United States v. Marin-Echeverri , 846 F.3d 473 ( 2017 )

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
KAYATTA, Circuit Judge. 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. The
district court sentenced Marín to 262 months in prison. Marín
appeals, arguing that the government violated the plea agreement
during the sentencing hearing and that he received
constitutionally ineffective assistance of counsel. 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." United States v. Gall, 829 F.3d 64, 67 n.1
(1st Cir. 2016). 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 of the conspiracy packed
1 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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suitcases full of heroin in Colombia and transported those
suitcases to couriers in Venezuela. The couriers brought those
suitcases into the United States. 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 II and III and the
government agreed to dismiss count I. The resulting written plea
agreement contains two sections germane to this appeal.
Section 7, captioned "Sentencing Guidelines
Calculations," explains that because the sentencing court is
required to consider the guidelines sentencing range, "the United
States and the defendant submit the following advisory Sentencing
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Guidelines calculations as to COUNTS TWO and THREE 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 judge mentioned the
guidelines calculation in the worksheets. 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 Court, depending on the
2
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." 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-of-
plea hearing but prior to the sentencing hearing placed Marín in
criminal history category III. At the same time, it disagreed
with the total offense level calculation in the worksheets
submitted with the plea agreement. 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 thirty-
seven, the sum of a base offense level of thirty-four and a three-
level 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), and by two levels because the money laundering
conviction was under 18 U.S.C. § 1956, per 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. Id.
4 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. 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 accordance with traditional
5
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). At the same time,
in assessing compliance with a plea agreement, we frown on
technical compliance that undercuts the substance of the deal. "A
defendant who enters a plea agreement waives a panoply of
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." Id. at
90–91. "We consider the totality of the circumstances in
determining whether a prosecutor engaged in impermissible
tactics." 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. This argument gets nowhere because the agreement
expressly 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 for changes in
calculating the criminal history category. 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 to recommend a sentence within the "applicable
guidelines range," observing that the "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. 802
F.3d at 198, 203. Here though, the plea agreement did not state
that the 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." 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 plea-
agreement 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 'fell below an objective standard of
reasonableness.' 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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agreement, without understanding the relevant 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 the two-level enhancement under U.S.S.G.
§ 2S1.1(b)(2)(B). 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. Id. at
293-94. We see no reason to make an exception here. Marín has
not yet raised the claim in the district court. Nor is this
otherwise a situation in which "the critical 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 for the money laundering count during plea
negotiations and chose not to bring it to the 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. 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. After all, why bother with
the worksheets 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 of counsel claim without
prejudice.
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