United States v. Cortes-Lopez

U.S. Court of Appeals for the First Circuit
United States v. Cortes-Lopez, 101 F.4th 120 (1st Cir. 2024)

United States v. Cortes-Lopez

Opinion

            United States Court of Appeals
                       For the First Circuit


No. 22-1918

                           UNITED STATES,

                              Appellee,

                                 v.

                       ALEJANDRO CORTÉS-LÓPEZ,

                        Defendant, Appellant.


            APPEAL FROM THE UNITED STATES DISTRICT COURT
                  FOR THE DISTRICT OF PUERTO RICO

           [Hon. Francisco A. Besosa, U.S. District Judge]


                               Before

                 Rikelman, Hamilton,* and Thompson,
                          Circuit Judges.


     Franco L. Pérez-Redondo, Assistant Federal Public Defender,
with whom Héctor L. Ramos-Vega, Interim Federal Public Defender,
was on brief, for appellant.

     Maarja T. Luhtaru, with whom W. Stephen Muldrow, United States
Attorney, and Mariana E. Bauzá-Almonte, Assistant United States
Attorney, were on brief, for appellee.


                            May 10, 2024




     *   Of the Seventh Circuit, sitting by designation.
          THOMPSON,   Circuit Judge.   Alejandro Cortés-López is

serving a 24-month term of imprisonment after pleading guilty to

conspiracy to commit mail and wire fraud.     In this direct appeal,

he asks this court to vacate his sentence and remand to the

district court because the government, he asserts, breached the

plea agreement during the sentencing hearing.        On plain error

review, we conclude the government did just that.      We therefore

vacate Cortés' sentence and remand for further proceedings.

                       HOW CORTÉS GOT HERE1

          In July 2020, a grand jury indicted Cortés and a co-

defendant with conspiracy to commit mail and wire fraud, one count

of securities fraud, and several substantive counts of wire fraud.

In March 2022, Cortés entered into a plea agreement with the

government, stipulating that, from 2010 to 2017, he perpetrated a

fraudulent financial scheme in which he solicited residents in

Puerto Rico to invest in short-term, high-interest loans in the

Dominican Republic through The Republic Group, Inc., a Florida

corporation.   Cortés stipulated that he used the money from the

investors to pay himself and to distribute supposed returns on

prior investments to the earlier investors -- so-called "lulling

payments" -- so the investors were further duped "into a false


     1 We draw the relevant facts presented herein from the plea
agreement, the undisputed parts of the presentence investigation
report, and the sentencing transcript.     See United States v.
Ubiles-Rosario, 
867 F.3d 277
, 280 n.2 (1st Cir. 2017).


                              - 2 -
sense of security that their investments were safe and performing

as promised."       Cortés copped to his actions, agreeing to plead

guilty to conspiracy to commit mail and wire fraud.

            In the plea agreement, the parties agreed that the

sentencing guidelines calculation would lead to a total offense

level (TOL) of 18.        Important for the discussion to come, the

agreement's   TOL    contemplated    a    14-level    enhancement       for   the

agreed-to   $749,200     loss   amount,   which,     when    combined    with   a

criminal history category of I (Cortés had no prior arrests or

convictions), would suggest a guidelines sentencing range (GSR) of

27-33 months' imprisonment.        Nonetheless, the parties promised to

jointly   request    a   variant   sentence   of     24     months'   probation

regardless of the court's final TOL calculation.              In addition, the

government agreed to move to dismiss the other counts in the

indictment still pending at the time of sentencing.              For his part,

Cortés waived his right to appeal the sentence if the sentence

imposed by the district court was within or below the sentence

recommendation agreed to by the parties.                  The district court

accepted Cortés' change of plea in April.

            According to the Presentence Investigation Report (PSR),

Cortés' and his co-defendant's financial fraud scheme resulted in

more than $5.4 million in losses to the investors.              The probation

office therefore applied an 18-level addition to the base offense

level (applicable when the loss exceeds $3.5 million), as well as


                                    - 3 -
a 6-level enhancement for substantial financial hardship to 25 or

more victims.2       Prior to the sentencing hearing, Cortés filed a

written objection to these enhancements as not in line with the

figures to which the parties had stipulated in the plea agreement.

The   probation      office    responded   with    an   addendum    to   the    PSR

explaining how it arrived at the precise levels applied and noting

that, based on information provided by the Assistant U.S. Attorney

about the number of victims identified from the scheme, the higher

loss amount and inclusion of the additional enhancement were

"correct."

             At   Cortés'      November    2022    sentencing      hearing,     his

attorney told the court that 24 months' probation was a just

sentence because this was Cortés' first offense, he accepted

responsibility for his role in the scheme and, pursuant to an

agreement     with    the     Securities   and    Exchange   Commission       (SEC)

resulting from the prosecution of the same fraud scheme in the

Southern District of Florida, he had been working and paying

restitution even before the grand jury indicted him in this case.3

The government's response was, in its entirety:


      2 These
            proposed enhancements meant a TOL of 28 which, when
combined with a criminal history category of I, provided a GSR of
78-97 months.

