United States v. Rivera

1
22-2081
United States v. Rivera
United States Court of Appeals
For the Second Circuit
August Term 2023
Argued: February 15, 2024
Decided: August 21, 2024
No. 22-2081
U NITED S TATES OF AMERICA
Appellee,
v.
V ICTOR R IVERA, AKA S EALED D EFENDANT 1,
Defendant-Appellant,
MICHOLS PENA, AKA S EALED D EFENDANT 2,
JOHAN A RAUJO
Defendants.
Appeal from the United States District Court
for the Southern District of New York

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No. 20-cr-600, Alvin K. Hellerstein, Judge.
Before: Jacobs, Chin, and Nathan, Circuit Judges.
Defendant-Appellant Victor Rivera appeals from a judgment of
the United States District Court for the Southern District of New York
(Hellerstein, J.) after pleading guilty pursuant to a plea agreement to
participating in a Hobbs Act robbery conspiracy. On appeal, Rivera
argues (1) that the Government breached the terms of the plea
agreement, (2) that his sentence is procedurally and substantively
unreasonable, and (3) that this case should be remanded for
resentencing in light of an amendment to the Guidelines after his
sentencing. We conclude that none of Rivera’s challenges prevail.
Notably, although we find that the Government breached the
plea agreement when it sought a higher Guidelines range than the
one stipulated to in Rivera’s plea agreement based on criminal history
available to it at the time of the plea, we conclude that this error does
not amount to a “plain” error under the applicable standard.
Accordingly, we AFFIRM.
A NNA MARGARET S KOTKO,
Skotko Law PLLC, New York,
NY, for Defendant-Appellant.
A NDREW K. CHAN (Mathew
Andrews, Danielle Renee
Sassoon, Thomas John Wright,
Alison Moe, on the brief),
Assistant United States
Attorneys, for Damian
Williams, United States

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Attorney for the Southern
District of New York, New
York, NY, for Appellee.
NATHAN, Circuit Judge:
The Supreme Court has long acknowledged the “essential” role
that plea bargaining plays in “the administration of justice.”
Santobello v. New York, 404 U.S. 257, 260 (1971). Our Court has also
encouraged prosecutors to inform defendants of their likely sentence
range under the federal Sentencing Guidelines to enable defendants
to more “fully appreciate the consequences of their pleas.” United
States v. Pimentel, 932 F.2d 1029, 1032 (2d Cir. 1991). It is therefore
unsurprising that plea agreements today are commonly drafted to
include stipulated sentence ranges that the parties agree not to
dispute at sentencing. While stipulating to certain sentence ranges in
a plea agreement can reduce “claims of unfair surprise” from
defendants, United States v. Wilson, 920 F.3d 155, 163 (2d Cir. 2019)
(quotation marks omitted), this is true only if the government actually
keeps its promises.
The question in this appeal is whether the government breaches
a plea agreement when it stipulates to a sentence range based on
information “available” to it, then advocates for a substantially higher
sentence based on criminal history information that it could have
readily obtained. We hold that it does, though the error is
insufficiently “plain” to warrant resentencing in the present case.
Furthermore, we reject Rivera’s claim that the Government

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breached his plea agreement by describing him as a leader. We
likewise conclude that Rivera’s procedural and substantive
challenges to his sentence fail. Finally, we reject Rivera’s request to
remand this case for resentencing due to a recent amendment to the
Sentencing Guidelines. Accordingly, we AFFIRM the judgment of
the district court.
BACKGROUND
Between October 2019 and November 2020, Defendant-
Appellant Victor Rivera participated in a robbery crew responsible
for over a dozen robberies of jewelers and luxury watch owners. The
robbery crew identified their potential victims on social media, before
surveilling and ambushing them outside of their homes, often at
gunpoint. Rivera was arrested, and a grand jury returned an 18-count
indictment.
Pursuant to a plea agreement prepared by the U.S. Attorney’s
Office for the Southern District of New York, Rivera pled guilty to one
count of participating in a Hobbs Act robbery conspiracy in violation
of 18 U.S.C. § 1951. Like many other plea agreements executed by the
U.S. Attorney’s Office, Rivera’s agreement contained a stipulated
Guidelines range that the parties agreed not to contest at sentencing.
The agreement stated as follows: “Based upon the information
now available to this Office (including representations by the
defense), the defendant has three criminal history points.” App’x at
44. This placed Rivera into Criminal History Category II. The
agreement also calculated a total offense level of 34, and as relevant
here, imposed no role enhancement under U.S.S.G. § 3B1.1.

