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


                                       - 3 -
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.


                                        - 4 -
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.


                                      - 5 -
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


                                      - 6 -
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."


                                           - 8 -
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


                                         - 9 -
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


                                    - 10 -
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


                                      - 13 -
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


                                       - 14 -
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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