      3   In the plea agreement, Cortés
      agree[d] to the entry of an order of restitution in the
      amount of $749,200 jointly and severa[l]ly with the co-
      defendant, through the payment plan established pursuant


                                      - 4 -
     Your Honor, we will be very brief, but before we make
     our argument, I would like to highlight the fact that
     the defendant filed some objections to the [PSR], and
     Probation responded to those objections by Defendant,
     and the United States believes the United States
     Probation Office is correct in their assessment of those
     enhancements.   Nonetheless, the United States and the
     defendant entered into a plea agreement wherein the
     United States and the defendant took into consideration
     a specific amount of loss.

     So for that reason, the United States is standing by its
     plea agreement recommendation of 24 months of probation
     in this case for this defendant, together with a judgment
     for restitution in the amount of . . . $749,200 that the
     defendant should pay jointly and severally with the co-
     defendant in this case. The defendant should do this
     pursuant to the payment plan established already in the
     case before the [SEC], and that case number is 20-CV-
     23616-DPG. That would be all from our part.

The district court summarily denied Cortés' objections to the PSR

after commenting "that the probation officer is free to consider

everything, not just what's in the plea agreement."   The Assistant

U.S. Attorney then added that she "wanted to remind the Court that

we have two victims present who would like to speak."    After the

two victims spoke, Cortés allocuted at some length, apologizing to

his family, acknowledging responsibility for his actions, and

pledging an intent to spend the rest of his life repairing the

financial harm he caused to the victims of the scheme.




     to the judgment entered against the defendant in case
     no. 20-cv-23616-DPG on September 30, 2020 in the United
     States District Court, Southern District of Florida in
     favor of the [SEC].


                              - 5 -
            The district court assigned the same base offense level

of 7 as that reflected in the plea agreement and subtracted 3

levels for acceptance of responsibility but then added 18 levels

(rather than the plea-agreement-contemplated 14) accounting for

the $5.4 million loss amount listed in the PSR and added 6 levels

for causing substantial financial hardship to more than 25 victims.

This brought the TOL to 28 (rather than 18).                 With a criminal

history category of I, the GSR was 78-97 months.              The court said

it had considered the PSR, the plea agreement, the sentencing

memoranda filed by each side, the victims' statements, the parties'

arguments,    Cortés'   allocution,    and   the       
18 U.S.C. § 3553
(a)

factors.     The court opted to impose a sentence of incarceration,

stating that the requested sentence of probation did not reflect

the seriousness of the offense, promote respect for the law,

protect the public, or address deterrence and punishment, but

assigned a below-guidelines sentence in consideration that Cortés'

involvement was less than that of his co-defendant.                   The court

pronounced a sentence of 24 months' imprisonment to be followed by

3 years of supervised release and $5.4 million in restitution to

be paid jointly and severally with the co-defendant in accordance

with the co-defendant's judgment.        Cortés' attorney immediately

requested    reconsideration   and    proposed     a    5-year   sentence    of

probation so Cortés could continue to work and make restitution

payments.     The court summarily denied this idea.                  Before the


                                 - 6 -
hearing   ended,   Cortés'    attorney      lodged   an    objection   to   the

sentence,      labeling      it     procedurally          and   substantively

unreasonable.4

             Now before us, Cortés challenges his 24-month term of

immurement on the sole basis that the government breached the plea

agreement during the sentencing hearing by:               (1) voicing support

for the higher TOL calculated in the PSR; and (2) failing to

"advocate meaningfully" for the agreed upon 24-month probation

sentence.5

                                  DISCUSSION

             We kick off our discussion by deciding whether Cortés

forfeited his arguments by not first raising them to the district

court, a threshold point so we can pin down the applicable standard

of review for Cortés' challenge to his sentence.

             This court generally reviews a claim that the government

breached a plea agreement de novo, but the review shifts to plain


     4As promised, the government requested that the court dismiss
the indicted counts of securities fraud and wire fraud; the court
dismissed these counts.
     5  Cortés' plea agreement includes a waiver of appeal
provision, triggered "if the sentence imposed by the [c]ourt is
within or below the sentence recommendation submitted by the
parties." Waiver provisions such as this one foreclose only the
"appeals that fall within its scope." United States v. Almonte-
Nuñez, 
771 F.3d 84, 88
 (1st Cir. 2014). As Cortés points out, and
the government agrees, this waiver clause does not preclude his
appeal because the district court sentenced him to a term of
imprisonment and not to a term of probation -- the sentence
therefore falls outside the scope of that contemplated by the
agreement.


