United States v. Maldonado Villeda

• Court: Court of Appeals for the Second Circuit
• Decided: June 17, 2026
• Docket: 25-1748
• Status: Unpublished

Opinion

25-1748 United States v. Maldonado Villeda

UNITED STATES COURT OF APPEALS FOR THE SECOND CIRCUIT

SUMMARY ORDER

RULINGS BY SUMMARY ORDER DO NOT HAVE PRECEDENTIAL EFFECT. CITATION TO A SUMMARY ORDER FILED ON OR AFTER JANUARY 1, 2007, IS PERMITTED AND IS GOVERNED BY FEDERAL RULE OF APPELLATE PROCEDURE 32.1 AND THIS COURT’S LOCAL RULE 32.1.1. WHEN CITING A SUMMARY ORDER IN A DOCUMENT FILED WITH THIS COURT, A PARTY MUST CITE EITHER THE FEDERAL APPENDIX OR AN ELECTRONIC DATABASE (WITH THE NOTATION “SUMMARY ORDER”). A PARTY CITING TO A SUMMARY ORDER MUST SERVE A COPY OF IT ON ANY PARTY NOT REPRESENTED BY COUNSEL.

At a stated term of the United States Court of Appeals for the Second Circuit, held at the Thurgood Marshall United States Courthouse, 40 Foley Square, in the City of New York, on the 17th day of June, two thousand twenty-six.

PRESENT:

RICHARD C. WESLEY, RICHARD J. SULLIVAN, JOSEPH F. BIANCO, Circuit Judges. _____________________________________

UNITED STATES OF AMERICA,

Appellee,

v. No. 25-1748

FREDY ARMANDO MALDONADO VILLEDA,

Defendant-Appellant. _____________________________________ For Defendant-Appellant: EDWARD ZAS, Federal Defenders of New York, Appeals Bureau, New York, NY.

For Appellee: BRANDON G. DAVIS (Dylan A. Stern, on the brief), Assistant United States Attorneys, for Joseph Nocella, Jr., United States Attorney for the Eastern District of New York, Brooklyn, NY.

Appeal from a judgment of the United States District Court for the Eastern

District of New York (Gary R. Brown, Judge).

UPON DUE CONSIDERATION, IT IS HEREBY ORDERED,

ADJUDGED, AND DECREED that the July 14, 2025 judgment of the district court

is AFFIRMED.

Fredy Armando Maldonado Villeda (“Maldonado”) appeals a judgment of

conviction following his plea of guilty to one count of illegally reentering the

United States in violation of 8 U.S.C. §§ 1326(a) and 1326(b)(1), for which he was

sentenced to thirty-six months’ imprisonment to be followed by one year of

supervised release. On appeal, Maldonado contends that the government

breached its plea agreement by arguing for an “upward departure” from

Maldonado’s Sentencing Guidelines range of ten to sixteen months’ imprisonment

“despite the absence of any new information and despite [the government’s]

express promise not to seek such a departure.” Maldonado Br. at 2–3; see App’x

2 at 10–15 (plea agreement). The government’s breach, Maldonado argues,

requires vacatur of his sentence and a remand “for resentencing before a different

judge.” Maldonado Br. at 4. We assume the parties’ familiarity with the

underlying facts, procedural history, and issues on appeal, to which we refer only

as necessary to explain our decision.

“We review interpretations of plea agreements de novo and in accordance

with principles of contract law.” United States v. Riera, 298 F.3d 128, 133 (2d Cir.

2002). Determining “whether a plea agreement has been breached” is a context-

specific inquiry, and we “look to the reasonable understanding of the parties as to

the terms of the agreement,” id. (alteration adopted and internal quotation marks

omitted), examining both the “precise terms of the plea agreement[]” and the

“parties’ behavior,” United States v. Wilson, 920 F.3d 155, 163 (2d Cir. 2019). We

also “construe plea agreements strictly against the [g]overnment” because it is

“usually the party that drafts the agreement” and ordinarily possesses “awesome

advantages in bargaining power.” United States v. Padilla, 186 F.3d 136, 140

(2d Cir. 1999). Accordingly, we resolve “any ambiguities in the agreement . . . in

favor of the defendant.” Riera, 298 F.3d at 133.

