
the murky waters surrounding the waiver's scope and proceeded to
consider the merits of the appeal on the arguendo assumption that
the waiver does not apply.").
A.

Breach of Plea Agreement
When interpreting a plea agreement, "we construe the

terms

and

conditions

.

.

.

in

5

accordance

with

traditional

Section 10 of the plea agreement reports that "[t]he
defendant knowingly and voluntarily waives the right to appeal the
judgment and sentence in this case, provided that the defendant is
sentenced in accordance with the terms and conditions set forth in
the Sentence Recommendation provisions in this Plea Agreement."

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principles of contract law, looking outside the document only as
necessary to provide illuminating context or resolve ambiguities
in the writing."

United States v. Marchena-Silvestre, 802 F.3d

196, 202 (1st Cir. 2015) (citations omitted).
in

assessing

compliance

frown

on

technical compliance that undercuts the substance of the deal.

"A

defendant

of

who

enters

with

a

plea

a

plea

At the same time,

agreement,

agreement

waives

we

a

panoply

constitutional rights and, therefore, we hold prosecutors to 'the
most

meticulous

standards

of

both

promise

and

performance.'"

United States v. Almonte-Nuñez, 771 F.3d 84, 89 (1st Cir. 2014)
(quoting United States v. Riggs, 287 F.3d 221, 224 (1st Cir.
2002)).

"Such standards require more than lip service to, or

technical compliance with, the terms of a plea agreement."

Id.

For that reason, "it is possible for a prosecutor to undercut a
plea agreement while paying lip service to its covenants."
90–91.

"We

determining
tactics."

consider
whether

a

the

totality

prosecutor

of

the

engaged

Id. at

circumstances
in

in

impermissible

Id. at 91.
Marín ambitiously argues that the plea agreement bound

the government to advocate for a sentence within the guidelines
sentencing range calculated on the worksheets attached to the
agreement.
expressly

This argument gets nowhere because the agreement
makes

clear

that

the

worksheet

calculations

simply

"assum[e] a criminal history category I but there is no stipulation

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as to the defendant's criminal history category." Thus, the agreed
recommendation eschewed reference to the range reflected on the
worksheet, and used as its object "the lower end of the applicable
guideline range determined by the Court."
Marín drops back to arguing that the agreement at least
bound the government to recommending a sentence within a guidelines
sentencing range based on the total offense level used in the
worksheets,

allowing

movement

upward

only

calculating the criminal history category.

for

changes

in

Marín did not raise

this argument in the district court, and so we review for plain
error.

See id. at 89.

Like a judo move, this argument accepts

the force of the government's point that the agreement states that
there is no stipulation as to criminal history category and flips
it into a negative inference that there was a stipulation as to
the offense level.

In Marchena-Silvestre, we were impressed with

such an argument in the context of a plea agreement that confirmed
a

commitment

guidelines

to

recommend

range,"

a

observing

sentence
that

within

the

the

"applicable

"applicable
guidelines

range" seemed to refer to the array of alternative ranges that
were set forth in the agreement and that varied based only on
alternative possibilities for the criminal history category.
F.3d at 198, 203.
that

the

802

Here though, the plea agreement did not state

government

would

recommend

a

sentence

within

the

"applicable guidelines range," but rather within the "applicable

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guideline range determined by the Court."

Entry ID: 6064995

So while one could well

argue that an uncounseled defendant might assume that he was
exposed to an upward movement in the recommendation based only on
an upward movement in his criminal history category, we cannot
find--especially on plain error review--that a fair reading of the
agreement plainly binds the government to such an interpretation.
See Marchena-Silvestre, 802 F.3d at 204 ("[T]he second prong of
plain-error review . . . will often have some 'bite' in pleaagreement cases.

Not all breaches will be clear or obvious.

Plea

agreements are not always models of draftsmanship, so the scope of
the Government's commitments will on occasion be open to doubt."
(alteration in original) (quoting Puckett v. United States, 556
U.S. 129, 142 (2009))).
Finally, Marín's argument that the AUSA breached the
plea agreement by answering the district court's factual questions
about the crime or by not challenging the admittedly correct
guidelines calculations tendered in the PSR is foreclosed by
Almonte-Nuñez.

As we said there:

We repeatedly have emphasized that prosecutors have
a . . . solemn obligation to provide relevant information
to the sentencing court and that a plea agreement may
not abridge that obligation. . . . [T]here is a material
difference between answering questions asked by a
sentencing court or bringing facts to the court's
attention and affirmatively supporting an adjustment.
771 F.3d at 90 (citations omitted); see also United States v.
Canada, 960 F.2d 263, 270 n.7 (1st Cir. 1992) ("It is necessary at

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all times that the government 'level' with the court as to the
correct

facts

and

calculations

relevant

to

guideline

sentencing.").
B.