                                    - 7 -
error when a defendant had an opportunity to raise the issue to

the district court but did not and therefore, in legal lingo,

forfeited the argument.         United States v. Sierra-Jiménez, 
93 F.4th 565
, 570 (1st Cir. 2024).         Cortés admits that he did not raise the

breach-of-the-agreement         issue    to     the   district         court,   but   he

attempts    to   salvage    our   plenary       review     by    arguing    that      any

objection he might have raised at the sentencing hearing was

futile.      According     to   him,    this     judge     has    an    "unflinching,

unyielding position that government promises begin and end with

the rote recitation of a number of months," meaning as long as the

government mouths, on sentencing day, the agreed-upon months and

nothing more, then its obligation to the bargain is fulfilled.

Just look, says Cortés, at two other appeals pending before this

court wherein the defendants alerted the district court in writing

to   the   government's    alleged      breaches      of    the    respective      plea

agreements during the lead up to the sentencing hearing, but the

district court denied their plaints.6                 And in any event, Cortés

continues, this court has excused "[a] party's failure to spell

out a claim in the district court . . . if he had no reasonable

opportunity to do so," United States v. Fernández-Garay, 788 F.3d



      6In those two cases, the respective defendants argued that
the government, in its sentencing memoranda, included content and
arguments intended to sway the court to impose higher sentences
than those to which the government had agreed in the respective
plea agreements.


                                        - 8 -
1, 4 (1st Cir. 2015) (citing Fed. R. Crim. P. 51(b)), because "a

court should not require a lawyer 'to persist stubbornly when the

judge has made it perfectly clear that he does not wish to hear

what the lawyer has to say,'" 
id.
 (quoting United States v.

Toribio-Lugo, 
376 F.3d 33, 41
 (1st Cir. 2004)).        This Fernández-

Garay conundrum, implies Cortés, is the predicament in which he

found himself below.   However, we cannot agree with Cortés on this

point.   In Fernández-Garay, the court completely cut off the

attorney's   attempt   to   object   during   a   sentencing   hearing,

precluding the attorney from stating the intended objection.        
Id.

Here, by contrast, there is no indication anywhere in the record

that Cortés' counsel attempted to bring the purported breach to

the court's attention at all, either in papers leading up to

sentencing, or even when he objected at the end of the hearing to

the sentence as procedurally and substantively unreasonable.        As

the government argues, neither Fernández-Garay nor the unrelated

pending appeals get Cortés over the hurdle of this circuit's clear

precedent that alleged breaches are reviewed for plain error when

the issue is raised for the first time on appeal.         See Sierra-

Jiménez, 93 F.4th at 570; United States v. Gall, 
829 F.3d 64, 70

(1st Cir. 2016).   We will therefore review Cortés' arguments about

the government's purported breach under the plain error standard

of review, meaning "we consider whether:      (1) there was error, (2)

it was plain, (3) the error affected the defendant's substantial


                                - 9 -
rights,   and   (4)   the   error   adversely   impacted   the    fairness,

integrity, or public reputation of judicial proceedings."           Sierra-

Jiménez, 93 F.4th at 570 (quoting United States v. Rivera-Ruiz, 
43 F.4th 172
, 179 (1st Cir. 2022)).

           The applicable standard of review in place, we turn to

laying out the legal principles that govern our consideration of

purported plea agreement breaches by the government.             Out of the

gate one indisputable point is worth noting.          There is no doubt

whatsoever that plea agreements play an "important role . . . in

our criminal justice system."        United States v. Frazier, 
340 F.3d 5, 10
 (1st Cir. 2003).      As this court has long acknowledged:

     Disposition of charges after plea discussions is not
     only an essential part of the process but a highly
     desirable part for many reasons. It leads to prompt and
     largely final disposition of most criminal cases; it
     avoids much of the corrosive impact of enforced idleness
     during pretrial confinement for those who are denied
     release pending trial; it protects the public from those
     accused persons who are prone to continue criminal
     conduct even while on pretrial release; and, by
     shortening the time between charge and disposition, it
     enhances whatever may be the rehabilitative prospects of
     the guilty when they are ultimately imprisoned.

Id.
 (quoting Santobello v. New York, 
404 U.S. 257, 261
 (1971)).

In addition, plea bargaining "conserve[s]" "scarce judicial and

prosecutorial resources . . . for those cases in which there is a

substantial issue of the defendant's guilt or in which there is

substantial doubt that the [government] can sustain its burden of

proof."   Brady v. United States, 
397 U.S. 742, 752
 (1970); see



                                    - 10 -
also Stephanos Bibas, Plea Bargaining Outside the Shadow of Trial,

117 Harv. L. Rev. 2463
, 2470 (2004)                 (explaining that         "[t]he

strength of the prosecution's case is the most important factor"

influencing     the     government's        negotiations   during      the   plea-

bargaining process).        The process of plea bargaining, therefore,

"flows   from    'the    mutuality     of    advantage'    to   defendants     and

prosecutors, each with his own reasons for wanting to avoid trial."

