United States Court of Appeals

For the First Circuit

No. 21-1443

UNITED STATES OF AMERICA,

Appellee,

v.

STEVEN LESSARD, a/k/a Shawn,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF NEW HAMPSHIRE

[Hon. Joseph N. Laplante, U.S. District Judge]

Before

Barron, Chief Judge,

Selya and Kayatta, Circuit Judges.

Mark W. Shea and Shea & LaRocque, LLP on brief for appellant.

John J. Farley, United States Attorney, and Seth R. Aframe, 

Assistant United States Attorney, on brief for appellee.

May 23, 2022
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SELYA, Circuit Judge. Defendant-appellant Steven 

Lessard challenges his 150-month prison sentence and seeks 

resentencing on the ground that the government breached his plea 

agreement (the Agreement). Specifically, he asserts that the 

government broke its promise to recommend a sentence at the low 

end of the applicable guideline range by asking the sentencing 

court to impose a "big sentence." Relatedly, he argues that this 

alleged breach defeats a waiver-of-appeal provision in the 

Agreement that seemingly blocks his path.

Whether the government's breach of a plea agreement 

voids a waiver-of-appeal provision within a plea agreement is a 

question of novel impression in this circuit. But we need not 

answer that novel question today: even if we assume, favorably to 

the defendant, that the waiver-of-appeal provision is inoperative 

in his case, the defendant's claim of breach fails. Consequently, 

we affirm the judgment below.

I. BACKGROUND

We briefly rehearse the relevant facts and travel of the 

case. When — as in this case — a sentencing appeal follows a 

guilty plea, "[w]e draw the facts from the plea agreement, the 

change-of-plea colloquy, the presentence investigation report (PSI 

Report), and the transcript of the disposition hearing." United 

States v. Almonte-Nuñez, 771 F.3d 84, 86 (1st Cir. 2014).
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In March of 2017, Drug Enforcement Administration (DEA) 

agents identified a drug-trafficking organization that distributed 

fentanyl throughout the Merrimack Valley region (a part of which 

lies in New Hampshire and a part of which lies in Massachusetts).

During the subsequent investigation, DEA agents conducted

surveillance and (pursuant to a warrant) intercepted telephone

calls. These intercepted calls included calls during the period 

from January 29 to March 14, 2018 between the defendant and Sergio 

Martinez (the leader of the drug-trafficking organization). The 

agents listened to calls in which Martinez and the defendant 

arranged deliveries of fentanyl to the defendant's apartment in 

Lawrence, Massachusetts. 

On March 14, local police officers executed a search 

warrant for the defendant's apartment. Once inside, they found

(among other things) more than 50 grams of fentanyl and over $2,000 

in cash. In the basement of the building, the searchers recovered

more than 2,000 grams of fentanyl and several firearms.

The following week, a federal grand jury sitting in the 

District of New Hampshire returned an indictment that charged the 

defendant (and others) with conspiracy to distribute and to possess 

with intent to distribute controlled substances. See 21 U.S.C. 

§§ 841, 846. Although three superseding indictments eventuated, 

the charge against the defendant remained constant. The defendant 
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initially maintained his innocence but — on the eve of trial — he 

reversed course and entered into the Agreement with the government. 

Under the terms of the Agreement, the defendant agreed 

to plead guilty to the single charge against him. In consideration 

of his plea, the government agreed, as relevant here, to "recommend 

a sentence at the bottom of the applicable advisory guideline 

range." The Agreement contained a waiver-of-appeal provision, 

which stated that the defendant waived his "right to challenge his 

guilty plea and/or sentence on direct appeal" so long as the 

sentencing court imposed a sentence within or below the applicable 

guideline range. 

The district court held the change-of-plea hearing on 

September 30, 2019. During the ensuing colloquy, the court 

confirmed that the defendant understood the rights that he was

surrendering by pleading guilty. The court also reviewed with the 

defendant the terms of the waiver-of-appeal provision. After 

questioning the defendant regarding the voluntariness of his 

guilty plea, the court accepted the plea. In doing so, the court

determined "that [the defendant] ha[d] entered the plea 

competently and voluntarily based on a full knowledge of the 

charges against him and the consequences of his plea."