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Together, these calculations resulted in a “Stipulated Guidelines
Range” of 168 to 210 months’ imprisonment. Id. at 45.
Rivera and the U.S. Attorney’s Office agreed that “neither party
[would] seek any departure or adjustment,” nor “in any way suggest
that” the sentencing court consider a departure or adjustment from
the stipulated guidelines range, unless permitted by the agreement.
Id. The parties were permitted to seek an adjustment in certain
circumstances—for example, the parties could seek a variance based
upon the sentencing factors under 18 U.S.C. § 3553(a), or “based upon
new information that the defendant’s criminal history category [was]
different from that set forth” in the agreement. Id.
On April 8, 2022, the Probation Office issued its final
Presentence Investigation Report (PSR). The PSR included three
convictions Rivera obtained in Puerto Rico during 2012 and 2013 that
were not accounted for in the plea agreement. In light of these
additional convictions, Probation calculated ten criminal history
points, significantly higher than the three criminal history points
stipulated to in the plea agreement. This placed Rivera in Criminal
History Category V. Probation calculated the applicable Guidelines
sentence to be the statutory maximum of 240 months1 but
recommended a sentence of only 160 months.
In its sentencing submission, the Government agreed with the
PSR’s criminal history calculation and argued for a revised
Guidelines range of 235 to 240 months’ imprisonment, capped by the
1 Probation also calculated a higher total offense level of 35 as opposed to the total
offense level of 34 calculated in the plea agreement. The government did not,
however, rely on this revised total offense level for its sentencing submission.

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statutory maximum of 240 months. The Government explained that
it was advocating for a higher applicable Guidelines range than the
stipulated range of 168 to 210 months because of Rivera’s “extensive
criminal history in Puerto Rico,” which the Government “was
unaware of . . . at the time of the plea agreement[.]” App’x at 75.
At sentencing, defense counsel agreed that the applicable
Guidelines range was 235 to 240 months. However, he also explained
that he had assumed that the Government “reviewed a rap sheet”
prior to preparing the plea agreement and thus also “assumed when
[Rivera] entered into these plea negotiations that the sentencing
guideline range was what the [U.S. Attorney’s Office] represented it
to be.” App’x at 84–85. Despite this, the district court agreed that the
applicable Guidelines range was 235 to 240 months.
Rivera requested a 96-month term of imprisonment, arguing
that a variance was warranted under the § 3553(a) factors in light of
his difficult childhood and history of serious mental illness. The
Government advocated for a sentence within the applicable
Guidelines range. The district court agreed with the Government and
sentenced Rivera to 235 months’ imprisonment, to be followed by
three years of supervised release.
DISCUSSION
I. Breach of Rivera’s Plea Agreement
On appeal, Rivera argues that the Government breached the
terms of his plea agreement in two respects. First, he argues that the
Government breached the agreement by relying on his Puerto Rico
convictions to advocate for a higher Guidelines range at sentencing.
Second, he argues that the Government breached the agreement by