Bordenkircher v. Hayes, 
434 U.S. 357, 363
 (1978) (quoting Brady,

397 U.S. at 752
).

           In giving structure to the plea-bargaining apparatus,

we've leaned on one primary legal theory which sounds in contract.

Thus, application of traditional contract law principles allows us

to   interpret     plea     agreements        and   evaluate     the     parties'

performances of duties thereunder.               United States v. Brown, 
31 F.4th 39
, 50 (1st Cir. 2022).        We've noted that when the government

enters into a plea agreement with a defendant, the court should

hold the government to "the most meticulous standards of both

promise and performance" because "a defendant who enters a plea

agreement waives fundamental constitutional rights."                   
Id.
 (first

quoting United States v. Marín-Echeverri, 
846 F.3d 473, 478
 (1st

Cir. 2017)).     The government, then, must serve more than simple

"lip service to, or technical compliance with, the terms of a plea

agreement," in part because the defendant is entitled to both the

"benefit of the bargain struck in the plea deal and to the good


                                     - 11 -
faith of the prosecutor."     United States v. Lessard, 
35 F.4th 37
,

42 (1st Cir. 2022) (quoting other First Circuit cases).                We've

also   underscored   the   challenge   of    our   compliance    examination

indicating that there is "no magic formula" for determining whether

a prosecutor satisfied their duty under plea agreement terms to

recommend a particular sentence.       
Id.
 (cleaned up).        Rather, this

court considers the totality of the circumstances, asking "whether

the prosecutor's 'overall conduct [is] reasonably consistent with

making [the promised] recommendation, rather than the reverse.'"

Id.
 (alterations in original) (quoting United States v. Canada,

960 F.2d 263, 269
 (1st Cir. 1992)).         In fulfilling its side of the

bargain, the government "is not obliged to present an agreed

recommendation either with ruffles and flourishes," United States

v. Montañez-Quiñones, 
911 F.3d 59, 65
 (1st Cir. 2018), or "with

any particular degree of enthusiasm," though it is improper for

them "to inject material reservations about the agreement to which

the government . . . committed," Canada, 
960 F.2d at 270
.               That

said, "we are wary of government claims that the prosecution

'technically' complied with the terms of the agreement when the

net effect of the government's behavior undermines the 'benefit of

the bargain' upon which a defendant has relied."                Frazier, 
340 F.3d at 10
. "Our case law prohibits 'not only explicit repudiation

of the government's assurances[] but must in the interests of




                                 - 12 -
fairness be read to forbid end-runs around them.'"              
Id.
 (quoting

United States v. Saxena, 
229 F.3d 1, 6
 (1st Cir. 2000)).

            While prosecutors are duty-bound to carry out both the

letter and spirit of the government's plea agreement, this court

recognizes    that   they    have   "a   concurrent     and   equally   solemn

obligation   to    provide   relevant     information    to   the   sentencing

court," United States v. Almonte-Nuñez, 
771 F.3d 84, 86, 90
 (1st

Cir. 2014), including "full and accurate information about the

offense and the offender," 
id. at 86
.             Within this concurrent

obligation "[w]e have recognized a tension between the general

principle that the government has a duty to provide to the court

reliable information relevant to sentencing and the fact that

'certain factual omissions, helpful to the defendant, may be an

implicit part of the bargain in a plea agreement.'"            United States

v. Davis, 
923 F.3d 228, 237
 (1st Cir. 2019) (alteration omitted)

(quoting United States v. Miranda-Martinez, 
790 F.3d 270, 274
 (1st

Cir. 2015)).      Overall, the prosecutor's "twin" duties to stand by

the plea agreement and provide information to the court "can

sometimes    'pull   in   different      directions,'"    United    States   v.

Ubiles-Rosario, 
867 F.3d 277, 283
 (1st Cir. 2017) (quoting United

States v. Cruz-Vázquez, 
841 F.3d 546, 549
 (1st Cir. 2016)), but

     "there is a material difference between answering
     questions asked by a sentencing court or bringing facts
     to the court's attention," on the one hand, and, on the
     other, engaging in conduct that violates the [explicit]
     terms of the plea agreement, by, for example,


                                    - 13 -
       "affirmatively   supporting   an   adjustment"  to   the
       guideline range when the plea agreement "obligate[s] the
       government to refrain from arguing further guideline
       adjustments,"

id. at 284 (second alteration in original) (quoting Almonte-Nuñez,

771 F.3d at 90
).         With these general legal principles in the

backdrop, we proceed to our review of what happened here, starting

with whether the government's conduct at the sentencing hearing

plainly breached the plea agreement.                 See United States v. Riggs,

287 F.3d 221, 225
 (1st Cir. 2002).               Cortés contends it did so in

two specific respects, but, as we've already established, we review

circumstances in their totality to determine whether any breach

occurred.     See Lessard, 35 F.4th at 42.              To that end, we present

-- and then proceed to consider -- all of Cortés' arguments

together through plain error spectacles.

