22-1871-cr

United States v. Ovalle-Then

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 26th day of September, two thousand twenty-three.

PRESENT:

JOSEPH F. BIANCO,

BETH ROBINSON,

ALISON J. NATHAN,

Circuit Judges.

_____________________________________

United States of America,

Appellee,

v. 22-1871-cr

Samile Ovalle-Then, AKA Samil J. Ovalle,

Defendant-Appellant.

_____________________________________

FOR DEFENDANT-APPELLANT: Melissa A. Tuohey, Assistant Federal Public 

Defender, Office of the Federal Public 

Defender, Syracuse, NY.

FOR APPELLEE: Thomas R. Sutcliffe, Assistant United States 

Attorney, for Carla B. Freedman, United States 

Attorney for the Northern District of New York, 

Syracuse, NY.
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Appeal from a judgment of the United States District Court for the Northern District of 

New York (Sannes, C.J.).

UPON DUE CONSIDERATION, IT IS HEREBY ORDERED, ADJUDGED, AND 

DECREED that the judgment of the district court is AFFIRMED.

Defendant-appellant Samile Ovalle-Then appeals from the district court’s judgment,

entered on August 26, 2022, following his guilty plea pursuant to a plea agreement, to illegal reentry after a conviction of an aggravated felony in violation of 8 U.S.C. § 1326(a) and (b)(2). The 

district court sentenced Ovalle-Then to fifteen months’ imprisonment followed by one year of

supervised release. Ovalle-Then challenges the procedural reasonableness of the sentence only as 

it pertains to the imposition of the term of supervised release. 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 to affirm.

As a threshold matter, we conclude that, due to the waiver of right to appeal in his plea 

agreement, Ovalle-Then has waived any argument that the district court committed procedural 

error when it imposed the term of supervised release. “Waivers of the right to appeal a sentence 

are presumptively enforceable.” United States v. Arevalo, 628 F.3d 93, 98 (2d Cir. 2010). 

Waivers are found to be unenforceable “only in very limited situations, such as when the waiver 

was not made knowingly, voluntarily, and competently, when the sentence was imposed based on 

constitutionally impermissible factors, such as ethnic, racial or other prohibited biases, when the 

government breached the plea agreement, or when the sentencing court failed to enunciate any 
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rationale for the defendant’s sentence.” Id. (internal quotation marks omitted).1 Thus, these 

exceptions “occupy a very circumscribed area of our jurisprudence,” and “we have upheld waiver 

provisions even in circumstances where the sentence was conceivably imposed in an illegal 

fashion or in violation of the Guidelines, but yet was still within the range contemplated in the 

plea agreement.” United States v. Gomez-Perez, 215 F.3d 315, 319 (2d Cir. 2000); accord United 

States v. Ojeda, 946 F.3d 622, 629 (2d Cir. 2020). 

In his plea agreement, Ovalle-Then “waive[d] . . . any and all rights . . . to appeal . . . [a]ny 

sentence to a term of supervised release within the maximum permitted by law.” App’x at 13–

14. Here, the statutory maximum term of supervised release permitted by law is three years. See 

8 U.S.C. § 1326(b)(2); 18 U.S.C. §§ 3583(b)(2), 3559(a)(3). Thus, the imposition of a one-year 

term falls within the appellate waiver as to his supervised release term. 2 The record also 

demonstrates that this waiver was made knowingly, voluntarily, and competently. At the plea 

proceeding, the district court advised Ovalle-Then of the appeal waiver provision, and he 

confirmed that the provision was translated to him, that he discussed it with his attorney, and that 

he understood it. He also confirmed that no one had threatened him or, apart from what was 

contained in the plea agreement, made any promises to him to induce him to plead guilty or sign 

the agreement. Ovalle-Then has made no argument as to why any exception to enforcement of 

1 Moreover, the waiver of appeal in a plea agreement is governed by contract law principles and, thus, is 

unenforceable if the agreement lacked consideration. See United States v. Lutchman, 910 F.3d 33, 37 (2d 

Cir. 2018).

2 We note that Ovalle-Then’s fifteen-month term of imprisonment exceeded the waiver in the plea 

agreement of his right to appeal a term of imprisonment of twelve months or less. However, Ovalle-Then 

does not challenge the term of imprisonment on appeal, and, thus, that component of his sentence does not

affect the enforceability of the appellate waiver as it relates to his term of supervised release.
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the waiver should apply (and, in fact, did not address the appeal waiver in his briefing), nor has 

our own independent review of the record identified any basis for not enforcing the waiver. And 

although Ovalle-Then challenges the one-year term of supervised release as procedurally 

unreasonable, this Court has repeatedly enforced appeal waivers in the face of similar procedural 

challenges. See, e.g., United States v. Buissereth, 638 F.3d 114, 117 (2d Cir. 2011); United States 

v. Yemitan, 70 F.3d 746, 747–48 (2d Cir. 1995). Accordingly, Ovalle-Then’s plea agreement is 

enforceable and precludes this procedural challenge to his term of supervised release.