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describing him as a leader in its sentencing statements. Although we
agree that the Government’s request for a higher sentence range
violated the plea agreement, we nonetheless reject both arguments
under the plain error standard.
“We review a plea agreement in accordance with principles of
contract law and look to what the parties reasonably understood to
be the terms of the agreement to determine whether a breach has
occurred.” United States v. Sealed Defendant One, 49 F.4th 690, 696 (2d
Cir. 2022) (quotation marks omitted). “We do so by looking to the
precise terms of the plea agreements and to the parties’ behavior.”
United States v. Helm, 58 F.4th 75, 83 (2d Cir. 2023) (quotation marks
omitted).
Ordinarily, the government enjoys disproportionate
bargaining power in plea agreement negotiations. See United States v.
Riera, 298 F.3d 128, 133 (2d Cir. 2002). We accordingly “construe plea
agreements strictly against the government and do not hesitate to
scrutinize the government’s conduct to ensure that it comports with
the highest standard of fairness.” United States v. Wilson, 920 F.3d 155,
162 (2d Cir. 2019) (quotation marks omitted).
A. New Information
Rivera argues first that the Government breached his plea
agreement by relying on his 2012 and 2013 Puerto Rico convictions to
advocate for a higher Guidelines range than the range stipulated to in
the agreement.
An argument that the government breached a plea agreement
is reviewed for plain error if the defendant failed to object in the
district court. United States v. MacPherson, 590 F.3d 215, 218 (2d Cir.

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2009). Rivera maintains that his attorney’s objections at sentencing
were adequate to preserve this argument. While a defendant need
not object “on the specific ground that the government breached the
plea agreement to preserve such a claim for appellate review, the
defendant must object in a manner sufficient to apprise the court and
opposing counsel of the nature of [his] claims regarding the
impropriety of the [g]overnment’s change in position.” United States
v. Taylor, 961 F.3d 68, 81 n.12 (2d Cir. 2020) (quotation marks omitted).
Rivera’s objections fell short of this requirement. Although
defense counsel explained at sentencing that Rivera expected only the
criminal history contained in his plea agreement to be considered for
his sentence calculation, he never specifically contended that any
provision of the plea agreement was breached. To the contrary,
defense counsel “agree[d] with” the district court in the calculation of
the revised Guidelines range. App’x at 84. Rivera’s general
frustration that the applicable Guidelines range was higher than
anticipated was, at best, an argument about fairness. None of his
statements made at sentencing indicate he was alleging that the
Government’s advocacy amounted to a breach of Rivera’s plea
agreement. Accordingly, these objections were insufficient to apprise
the Government and sentencing court of a legal claim for breach of
the plea agreement.
We thus review this breach claim for plain error. “To establish
plain error, a defendant must demonstrate: (1) error, (2) that is plain,
and (3) that affects substantial rights.” Taylor, 961 F.3d at 81
(quotation marks omitted). If all three requirements are satisfied,
then we must also consider whether the error “seriously affects the

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fairness, integrity, or public reputation of judicial proceedings.”
United States v. Bleau, 930 F.3d 35, 39 (2d Cir. 2019).
In this case, we conclude that the Government broke its
promise to abide by the stipulated Guidelines range at sentencing and
therefore breached the plea agreement. Based on the terms of that
agreement, Rivera reasonably expected that the Government would
not rely on criminal history information “available” to it at the time
of the plea to request a higher Guidelines range. However, the
Government did exactly that when it relied on unsealed convictions
that it was put on notice of and could have readily obtained at the
time of the plea. The Government’s reliance on this information to
advocate for a higher Guidelines range was a violation of Rivera’s
reasonable expectations.
We start with the relevant terms of the plea agreement. There
is no dispute that the plea agreement prohibited the Government
from seeking an adjustment from the stipulated range of 168 to 210
months unless permitted by the agreement. Nor is there any dispute
that the agreement allowed the Government to advocate for an
adjusted Guidelines range based on “new information” about
Rivera’s criminal history. App’x at 45. The sole dispute here is
whether Rivera’s 2012 and 2013 Puerto Rico convictions constitute
“new information” under the plea agreement.
We look to the “precise terms” of the plea agreement to discern
“what the reasonable understanding and expectations of the
defendant were as to the sentence for which he had bargained.”
Wilson, 920 F.3d at 163 (cleaned up). Here, the terms of the agreement
provided that the parties may “seek an appropriately adjusted