            According    to     Cortés,        the     government's         unsolicited

statement    of    agreement    at     the     hearing        with    the     PSR's   TOL

calculation    (recall    it    was     10     points        higher    than    the    TOL

contemplated in the plea agreement) represented a repudiation of

the    agreement   between     the    parties        about    the     appropriate     TOL

calculation and was in fact a form of advocating for the higher

TOL.    Add to that, says Cortés, the government's sole one-sentence

request for the agreed-upon 24 months' probation cannot reasonably

be viewed as fulfilling its obligation to support the negotiated

agreement     because     the        request     immediately           followed       the



                                       - 14 -
government's acknowledgment that the plea agreement included an

inaccurate guidelines calculation.          To again bring to the gentle

reader's mind what the government said below when it set out to

fulfill its obligations under the plea bargain:

     [T]he United States believes the United States Probation
     Office is correct in their assessment of those
     enhancements.   Nonetheless, the United States and the
     defendant entered into a plea agreement wherein the
     United States and the defendant took into consideration
     a specific amount of loss.     So for that reason, the
     United States is standing by its plea agreement
     recommendation of 24 months of probation in this case
     for this defendant.

Cortés points out that the government did not even try "to explain

to the court how its view of the § 3553(a) factors shaped its

recommendation for a [TOL] of 18 [in the plea agreement], as

opposed   to   28   [in   the   PSR]."      Rather,   argues   Cortés,   its

recommendation fell "woefully short of fulfilling" its duty under

the plea agreement because "no impartial observer would perceive

the prosecutor's tepid statement as a genuine endorsement of a

probationary disposition."

           Cortés acknowledges that the government "stood by" the

recommendation for 24 months' probation and was not obligated to

"argue enthusiastically" but he asserts that the government was

required to do more than what it did.          Cortés says he "bargained

for the United States to put its reputational weight behind" the

sentencing     recommendation,    which,    according   to   him,   includes

explaining to the district court why a sentence of probation was


                                   - 15 -
warranted here rather than incarceration.     Instead, the district

court heard the prosecutor endorse the final TOL        absent any

justification as to why it had agreed to and recommended the below-

guidelines, non-incarcerative sentence.     To Cortés, this silence

signaled to the district court that the government "didn't really

believe in the agreement's recommendation."   This was an error and

a breach, argues Cortés, when viewed in light of this court's prior

discussions and holdings about claimed plea agreement breaches.

          The government, of course, sees things differently.    It

argues that it complied to a T with the terms of the agreement,

doing exactly what it promised to do, and -- responding to Cortés'

asseverations -- did not maneuver behind the scenes to raise the

TOL in the PSR, undermine the plea agreement, or advocate for the

application of a higher TOL than that memorialized in the plea

agreement.   Providing probation with the information about the

victims was part of its duty to provide accurate information to

the court, argues the government, as was noting the defendant's

pre-hearing objections to the PSR's TOL since the defendant had

failed to address those objections during his own sentencing

argument to the court.    The government also reminds us that it

recommended the lower restitution amount agreed to in the plea

agreement, was unequivocal in its recommendation for 24 months'

probation, and followed through with dismissing the remaining

counts.   The government urges us to conclude that the totality of


                              - 16 -
the   circumstances      is      therefore     distinguishable     from        those

occasions where this court has found a breach.

           When previously presented with this type of claim on

appeal,   this   court     has     examined    government     conduct     in    its

conveyance of a plea agreement and has explained when its actions

have fallen short:    The government presented the parties' sentence

recommendation but undercut it by making "grudging and apologetic"

references to the plea agreement and emphasizing the defendant's

roles in the offense before urging the court to impose a lengthy

sentence, Canada, 
960 F.2d at 269
; the government -- in its

sentencing    memorandum      --    opposed    an    agreed-to   acceptance-of-

responsibility adjustment to the guidelines calculation, United

States v. Clark, 
55 F.3d 9, 12
 (1st Cir. 1995); and the government,

despite recommending the agreed-upon sentence, argued the facts in

a way that undercut the recommendation, United States v. Gonczy,

357 F.3d 50, 54
 (1st Cir. 2004).

           Conversely, on the "no breach" side of our case law, the

government is correct that it can acknowledge the accuracy of the

GSR calculation in a PSR without breaching a plea agreement.                    See

United States v. Carbajal-Váldez, 
874 F.3d 778, 785-86
 (1st Cir.