The PSI Report was subsequently prepared. The probation 

officer recommended a total offense level (TOL) of 41 and a 

criminal history category (CHC) of III. These calculations yielded 
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a proposed guideline sentencing range of 360 months to life 

imprisonment.

At the disposition hearing, the district court first 

addressed six "disputed issues." Some of these issues comprised 

objections to the PSI Report. Among the other issues was "the 

defendant's request for a variance below the guideline sentencing 

range." After resolving some of the disputed issues, the district 

court lowered the TOL to 31 and confirmed the defendant's placement 

in CHC III. These revised calculations yielded a guideline

sentencing range of 135 to 168 months of imprisonment. The court 

then heard arguments of counsel (including arguments for and

against a downward variance) and the defendant's allocution.

The prosecutor began by stating that "[i]n accordance 

with the plea agreement, we recommend a sentence at the low end of 

the guidelines." Then — referring to the defendant's request for 

a downward variance — the prosecutor added that "[w]e are opposed 

to any variance in this case." The prosecutor proceeded to argue 

against a below-the-range sentence, stating that the defendant was 

"a recidivist drug dealer" who "was rocking and rolling in Lowell 

as a big-time drug dealer."1 He observed that while the defendant 

was "not the biggest guy in this big federal case," he was "the 

biggest customer of the big guy." As such, the circumstances in 

1 Lowell is a Massachusetts city within the Merrimack Valley 

region. 
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the defendant's case "require[d] a big sentence." The prosecutor 

concluded by stating that "consistent with our obligation in the 

plea agreement, we recommend a sentence in the guideline range." 

Following the defendant's allocution, the court heard 

from defense counsel, who again requested a downwardly variant 

sentence. The court responded that "a variance would be unjust" 

in the defendant's case because "none of [the] normal things that 

militate toward leniency except for the fact that [the defendant] 

served pretrial detention during COVID . . . is present here." 

Even so, the court observed that detention during the pandemic was 

"burdensome" and, as such, it required "a measure of leniency and 

mercy." As a result, the court stated that it would forgo its 

"intention" to sentence the defendant "at the high end of the 

range." When all was said and done, the court imposed a mid-range 

sentence: a 150-month term of immurement. In the process, the 

court analyzed each of the relevant sentencing factors. See 18 

U.S.C. § 3553(a).

This timely appeal ensued.

II. ANALYSIS

The defendant's appeal begins — and ends — with his claim 

that the government breached the terms of the Agreement. 

Specifically, the defendant contends that the Agreement's waiverof-appeal provision does not apply because the government breached 
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the Agreement and, thus, invalidated the waiver-of-appeal 

provision. This contention is unavailing.

To be sure, the defendant's line of argument has 

considerable grounding. After all, the government's breach of a 

plea agreement may be a ground for either resentencing or 

withdrawal of a guilty plea. See United States v. Gonczy, 357 

F.3d 50, 52 (1st Cir. 2004); United States v. Clark, 55 F.3d 9, 14 

(1st Cir. 1995); United States v. Canada, 960 F.2d 263, 271 (1st 

Cir. 1992). And we have said that "a waiver should [not] be 

construed to bar an appeal" of a sentence "that violates a material 

term of [a] plea agreement." United States v. Teeter, 257 F.3d 

14, 25 n.10 (1st Cir. 2001); see Correale v. United States, 479 

F.2d 944, 949 (1st Cir. 1973) (holding that prosecutor's failure 

to fulfill promise given in exchange for waiver of right to contest 

charges renders waiver ineffective). In addition, several courts 

of appeals have held that a waiver-of-appeal provision in a plea 

agreement is unenforceable when the government has breached that 

agreement. See, e.g., United States v. Gonzalez, 309 F.3d 882, 

886 (5th Cir. 2002); United States v. Bowe, 257 F.3d 336, 342 (4th 

Cir. 2001); United States v. Gonzalez, 16 F.3d 985, 989-90 (9th 

Cir. 1993).