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Guidelines range . . . based upon new information that the
defendant’s criminal history category is different from that set forth”
in the agreement. App’x at 45. What counts as “new information,”
then, depends on what information was already accounted for in
calculating the “criminal history category . . . set forth” in the
agreement. Cf. United States v. Palladino, 347 F.3d 29, 34 (2d Cir. 2003);
Wilson, 920 F.3d at 164. And the agreement provided that the criminal
history category was calculated “[b]ased upon the information now
available” to the U.S. Attorney’s Office. App’x at 44 (emphasis added).
Read together, these provisions indicate that any criminal history
information “available” to the U.S. Attorney’s Office does not count
as “new information” within the terms of the plea agreement. In other
words, the Government agreed not to advocate for a higher sentence
except in reliance on information that was not “available.”
Since the plea agreement does not define “available,” we look
to the ordinary meaning of the term. See Dish Network Corp. v. Ace Am.
Ins. Co., 21 F.4th 207, 211 (2d Cir. 2021). As the Supreme Court has
explained, “the ordinary meaning of the word ‘available’ is ”‘capable
of use for the accomplishment of a purpose,” and that which ‘is
accessible or may be obtained.’” Ross v. Blake, 578 U.S. 632, 642 (2016)
(quoting Booth v. Churner, 532 U.S. 731, 737–38 (2001)); see also
Merriam-Webster’s Unabridged Dictionary (3d ed. 1993) (defining
“available” as “accessible or may be obtained”); Cambridge
Dictionary (2d ed. 2008) (defining “available” as “able to be obtained,
used, or reached”); The American Heritage Dictionary (5th ed. 2011)
(defining “available” as “[c]apable of being gotten; obtainable”).
Therefore, the Government may abandon its promise to recommend

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the stipulated sentence range based on “new information” about
Rivera’s criminal history only if such information was not
“accessible” and could not have been “obtained” by the Government
at the time of the plea.
Our interpretation charts a middle ground between the parties’
clashing readings of what counts as “new information.” In its
briefing, the Government argued that any information that the
Government did not know about during the plea is “new
information.” At oral argument, the Government went further and
suggested that the “new information” provision was a “carveout”
provision broadly authorizing reliance on any criminal history
information not accounted for in the agreement.
But these readings fail to capture the scope of information
“available” to the Government at the time of the plea. Plea
agreements are reviewed “in accordance with principles of contract
law,” Wilson, 920 F.3d at 162, which “require that all provisions of a
contract be read together as a harmonious whole,” Kinek v. Paramount
Commc'ns, Inc., 22 F.3d 503, 509 (2d Cir. 1994). As we explained above,
the scope of “new information” cannot be defined in isolation. It must
be read alongside the provision specifying what information was
already accounted for in calculating the stipulated sentencing range.
That range was based on information “now available” to the U.S.
Attorney’s Office, not information “known to” the U.S. Attorney’s
Office, nor information “existing as of today.”
For this reason, the Government’s reliance on various cases
from our Circuit is unavailing. Those decisions provide only limited
guidance as they interpreted plea agreements containing different