2017).    The government may also provide "facts concerning the

background,   character,      and    conduct    of    the   defendant"    without

giving us pause. Ubiles-Rosario, 
867 F.3d at 284
 (quoting Miranda-

Martinez, 
790 F.3d at 274
).             We have further found no breach


                                     - 17 -
occurred when, despite highlighting the dangerous nature of a

defendant's conduct and his "substantial violent criminal record,"

Brown, 31 F.4th at 46, the government made statements "'early,

often,   and     throughout     the     sentencing'     hearing"       that   its

recommended sentence was based on a specific TOL, id. at 51

(quoting Ubiles-Rosario, 
867 F.3d at 286-87
); see also Rivera-

Ruiz, 43 F.4th at 180 (holding no breach when the government

repeatedly stated the agreed-to recommendation but volunteered

additional facts not included in the plea agreement in response to

the defendant's argument about why the agreed-to sentence was

warranted); Lessard, 35 F.4th at 43 (holding no breach when the

government     argued   against   the      downward    variant   sentence     the

defendant requested after complying with the terms of the agreement

and requesting a sentence at the low end of the GSR).

          All     in    all,   when   we   survey     this   court's    previous

discussions of alleged breaches a clear pattern is revealed. Under

a totality-of-the-circumstances lens, an appellant need not show

a complete out-and-out repudiation of a plea agreement before this

court will conclude the government failed to uphold its end of the

bargain. Rather, we ask "whether the prosecutor's 'overall conduct

is reasonably consistent with making the promised recommendation,

rather than the reverse,'" Lessard, 35 F.4th at 42 (cleaned up)

(quoting Canada, 
960 F.2d at 269
); see United States v. Wyatt, 
982 F.3d 1028
, 1030 (7th Cir. 2020) ("Prosecutors, who have the benefit


                                      - 18 -
of drafting plea agreements to their own satisfaction, must adhere

to their promises.").              Also, we believe the sum of our case law

reflects an elemental understanding of what we should reasonably

expect from the government at sentencing:                       "[W]hen the net effect

of   the    government's        behavior       [at    sentencing]        undermines      the

benefit     of       the   bargain    upon    which       a    defendant   has    relied,"

technical compliance with the plea agreement may not suffice to

make up for other statements and behavior that can be viewed as an

end-run around the terms of the agreement.                        Frazier, 
340 F.3d at 10
 (internal quotation marks and citation omitted).                             Putting it

all together, determining whether a breach occurred is highly

dependent on the individual circumstances of the case at bar. With

that lens in place, we can now focus on the specific circumstances

before us in Cortés' sentencing experience, explaining why we agree

with him that the government's overall conduct here was, in fact,

a breach of the plea agreement.

                As    Cortés   argues,       the   government         bargained    for   and

promised to recommend a sentence based on a TOL which considered

$749,200 as the loss amount.                 But its statements at the hearing

imply      it   changed      its     mind    at    some       point   between     providing

information about the victims to the probation office and the

hearing.7 At the sentencing hearing, the government did not simply


      7Although Cortés hopes we perceive the government's action
of providing the probation office with the raw information about


                                            - 19 -
give a nod to the accuracy of probation's guidelines calculations.

It announced that the PSR and not the plea agreement reflected the

"correct"    loss     amount,    thereby      completely    undermining   the

previously    bargained-for      and    promised    numbers.      While   the

government says it was simply offering information to the court to

complete     the    picture     of   the      pre-hearing   objections    and

resolutions, when viewed in context, we cannot agree.

            Indeed,    the    cold     sentencing   transcript    shows   the

dynamics that were in play at the proceeding.               The first words

spoken by the prosecutor after the defense finished its sentencing

argument were not ones that placed before the court the substance

of the parties' plea agreement but were, instead, utterances to

"highlight" the objections to the PSR lodged by the defendant to

which the probation office had responded by providing supportable

justifications for the increased, additional enhancements.                The

prosecutor then, sua sponte and without elaboration, indicated her

agreement with the PSR's calculation before ultimately stating

that the parties had entered into a plea agreement with a different

loss amount in mind and so the government would "stand by" the



the victims of Cortés' scheme (from which probation decided the 6-
level enhancement for substantial financial hardship to 25+
victims applied) as further evidence of the government's breach,
this action squarely falls into the category of the government's
"solemn obligation" to provide the district court with accurate
information about the case, starting with responding accurately to
the probation office's requests for information.      See Ubiles-
Rosario, 
867 F.3d at 283
.


                                     - 20 -
recommendation in the agreement for the sentence and restitution

figures reflected therein.           And that (other than reminding the

court that two victims were present to make statements on the

record) was the sum total of what the prosecutor chose to offer

about the plea deal prior to the district court imposing sentence.

            To be clear, in finding fault, as we do, with the

government's performance, we are not saying the government had a

duty to actively advocate for the agreed-upon sentence or to

present     the   recommendation      with     "ruffles   and   flourishes."