Whether a prosecutor's breach of a plea agreement 

negates a waiver-of-appeal provision in a plea agreement presents 

a question of first impression in this circuit. But it is a 
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question that we need not answer today. Cf. Privitera v. Curran

(In re Curran), 855 F.3d 19, 22 (1st Cir. 2017) ("[C]ourts should 

not rush to decide unsettled issues when the exigencies of a 

particular case do not require such definitive measures."). Even 

if we assume — favorably to the defendant — that the waiver-ofappeal provision may be invalidated by a breach of the Agreement, 

his appeal falters: there was no breach here.

In many cases, the question of whether the government 

breached the terms of a plea agreement is a question of law, 

engendering de novo review. See, e.g., Almonte-Nuñez, 771 F.3d at 

89. But where, as here, the defendant fails to object to the 

purported breach in the court below, review is for plain error. 

See Puckett v. United States, 556 U.S. 129, 131, 143 (2009). 

Plain error is "a formidable standard of appellate 

review." United States v. Saxena, 229 F.3d 1, 5 (1st Cir. 2000). 

To prevail on plain-error review, the defendant must carry the 

devoir of persuasion as to four elements: "(1) that an error 

occurred (2) which was clear or obvious and which not only (3) 

affected the defendant's substantial rights, but also (4) 

seriously impaired the fairness, integrity, or public reputation 

of judicial proceedings." United States v. Duarte, 246 F.3d 56, 

60 (1st Cir. 2001); see United States v. Olano, 507 U.S. 725, 732 

(1993). The defendant cannot shoulder this heavy burden in the 

case at hand. 
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The foundational principles that govern this appeal are 

uncontroversial. "[W]hen a plea rests in any significant degree 

on a promise or agreement of the prosecutor, so that it can be 

said to be part of the inducement or consideration, such promise 

must be fulfilled." Santobello v. New York, 404 U.S. 257, 262 

(1971). "Because plea bargaining requires defendants to waive 

fundamental constitutional rights, we hold prosecutors engaging in 

plea bargaining to 'the most meticulous standards of both promise 

and performance.'" Clark, 55 F.3d at 12 (quoting Correale, 479 

F.2d at 947). "Such standards require more than lip service to, 

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

Almonte-Nuñez, 771 F.3d at 89. "[A] defendant is entitled . . . to 

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

faith of the prosecutor." United States v. Matos-Quiñones, 456 

F.3d 14, 24 (1st Cir. 2006) (internal quotation and citation 

omitted). 

We have noted before that there is "[n]o magic formula" 

for assessing whether a prosecutor has fulfilled his obligation 

under the terms of a plea agreement to recommend a particular 

sentence. Gonczy, 357 F.3d at 54. When making this assessment, 

we must "consider the totality of the circumstances." AlmonteNuñez, 771 F.3d at 91. The critical question is whether the 

prosecutor's "overall conduct [is] reasonably consistent with 
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making [the promised] recommendation, rather than the reverse." 

Canada, 960 F.2d at 269. 

In answering this critical question, we remain mindful 

that the government's obligation to fulfill promises made in a 

plea agreement does not exist in isolation. See United States v. 

Colón-Rosario, 921 F.3d 306, 312 (1st Cir. 2019); Almonte-Nuñez, 

771 F.3d at 90. The government, for example, has a "corollary 

duty to provide full and accurate information about the offense 

and the offender to the sentencing court." Almonte-Nuñez, 771 

F.3d at 86. Moreover, when the plea agreement allows the 

government to advocate for a sentence that is stiffer than the 

sentence that defense counsel has proposed, the government "ha[s] 

a right (indeed, a duty) to explain to the court why the higher 

sentence that it [i]s urging [i]s more appropriate." United States

v. Montañez-Quiñones, 911 F.3d 59, 65 (1st Cir. 2018). The obverse 

is also true: the government has a right to explain to the court 

why a sentence that the prosecutor had not agreed to recommend is 

inappropriate. See id. And in either event, "the government is 

not constrained to pull its punches." Id.

In this case, neither party disputes that the government 

agreed to recommend a sentence at the bottom of the applicable 

guideline range. The defendant strives to persuade us, though, 

that the government attempted an end run around its obligation by

giving lip service to its promise — recommending a sentence at the 
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low end of the guideline range — and then "vigorously advocating 

for 'a big sentence.'" We are not convinced. 