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language. United States v. Soto, for instance, involved a plea
agreement containing stipulations based on “information known to
the government.” 706 F. App’x 689, 691 (2d Cir. 2009) (summary
order) (emphasis added). Similarly, United States v. Santana involved
a plea agreement reserving the government’s right to modify its
position “if it subsequently received previously unknown
information.” 112 F. App’x 787, 789 (2d Cir. 2004) (summary order)
(emphasis added).2 In these cited cases, the government reserved a
more expansive right to change its position as compared to what the
government bargained for in the present case. As this Court has
explained, inclusion of “[t]he words, ‘based on information known to
the government,’” communicates “the government’s freedom to
advocate for a higher guideline range when its change of position is
based on its subsequent acquisition of aggravating information.”
United States v. Habbas, 527 F.3d 266, 272 n.1 (2d Cir. 2008). But here,
the Government reserved its right to change its position based only
on information not available to it at the time of the plea. These terms
convey different meanings because, put simply, information can be
unknown to the government yet readily available, accessible, and
obtainable. See Merriam-Webster’s Unabridged Dictionary (3d ed.
1993) (defining “know” as “perceive directly” and “have direct
unambiguous cognition of”).
A hypothetical posed at oral argument illustrates the point:
2 The government also relies on United States v. Johnson, 93 F.4th 605, 617 (2d Cir.
2024). But Johnson concerned the government’s promise not to prosecute any other
offenses not known to it at the time of the plea agreement. Because Rivera’s plea
agreement does not contain a similar promise, Johnson offers little insight on how
to interpret the terms disputed by the parties here.

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Imagine the U.S. Attorney’s Office simply misplaced a page of the rap
sheet containing a defendant’s past convictions. It proceeds to
prepare a plea agreement that fails to account for those convictions.
Under these circumstances, the government may have lacked
knowledge of the past convictions, but the information at issue was
nevertheless clearly available. Asked whether the “carveout”
provision would apply in such a case, the Government still answered
in the affirmative based on the Government’s lack of knowledge. But
traditional contract principles require us to give the precise terms in
a plea agreement their plain and ordinary meaning. See Dish Network
Corp., 21 F.4th at 211. Under this principle, we may not read the
words “information now available” to mean “information now
known.”
Nor can we adopt Rivera’s preferred reading, which equates
“new information” with information that “recently c[a]me into
existence.” Appellant’s Br. at 19. On that interpretation, the plea
agreement would suggest that the Government, in reaching the
stipulated Guidelines range, has accounted for all criminal history
information in existence at the time of the plea. But that reading
similarly goes too far and does not comport with a defendant’s
“reasonable understanding and expectations” based on the ordinary
meaning of the agreement terms. Wilson, 920 F.3d at 163. That is
because there may well be cases in which criminal history information
exists but is nevertheless not “available” to the government in the
ordinary sense of the term because it may be infeasible for the
government to obtain certain information. In a different context, we
have explained that something can be “technically available” but

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nonetheless not “available” under the plain meaning of the term if it
is too confusing or opaque to reasonably pursue. See Williams v. Corr.
Officer Priatno, 829 F.3d 118, 126 (2d Cir. 2016) (discussing the
meaning of “available” administrative remedies under the Prison
Litigation Reform Act). Here too, information can be technically
available yet not considered “available” to the government if it is not
reasonably obtainable. For example, a defendant’s criminal history
information might not be “available” where the government has no
notice of its existence or simply lacks the means to obtain it. In those
circumstances, a defendant cannot reasonably expect the government
to have accounted for such information in calculating a stipulated
sentence based on information “available” to it. Accordingly, we
conclude that, under the plain terms of the plea agreement, a criminal
defendant reasonably expects and understands that the government
would not rely on criminal history information available to the U.S.
Attorney’s Office at the time of the plea as a basis to abandon the
stipulated Guidelines range.
Under our reading of the plea agreement, then, the question in
this case is whether the Government has shown that the criminal
history information justifying an adjustment was previously
unavailable (i.e., not reasonably obtainable at the time of the plea).
The answer is no. Not only has the Government failed to muster any
explanation for its prior inability to account for Rivera’s Puerto Rico
convictions, but the Government conceded during oral argument
that, had it tried, it could have obtained the relevant information. So
while the U.S. Attorney’s Office did not learn about Rivera’s Puerto
Rico convictions until it reviewed the PSR, we conclude that such

