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 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,

(1st Cir. 2014).

- 2 - 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

, 846. Although three superseding indictments eventuated,

the charge against the defendant remained constant. The defendant

- 3 - 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

- 4 - 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

1Lowell is a Massachusetts city within the Merrimack Valley region.

- 5 - 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

(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 waiver-

of-appeal provision does not apply because the government breached

- 6 - 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,

(1st Cir. 2004); United States v. Clark,

(1st Cir. 1995); United States v. Canada,

(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,

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

(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,

(5th Cir. 2002); United States v. Bowe,

(4th

Cir. 2001); United States v. Gonzalez,

(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

- 7 - question that we need not answer today. Cf. Privitera v. Curran

(In re Curran),

(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-of-

appeal 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,

. 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,

(2009).

Plain error is "a formidable standard of appellate

review." United States v. Saxena,

(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,

(1st Cir. 2001); see United States v. Olano,

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

case at hand.

- 8 - 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,

(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,

(quoting Correale,

). "Such standards require more than lip service to,

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

Almonte-Nuñez,

. "[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,

(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,

. When making this assessment,

we must "consider the totality of the circumstances." Almonte-

Nuñez,

. The critical question is whether the

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

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

Canada,

.

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,

(1st Cir. 2019); Almonte-Nuñez,

. 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,

. 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,

(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

And in either event, "the government is

not constrained to pull its punches."

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

- 10 - 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,

; Canada,

,

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

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

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."

- 11 - 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,

.

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.

. 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."

. 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

. 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

- 12 - of [the guideline range] inappropriate."

. The

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

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,

(quoting Canada,

).

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

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

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,

(1st Cir. 1990).

- 13 - 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.

- 14 -