Although it is true that the prosecutor stated that the 

defendant's offense warranted a "big sentence," the defendant

glosses over the context in which this statement was made. Context 

matters, see Saxena, 229 F.3d at 7-8; Canada, 960 F.2d at 269-70, 

and the key component of the context here is that the defendant 

argued, in his sentencing memorandum, for a downwardly variant 

sentence. What is more, the court expressly acknowledged this 

request early in the disposition hearing. Subsequently — when 

asked for his sentencing recommendation — the prosecutor complied 

with his obligation under the Agreement by telling the court that 

he recommended "a sentence at the low end of the guidelines." He

then proceeded to argue in "oppos[ition] to any variance,"

explaining why the defendant's criminal history and the offense of 

conviction made a downwardly variant sentence inappropriate. He

concluded this portion of his argument by stating that the 

defendant's conduct "require[d] a big sentence. And so, consistent 

with our obligation in the plea agreement, we recommend a sentence 

in the guideline range."2

2 Taken in a vacuum, this last sentence might be problematic. 

In context, however, we are satisfied that it was merely another

way of expressing the prosecutor's view that the district court 

should not grant a downwardly variant sentence. And at any rate, 

a sentence at the bottom of the applicable range of 135 to 168 

months is certainly a "big sentence."
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Seen in this light, the prosecutor's statement that the 

offense of conviction "require[d] a big sentence" was simply an 

expression of his view that a downwardly variant sentence would be 

inappropriate. Nothing in the Agreement operated to muzzle such 

an argument. Consequently, we conclude that, under the demanding 

plain-error standard, the defendant has failed to show that the 

prosecutor's "overall conduct" was other than "reasonably 

consistent with making [the promised] recommendation." Canada, 

960 F.2d at 269.

Our precedent strongly supports this conclusion. We 

have refused to find a breach of a plea agreement in analogous

circumstances. In Almonte-Nuñez, for example, the government 

agreed to recommend a sentence at the high end of the applicable 

guideline range and not to argue for upward offense-level 

adjustments. 771 F.3d at 86. At the disposition hearing — in 

response to defense counsel's request for a more lenient sentence 

— the prosecutor "referenced the seriousness of the offenses, the 

various aggravating factors, and the need for deterrence." Id. at 

87. The defendant appealed the ensuing sentence, contending that 

the prosecutor had breached the plea agreement by making statements

that allegedly supported additional guideline enhancements. See

id. at 89. Reviewing for plain error, we rejected that contention

and held that the prosecutor did not breach the plea agreement

merely by "emphasizing facts that made a sentence at the low end 
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of [the guideline range] inappropriate." Id. at 91. The 

prosecutor's conduct, we concluded, was "within fair territory." 

Id. The same is true here: the prosecutor's argument in 

opposition to a downwardly variant sentence constituted

permissible advocacy consistent with the Agreement. 

The defendant has a fallback position. He argues —

albeit in conclusory fashion — that the prosecutor breached the 

Agreement "[b]y failing to advocate for a low-end sentence" and 

"never explain[ing] why a low-end guideline sentence was 

appropriate." Here, however, the Agreement imposed no affirmative 

obligation of either advocacy or explication on the prosecutor

but, rather, imposed an obligation to recommend a low-end guideline

sentence. The prosecutor fulfilled that obligation.3 And as we 

have said, "a prosecutor is not obliged to present an agreed 

recommendation either with ruffles and flourishes or 'with any

particular degree of enthusiasm.'" Montañez-Quiñones, 911 F.3d at 

65 (quoting Canada, 960 F.2d at 270).

To say more would be to paint the lily. On plain-error 

review, we cannot say that the prosecutor breached either the 

letter or the spirit of the Agreement merely by highlighting facts 

3 The defendant gestures at an argument that the government's 

commitment to "recommend a sentence at the bottom of the applicable 

advisory guideline range" required it to ask explicitly for a 135-

month prison sentence. This argument is undeveloped and, 

therefore, we deem it waived. See United States v. Zannino, 895 

F.2d 1, 17 (1st Cir. 1990).
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that made a downwardly variant sentence inappropriate. The upshot, 

then, is that there was no breach of the Agreement. 

III. CONCLUSION

We need go no further. For the reasons elucidated above, 

the judgment below must be 

Affirmed.