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information was nonetheless “available,” because it was reasonably
obtainable by the U.S. Attorney's Office at the time of the plea. We
reach this conclusion for two related reasons.
First, the Government was reasonably expected to investigate
whether Rivera had Puerto Rico convictions because it was put on
notice of the possibility of such convictions by Rivera’s rap sheet. At
oral argument, the Government explained that it used a rap sheet to
prepare the plea agreement. This rap sheet contained Rivera’s past
arrests in Puerto Rico but did not mention whether the arrests led to
convictions. The information about these arrests, however, should
have prompted further investigation on the Government’s part into
whether the arrests resulted in convictions. That Probation,
presumably relying on the same rap sheet, chose to conduct further
due diligence into Rivera’s Puerto Rico criminal history in preparing
the PSR confirms that the rap sheet signaled the possibility that Rivera
had Puerto Rico convictions.
Second, and relatedly, the information at issue was readily
obtainable by the Government upon investigation. The Puerto Rico
convictions were unsealed and thus available in public records. At
oral argument, the Government conceded that it could have obtained
this criminal history information by simply contacting the relevant
Puerto Rico courthouses. The Government offers no reason for its
failure to account for these unsealed convictions in the plea
agreement. It is inexplicable, then, why the Government chose not to
obtain this information after it was put on notice from the rap sheet
of Rivera’s prior arrests in Puerto Rico.
Finally, even if whether Rivera’s Puerto Rico convictions were

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“available” to the government was ambiguous, that would not aid the
Government’s case because we are obligated to construe all
ambiguities strictly against the government. See Wilson, 920 F.3d at
162.
We thus conclude that Rivera’s 2012 and 2013 Puerto Rico
convictions was information “available” to the Government at the
time of the plea and that the Government breached the plea
agreement by relying on these convictions for its advocacy at
sentencing.
In finding breach in today’s case, we do not suggest that the
Government acted in bad faith. But even if other factors such as high
workload could explain the Government’s failure to obtain Rivera’s
readily available relevant criminal history, they cannot excuse it.
Santobello v. New York, 404 U.S. 257, 260, 262 (1971) (“That the breach
of agreement was inadvertent does not lessen its impact.”). We have,
of course, acknowledged that the government is not immune to
mistakes or oversights when preparing plea agreements. See United
States v. Habbas, 527 F.3d 266, 272 n.1 (2d Cir. 2008). But where the
government has chosen to bind itself to advocating for a stipulated
Guidelines range, it must hold itself to that promise. A plea
agreement, like any contract, binds one party to an obligation in
exchange for a benefit. In exchange for the government’s promise to
abide by the stipulated sentence range, Rivera surrendered his
constitutional right to a trial and relieved the government of its
burden to prove his guilt beyond a reasonable doubt.
Both parties bound themselves to their respective
commitments. Keeping its promise does not prevent the government

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from carrying out its responsibilities to the sentencing court, because
the government remains free to honestly answer any of the court’s
inquiries. But the distinction between answering inquiries and
affirmative advocacy is one that matters. The government plays an
outsized, and sometimes even a decisive, role at sentencing. See
United States v. Lawlor, 168 F.3d 633, 637 (2d Cir. 1999). It is therefore
imperative that the government be far more careful in fulfilling its
responsibilities where plea agreements are involved.
In short, the goals of plea bargaining are best served when the
defendant’s criminal history is accurately reflected in the plea
agreement. More information about the consequences of pleading
guilty translates into a more rational and informed decision about
whether to plead guilty at the expense of exercising one’s
constitutional right to a trial. Following that logic, our Court has
repeatedly “recognized the desirability of having each defendant, at
the time of tendering a guilty plea, fully cognizant of his likely
sentence under the Sentencing Guidelines.” See Pimentel, 932 F.2d at
1034 (cleaned up). This is especially imperative when over 97% of
defendants in federal cases plead guilty. U.S. SENTENCING
COMM’N, Annual Report 16 (2023),
https://www.ussc.gov/sites/default/files/pdf/research-and-
publications/annual-reports-and-sourcebooks/2023/2023-Annual-
Report.pdf [https://perma.cc/8MZG-U5BA]; see also Lafler v. Cooper,
566 U.S. 156, 170 (2012) (“[C]riminal justice today is for the most part
a system of pleas, not a system of trials.”). In this case, we conclude
that the Government’s efforts fell short.
Our finding that the Government breached, however, does not