Montañez-Quiñones, 
911 F.3d at 65
.            And, as the government points

out in its briefing, in Lessard we held there had been no breach

in part because the plea agreement had not imposed an "affirmative

obligation of either advocacy or explication on the prosecutor"

regarding the agreed-to low-end GSR recommendation.              35 F.4th at

44.   We perceive a difference, however, between advocacy and some

minimal explanation to the district court about why the government

agreed to the specific recommendation, at least when, as here, the

recommended sentence is so drastically below the GSR the government

thought accurately captured the details of the offense at the time

the plea was negotiated.            Remember, even under the TOL of 18

contemplated      in   the   plea   agreement,   the   GSR   would   not   have

authorized probation.         The government agreed to recommend a true

and substantial downward variation, not merely a low-end guideline

sentence.     Moreover, in fulfilling its dual obligations to keep


                                     - 21 -
its bargained for promise to Cortés and concurrently provide

accurate    information        to    the    court,    it    nonetheless     had    an

incontrovertible,       minimal      obligation      not   to    champion   a     more

punitive sentence.          Cf. Gonczy, 
357 F.3d at 53
 (concluding breach

occurred when "the substance of the prosecutor's argument at the

sentencing hearing can only be understood to have emphasized [the

defendant's] wrongdoing and his leadership role in the offense,

advocating for the imposition of a higher sentence than the agree-

upon term"); Wyatt, 982 F.3d at 1030.                Viewed in its totality, we

believe the government's presentation below is best understood as

advocating, in effect, for a more punitive sentencing outcome.

See Frazier, 
340 F.3d at 10
.               In United States v. Brown, 
5 F.4th 913
 (8th Cir. 2021), (a case Cortés brought to our attention) our

sister circuit held the government breached the plea agreement

when it endorsed the higher base offense level presented in the

PSR than the one it and the defendant had mutually agreed upon in

the agreement even though the prosecutor had not specifically

championed a higher sentence at the sentencing hearing than that

spelled    out   in   the    agreement.        
Id. at 916
   ("[A]lthough      the

[g]overnment boasts that it scrupulously adhered to the plea

agreement, its conduct . . . tells a different story." (internal

quotation marks omitted)).           We find Brown's reasoning helpful.

            Given     the    great    disparity      between     probation's      loss

amount calculus and the drastically lower loss amount figure the


                                       - 22 -
parties'   plea   deal   contemplated,     and   given   the   government's

affirmative assent to probation's figures, the district court was

left to speculate about what rationale might reasonably support

such a seemingly off-kilter, well-below guidelines recommendation.

Put differently, the government's failure to provide at least some

explanation for its decision to lend its prestigious imprimatur to

such a dramatic downward variation likely caused the district court

to view the government's "stand by" statement as just hollow words,

undermining   any   notion   that    the   government    viewed   the    plea

agreement as fair and appropriate. Here, the agreed recommendation

in the plea agreement called not for a small difference in degree

of punishment but a categorical difference in kind: probation v.

prison.    In context, the government's reserve here -- tantamount

to a repudiation of the agreement -- implicitly but clearly made

it known to the district court that it could dispense with a

careful consideration of the parties' bargained-for plea agreement

and throw that deal out the window.         See Frazier, 
340 F.3d at 10

(noting    that   this   court      "forbid[s]   end-runs      around"   the

government's promises in the plea agreement); Riggs, 
287 F.3d at 224-25
 (explaining a breach occurred at the sentencing hearing

when the government remained silent about the plea agreement,

including the drug quantity and recommended sentence contemplated

therein); Clark, 
55 F.3d at 12
 (holding the government breached

the plea agreement by implicitly opposing an agreed-upon reduction


                                 - 23 -
in   the    guidelines   calculus     --     "formal   opposition   was   not

necessary"); Brown, 5 F.4th at 916; cf. Ubiles-Rosario, 
867 F.3d at 286-87
 (holding no breach when the government expressed its

recommendation "early, often, and throughout the sentencing").8

So when we ask here "whether the prosecutor's 'overall conduct

[was]      reasonably    consistent    with      making    [the     promised]

recommendation, rather than the reverse,'" Lessard, 35 F.4th at 42

(second alteration in original) (quoting Canada, 
960 F.2d at 269
),

we answer, no.

             Moving along, when a defendant can show a plain violation

of the plea agreement (taking care of plain error prongs 1 and 2),

we proceed to the third prong of plain error review and consider

whether the defendant has shown that the government's breach was

prejudicial to him.      See Gall, 
829 F.3d at 73
 (citing Puckett v.

United States, 
556 U.S. 129, 141-42
 (2009)). This prong "generally

requires the defendant to 'show a reasonable probability that, but




     8 Despite the government's assertion otherwise, United States
v. Gall is distinguishable. In that case, we held, on plain error
review, that there was no breach when the government stated the
guidelines calculation in the PSR (which included two enhancements
not reflected in the plea agreement) was correct and recommended
the top of the GSR agreed to in the agreement. 
829 F.3d 64
, 73-
74 (1st Cir. 2016).     Recommending the top end of the GSR, as
permitted by the terms of a plea agreement despite probation's
calculation of a higher GSR, is not the same circumstance as
promising to recommend a downward departure from the GSR and a
sentence of probation, not incarceration.     Especially when, in
Gall, defense counsel offered their own acknowledgment that the
record correctly supported the GSR presented in the PSR. 
Id.