3 Applying these principles, we have observed that “the government’s

commentary” at sentencing may constitute a breach if it “reasonably appears to

seek to influence the court in a manner incompatible with the agreement, . . .

notwithstanding formal language of disclaimer.” United States v. Amico, 416 F.3d

163, 167 n.2 (2d Cir. 2005). But even the government’s remarks will not qualify as

a breach if (i) they are “in response to a specific inquiry from the court”; (ii) “the

plea agreement provide[s] that the government c[an] respond to the court’s

inquiries”; and (iii) “the government later . . . emphasize[s] that it was not

advocating” for conditions that would constitute a breach. Riera, 298 F.3d at 134.

As evidence of the breach of the plea agreement, Maldonado points to the

government’s statements at sentencing that (i) “[he] had previously received a

[forty-one]-month sentence for the same offense,” which in the government’s view

should trigger a “ratcheting[-]up effect,” Maldonado Br. at 19–20 (quoting App’x

at 65), since “[e]very time you commit the same offense the punishment should

increase,” App’x at 65; and (ii) Maldonado’s “criminal history score” understated

“the extent and seriousness of his [criminal] record,” Maldonado Br. at 20; see also

App’x at 65 (prosecutor stressing that “for [Maldonado] to return before [the court]

4 and be facing ten to [sixteen] months flies in the face of accepted principles [of]

criminal law”). 1

Maldonado contends that the government’s arguments meet “the standard

for upward departure(s)” set forth in the Guidelines, see U.S.S.G. § 4A1.3(a)(1)

(Nov. 1, 2024 ed.), and therefore constituted an “encouraged basis” for departing

upward from the Guidelines range, United States v. Gayle, 389 F.3d 406, 409 (2d Cir.

2004) (internal quotation marks omitted). But while the government’s comments

at sentencing may have strayed “too close in tone and substance to forbidden

advocacy to have been well-advised,” United States v. Griffin, 510 F.3d 354, 362 (2d

Cir. 2007) (internal quotation marks omitted), we cannot say that they run afoul of

the lines drawn in Riera, see 298 F.3d at 134–36.

First, the government’s comments at sentencing “w[ere] in response to a

specific inquiry from the court.” Id. at 134. At the outset of sentencing, the

district court correctly calculated Maldonado’s Guidelines range, but it remarked

that Maldonado’s “Criminal History Category of III” was “unusual[ly]” low given

1 After the district court indicated at sentencing that it would vary from Maldonado’s Guidelines range, his counsel asked for “a further opportunity” to address the issues raised by the court. App’x at 75. The district court therefore agreed to postpone sentencing, the parties filed supplemental sentencing submissions, and a second sentencing hearing was held four months later. As relevant here, the disputed statements were all made during the first sentencing hearing.

5 his lengthy criminal history. App’x at 155. In particular, the district court noted

that Maldonado’s 2010 conviction for felony robbery – which involved

“attack[ing]” an eighty-seven-year-old landlord and stealing “$24,000 in rent

payments,” id. at 71; PSR ¶ 24 – did not count for purposes of his current

Guidelines range because it was over ten years old. It was only after the district

court queried whether the government wished “to say anything” before it

imposed sentence, App’x at 64, that the prosecutor “acknowledge[d] a point that

your Honor brought up,” id. at 62, “in terms of the complicated criminal history in

this case,” id. at 68. Because the government’s remarks were made only after the

district court expressed skepticism that the Guidelines properly accounted for “the

seriousness of [Maldonado’s] prior offenses” and his “pattern of recidivism,” id.

at 73, the government’s statements do not suggest a breach of the plea agreement.

See United States v. Goodman, 165 F.3d 169, 173 (2d Cir. 1999) (refusing to find

breach of plea agreement when “it was [the district court], not the [g]overnment,

who raised questions about” relevant sentencing adjustments).

Second, “the plea agreement provided that the government could respond

to the court’s inquiries.” Riera, 298 F.3d at 134. The agreement emphasized that

the “[U.S. Attorney’s] Office will advise the [c]ourt and the Probation Department

6 of information relevant to sentencing, including criminal activity engaged in by

the defendant, and such information may be used by the [c]ourt in determining

the defendant’s sentence.” App’x at 11 (“No limitation shall be placed on the

information concerning the background, character, and conduct of a person

convicted of an offense [that] a court of the United States may receive and consider

for the purpose of imposing an appropriate sentence.” (quoting 18 U.S.C. § 3661)).