Ineffective Assistance of Counsel
Marín

also

contends

that

he

received

ineffective

assistance of counsel during the negotiation of the plea agreement
and at the sentencing hearing, in violation of the Sixth Amendment.
See Strickland v. Washington, 466 U.S. 668, 686 (1984); see also
Hill v. Lockhart, 474 U.S. 52, 58 (1985) (applying Strickland to
claim

of

ineffective

assistance

of

counsel

during

plea

negotiation).
"Under Strickland, we first determine whether counsel's
representation
reasonableness.'

'fell

below

an

objective

standard

of

We then inquire whether 'there is a reasonable

probability that, but for counsel's unprofessional errors, the
result of the proceeding would have been different.'"

Parsley v.

United States, 604 F.3d 667, 671 (1st Cir. 2010) (citations
omitted).

"With regard to plea agreements, counsel has a critical

obligation . . . to advise the client of the advantages and
disadvantages of a plea agreement."

Id. (alteration in original)

(citations omitted).
Marín argues that he received ineffective assistance of
counsel because his attorney negotiated his plea agreement, and
made recommendations as to whether he should accept or reject that

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understanding

the

relevant

Entry ID: 6064995

agreement,

without

sentencing

guidelines.

This misunderstanding persisted, he claims, even when

she was objecting to the PSR and arguing at the sentencing hearing.
In

Marín's

view,

the

arguments

that

his

attorney

advanced in the objection to the PSR and at sentencing make clear
that she did not understand the guidelines.

Her arguments assumed

that the difference in total offense level between the worksheets
and the PSR arose from the application of the offense grouping
guideline

and

§ 2S1.1(b)(2)(B).

the

two-level

enhancement

under

U.S.S.G.

Neither the objection nor the argument at the

sentencing hearing so much as mentioned the distinction between
U.S.S.G. § 2S1.1(a)(1) and (a)(2).

Even after the district court

explained at the sentencing hearing that the PSR calculated the
adjusted

offense

level

for

money

laundering

using

U.S.S.G.

§ 2S1.1(a)(1), defense counsel continued to press an argument based
on grouping.
Nevertheless,

we

decline

Marín's

request

that

we

evaluate his ineffective assistance claim on this appeal. "As a
general rule, this court does not review ineffective assistance of
counsel claims on direct appeal."

United States v. Vázquez-

Larrauri, 778 F.3d 276, 293 (1st Cir. 2015).

This general rule

results from the fact that such claims are usually not raised in
the original district court proceedings in which the defendant is
represented by the lawyer said to be ineffective, and therefore

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the record is usually insufficient for meaningful review.
293-94.

We see no reason to make an exception here.

not yet raised the claim in the district court.
otherwise

a

situation

in

which

"the

critical

Id. at

Marín has

Nor is this
facts

are

not

genuinely in dispute and the record is sufficiently developed to
allow reasoned consideration of an ineffective assistance claim."
United States v. Natanel, 938 F.2d 302, 309 (1st Cir. 1991).

To

the contrary, "why counsel acted as [s]he did" is undeveloped,
Vázquez-Larrauri, 778 F.3d at 294 (citation omitted), and the
record does not rule out the possibility that defense counsel
noticed the potential problem in the calculation of the total
offense

level

negotiations

for

and

the

chose

money
not

to

laundering
bring

it

count
to

the

during

plea

government's

attention in the hope that it would go unnoticed, to the benefit
of her client.

Thus, we dismiss the ineffective assistance claim

without prejudice to its reassertion, if the defendant so chooses,
in a collateral proceeding under 28 U.S.C. § 2255.

See United

States v. Cardoza, 790 F.3d 247, 248 (1st Cir. 2015) (per curiam).
We do think that the form of plea agreement used in this
case created a nontrivial risk that the defendant would misread it
unless well counseled.

A pleading defendant is usually most

interested in two things concerning the meaning of a plea agreement
under Federal Rule of Criminal Procedure 11(c)(1)(B):

the length

of the sentences in the guidelines sentencing range and the

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recommendation that the government will make.

Entry ID: 6064995

While we agree, as

explained above, that a lawyerly reading of the agreement reveals
that all it really says is that the government will recommend the
low end of the range as determined by the court, whatever that may
be, a lay person could easily look at this plea agreement and
assume that it says something more.
the

worksheets

After all, why bother with

otherwise--especially

since

they

grossly

underestimated the range, provided no examples of the higher ranges
possible, and might have been read as implying that criminal
history was the only variable?

With such an agreement, the

government may well risk its ability to sustain the voluntariness
of the plea should the evidence support a claim that defense
counsel did not explain the bait-and-switch potential.
III.

Conclusion

For the forgoing reasons, we affirm Marín's sentence and
dismiss

his

ineffective

assistance

prejudice.

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of

counsel

claim

without