                                    - 24 -
for the error, the outcome of the proceeding would have been

different.'"       United States v. Canty, 
37 F.4th 775
, 790 (1st Cir.

2022) (quoting Rosales-Mireles v. United States, 
585 U.S. 129
,

134-35 (2018)); see Miranda-Martinez, 
790 F.3d at 275
 (considering

whether the alleged breach had affected the sentencing outcome).

Further, in our evaluation of prejudice we also keep in mind that,

in    agreeing     to   plead     guilty,   a    defendant     waives    important

constitutional      rights      afforded    to   all   criminally       accused;    a

knowing and voluntary surrender of rights "not in exchange for the

actual sentence or impact on the judge, but for the prosecutor's

statements in court."           Correale v. United States, 
479 F.2d 944, 949
 (1st Cir. 1973).        Stated differently, "[t]he quid pro quo from

the defendant's point of view . . . [is] the prestige of the

government and its potential to influence the district court."

United States v. Velez Carrero, 
77 F.3d 11, 11-12
 (1st Cir. 1996).

             As pressed by the government, this court has previously

rejected, in context-specific reviews, certain claims of prejudice

tendered by defendants asserting plea breaches.                 But those cases

are distinguishable from the one we address here.                   In Gall, we

held no prejudice had been shown because defense counsel admitted

at    sentencing    that    the    record   supported    the    PSR's    different

guideline calculation than the one agreed to in the plea agreement

and    the   district      court's   sentencing     explanation     provided       no

indication that it was the prosecutor's statement agreeing with


                                      - 25 -
the PSR's guidelines calculation which influenced the court's

decision. 
829 F.3d at 74
. In Sierra-Jiménez, this court concluded

the plea-agreement-breach claim failed because nothing in the

record "suggest[ed] . . . that the district court would have

imposed [the requested] sentence if the government had uttered

such recommendation."        93 F.4th at 570-71.        In the case at hand,

defense counsel, unlike counsel in Gall, made no concession that

the PSR accurately reflected the appropriate loss amount and

resulting guidelines calculation.             Moreover, the district court

clearly announced (before pronouncing Cortés' sentence) that it

had   considered    (among    other    things)    the     "arguments     by   the

prosecutor and the defense counsel" and that the sentencing factors

pursuant to § 3553(a) would not be met by a sentence of probation.

           In    addition,    the   government    deprived     Cortés    of    its

potential influence over the imposed sentence by neglecting to

vocalize   any     reasons    for   agreeing     to   the    below-guidelines

recommendation.        See Velez Carrero, 
77 F.3d at 12
.             As Cortés

emphasizes, had the government provided some explanation for the

disparity in     the    loss amount calculation and why             it   thought

probation was the appropriate punishment for Cortés in this case

or which § 3553(a) factors shaped its view of the case, there was

a   reasonable   probability    that    the    district     court   would     have

sentenced differently.         Therefore, in our view of the record,




                                    - 26 -
Cortés has shown the government's breach resulted in prejudice to

him.   See Rosales-Mireles, 585 U.S. at 134-35.

            So we march on to the fourth prong, examining whether

"the error adversely impacted the fairness, integrity, or public

reputation of judicial proceedings."          Sierra-Jiménez, 93 F.4th at

570.     We are convincingly satisfied that it did.           Cortés argues

that allowing the government's breach here to go uncorrected would

affect the integrity of the justice system because it would lose

credibility, the very tenet on which the plea-bargaining system is

based.    We agree because, as we've stated before, "violations of

plea agreements on the part of the government serve not only to

violate the constitutional rights of the defendant, but directly

involve the honor of the government, public confidence in the fair

administration of justice, and the effective administration of

justice in a federal scheme of government."           Riggs, 
287 F.3d at 226
 (quoting United States v. McQueen, 
108 F.3d 64, 66
 (4th Cir.

1997))    (concluding   that   the    government's   breach   of   the   plea

agreement met the fourth prong of plain error review).

                    WHERE THE CASE GOES FROM HERE

            For the reasons explained above, the government breached

the plea agreement during the sentencing hearing.             The district

court's judgment is therefore vacated, and we remand this case for

further proceedings before a different district court judge.              See

Brown, 5 F.4th at 917 (applying the same disposition after holding


                                     - 27 -
the government breached the plea agreement); Riggs, 
287 F.3d at 226
 (same); Clark, 
55 F.3d at 15
 (same).9




     9 The Bureau of Prisons' electronic database for the location
of inmates shows that Cortés was released from incarceration in
early April, about one month after oral argument in this case. In
the intervening period, neither party has suggested that his appeal
is moot. And, in fact, his release does not automatically moot
this appeal, given that Cortés is still serving a three-year term
of supervised release and is subject to a restitution order based
on the higher total loss amount in the PSR. See United States v.
Reyes-Barreto, 
24 F.4th 82
, 84-86 (1st Cir. 2002).


                              - 28 -


Reference

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