Even if we were to ignore his appellate waiver and consider his challenge, we would reject 

his claim on the merits. Ovalle-Then contends that the district court’s imposition of a one-year

term of supervised release is procedurally unreasonable because the district court failed to 

consider the Guidelines pertaining to supervised release or other factors listed in 18 U.S.C. § 

3553(a). In particular, Ovalle-Then asserts that the district court “did not adequately explain why 

it was imposing a term of supervised release in contravention of U.S.S.G. § 5D1.1(c).” 

Appellant’s Br. at 8. We find that argument unpersuasive. 

We review a district court’s sentencing decisions for reasonableness under a deferential 

abuse-of-discretion standard. United States v. Cossey, 632 F.3d 82, 86 (2d Cir. 2011) (per 

curiam). We have found procedural error where “the district court miscalculates the Guidelines; 

treats them as mandatory; does not adequately explain the sentence imposed; does not properly 

consider the § 3553(a) factors; bases its sentence on clearly erroneous facts; or deviates from the 

Guidelines without explanation.” Id. (citing Gall v. United States, 552 U.S. 38, 51 (2007)). 

Where, as here, a defendant failed to raise the procedural objection at sentencing, we review for 
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plain error. 3 United States v. Caltabiano, 871 F.3d 210, 219 (2d Cir. 2017); see also United States 

v. Alvarado, 720 F.3d 153, 157 (2d Cir. 2013) (per curiam) (applying “[r]igorous plain error 

analysis” where a defendant failed to object to a district court’s failure to explain why supervised

release was warranted in light of Section 5D1.1(c)).

Contrary to Ovalle-Then’s assertion, the district court adequately explained why it imposed 

a term of supervised release. To be sure, Section 5D1.1(c) provides that “[t]he court ordinarily 

should not impose a term of supervised release in a case in which supervised release is not 

required by statute and the defendant is a deportable alien who likely will be deported after 

imprisonment.” The Guidelines Commentary for Section 5D1.1(c) further notes that supervised 

release is unnecessary unless a defendant legally returns to the United States because “[i]f such a 

defendant illegally returns to the United States, the need to afford adequate deterrence and protect 

the public ordinarily is adequately served by a new prosecution.” § 5D1.1 cmt. n. 5. Importantly, 

although that advisory guidance “ordinarily” applies, the Commentary further explains that “[t]he 

court should . . . consider imposing a term of supervised release on such a defendant if the court 

determines it would provide an added measure of deterrence and protection based on the facts and 

circumstances of a particular case.” Id.

Here, the district court noted that it had considered the Sentencing Guidelines and, utilizing 

the precise language contained in Section 5D1.1(c), specifically acknowledged that “a term of 

3

 Plain error exists “only where the appellant demonstrates that (1) there is an ‘error’; (2) the error is ‘clear 

or obvious, rather than subject to reasonable dispute’; (3) the error ‘affected the appellant’s substantial 

rights, which in the ordinary case means’ it ‘affected the outcome of the district court proceedings’; and (4) 

‘the error seriously affects the fairness, integrity or public reputation of judicial proceedings.’” United 

States v. Marcus, 560 U.S. 258, 262 (2010) (alteration adopted) (quoting Puckett v. United States, 556 U.S. 

129, 135 (2009)). 
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supervised release is not required by statute” and that Ovalle-Then was a “deportable alien who 

will likely be deported after imprisonment.” App’x at 89. The district court then explained that, 

notwithstanding Ovalle-Then’s deportability, it was imposing a term of supervised release “due 

to [his] criminal history and the fact that [he] returned to the United States while under a term of 

federal supervised release.”4 Id. That reasoning, which implicated the need to protect the public 

and to deter the defendant, was sufficient to explain the basis for the district court’s exercise of 

its discretion in imposing a term of supervised release despite Ovalle-Then’s anticipated 

deportation.5 See also Alvarado, 720 F.3d at 159 (holding that, even though “Section 5D1.1(c)

was not explicitly discussed at the sentencing hearing,” the district court’s explanation that 

defendant was particularly likely to re-enter the country unlawfully in the future was sufficient to 

support the imposition of a term of supervised release); United States v. Margiotti, 85 F.3d 100, 

105 (2d Cir. 1996) (per curiam) (noting that, in the context of sentencing, the “district court’s 

failure to expressly invoke [the specific Guidelines provision] or its accompanying commentary 

cannot itself suggest that the court’s approach was in error”). In short, we conclude that the 

district court did not err, much less plainly err, in imposing the term of supervised release.

4 In 2019, Ovalle-Then was convicted in federal court for conspiring to interfere with commerce by threats 

or violence, in violation of 18 U.S.C. § 1951, in connection with his participation in several armed robberies. 

He was sentenced principally to a forty-month term of imprisonment and a three-year term of supervised 

release. On August 17, 2021, he was removed to the Dominican Republic. On or about December 28, 

2021, while still on supervised release, he re-entered the United States. 

5 The district court also generally stated that it had considered the Section 3553(a) factors in imposing the 

sentence and, as part of its weighing of those factors, noted that it had “consider[ed] the fact that this was, 

this is a serious criminal record, conspiracy to commit a Hobbs Act robbery, and that [he] came back to the 

United States within four months after having been deported as a result of that conviction.” App’x at 88.
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* * *

We have considered Ovalle-Then’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