The district court understood as much, and it construed the government’s

representations at sentencing as “consistent” with its “obligations to the court”

and “more importantly,” under “the [plea] agreement” itself, to provide

“information relevant to sentencing,” id. at 68, as the court weighed the “statutory

requirement[s]” of 18 U.S.C. § 3553(a), id. at 74.

Moreover, even though the government “typically” drafts plea agreements

to include a provision barring it from arguing for “a sentence on the higher range

of the [G]uidelines,” that stipulation was “specifically removed” from

Maldonado’s plea agreement. Id. at 69. And since “nothing in the plea

agreement barred the government from forcefully advocating for a sentence at the

top of the [Guidelines] range,” the prosecutor was free to “cast[] pejorative light

on [Maldonado] and his criminal activity” without running afoul of the

7 agreement’s terms. Amico, 416 F.3d at 165. Put simply, the government did not

breach the plea agreement by responding to the district court’s inquiries about

“the highly unusual factors” of Maldonado’s case that “distinguish[ed] it from the

bulk of the many [other] cases.” 2 App’x at 70.

Third and finally, the government “repeatedly emphasized that it was not

advocating [for] an upward departure” in violation of the plea agreement – at both

sentencing hearings and in its written submissions. Riera, 298 F.3d at 134; see, e.g.,

App’x at 68 (“I am not moving for an upward departure.”); id. at 69 (“[W]e are [in]

no way moving for an upward departure.”); id. at 96 (government’s supplemental

sentencing memorandum “recommend[ing] a sentence within the Guidelines

range of [six] to [ten] months’ imprisonment”); 3 id. at 165 (district court

acknowledging “that [the government] hadn’t made a motion for an upward

departure”). Instead, the prosecutor explained that “any statements that [she]

2 Because there was “already . . . a suggestion that the government was violating the plea agreement” at the first sentencing hearing, the district court – to eliminate any doubt – expressly limited the government to providing “facts only” in its supplemental sentencing submission. App’x at 77–78; see id. at 78 (“I don’t want to hear numbers from [the government]. I don’t want to hear months. I don’t want to hear anything about how long [Maldonado’s sentence] should be.”).

3 The government has indicated on appeal that its supplemental sentencing memorandum “erroneously understat[ed] the applicable [Guidelines] range as [six] to [ten] months’ imprisonment,” Gov’t Br. at 34, rather than ten to sixteen months’ imprisonment, PSR ¶ 64.

8 ha[d] ever made” were geared toward “the appropriateness of a sentence on the

higher” end of the Guidelines range, id., which, again, was not barred by the plea

agreement, see id. at 164. That the government “soon thereafter . . . repeatedly

told the district court that it had not intended to advocate and was not advocating

a departure,” Riera, 298 F.3d at 136, differentiates this case from United States v.

Griffin, where the “government did nothing to retract its questionable statements

or otherwise ameliorate their impact” to “cure any breach,” 510 F.3d at 365 (citing

Amico, 416 F.3d at 165).

Though “statements by the government asserting that it did not intend to

violate the plea agreement ‘do not insulate [it] against a finding of breach if in fact

what was said constituted an argument’ that violated the plea agreement,” id.

(alteration adopted) (quoting United States v. Vaval, 404 F.3d 144, 153 (2d Cir.

2005)), our inquiry in this area is necessarily context-specific. Here, the

government’s repeated clarifications were sufficient “to clear up any confusion as

to any possible implicit message of advocacy.” Riera, 298 F.3d at 136.

In sum, on this record – where the district court raised the criminal-history

concern first, the plea agreement permitted the government to provide sentencing

information and advocate for the top of the Guidelines range, and the government

9 clarified its position before sentence was imposed and reaffirmed it at a second

hearing – the government’s remarks did not breach the plea agreement. 4 See id.

at 134.

* * *

We have considered Maldonado’s remaining arguments and find them to

be without merit. Accordingly, we AFFIRM the judgment of the district court.

FOR THE COURT: Catherine O’Hagan Wolfe, Clerk of Court

4 Because we conclude that the government did not breach the agreement, we have no occasion to decide whether any breach could be excused as harmless.