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end the analysis. To constitute plain error, a resulting error must also
be plain and affect substantial rights. In this case, we ultimately
conclude that the Government’s breach was not sufficiently “clear” or
“obvious” as to be “plain” error. United States v. Aybar-Peguero, 72
F.4th 478, 487 (2d Cir. 2023). Such an “error must be so plain that ‘the
trial judge and prosecutor were derelict in countenancing it, even
absent the defendant’s timely assistance in detecting it.’” United States
v. Villafuerte, 502 F.3d 204, 209 (2d Cir. 2007) (quoting United States v.
Frady, 456 U.S. 152, 163 (1982)). But prior to today, we lacked Circuit
guidance on how to read the term “available” used in Rivera’s plea
agreement to define the scope of the government’s commitments. Cf.
Puckett v. United States, 556 U.S. 129, 143 (2009) (“Plea agreements are
not always models of draftsmanship, so the scope of the
Government’s commitments will on occasion be open to doubt.”). It
was not obvious to the trial judge, then, that the terms of the plea
agreement prohibited the Government’s reliance on Rivera’s Puerto
Rico convictions to advocate for a higher Guidelines range. Absent
an objection by the defendant, we do not think the sentencing court
had reason to believe that a breach occurred, much less that it was
derelict in failing to remedy the breach. Thus, we conclude that any
error was not plain.3
Therefore, while the Government committed a breach, Rivera
does not satisfy the requirements of plain error review.
B. Leadership Role
3 Because we conclude that the error was not plain, we need not address whether
it affected Rivera’s substantial rights.

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Rivera argues next that the Government breached his plea
agreement by describing him as a leader in the conspiracy when the
plea agreement contained no Guidelines enhancement for a
leadership role under U.S.S.G. § 3B1.1. Because Rivera did not raise
this objection below, we review this argument for plain error as well.
See United States v. Sealed Defendant One, 49 F.4th 690, 696 (2d Cir.
2022).
We conclude that the Government’s statement in its sentencing
submission regarding Rivera’s leadership role in the conspiracy was
not error, much less plain error. In using those descriptors, the
Government in no way suggested that any role enhancement under
U.S.S.G. § 3B1.1 was warranted. Instead, the express terms of Rivera’s
plea agreement allowed the Government to “present” to the
sentencing court “any facts relevant to sentencing.” App’x at 45. And
among the § 3553(a) sentencing factors are “the nature and
circumstances of the offense,” along with “the need for the sentence
imposed . . . to reflect the seriousness of the offense, to promote
respect for the law, and to provide just punishment for the offense.”
18 U.S.C. § 3553(a)(1), (2)(A). So, even if the facts surrounding
Rivera’s role in the conspiracy did not warrant a Guidelines
enhancement under U.S.S.G. § 3B1.1, those facts remain relevant to
the district court’s application of the sentencing factors. Accordingly,
we find no error.4
4 There is some tension, at least in our summary orders, as to whether the
Government may highlight a criminal defendant’s leadership role without
simultaneously seeking a leadership enhancement under U.S.S.G. § 3B1.1(a).
Compare United States v. Tokhtakhounov, 607 F. App’x 8, 11 (2d Cir. 2015) (summary

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Accordingly, we find Rivera’s breach arguments meritless.
II. Sentencing Challenges
Rivera next challenges his sentence as procedurally and
substantively unreasonable. It is not.
We begin with Rivera’s argument that his sentence was
procedurally unreasonable because the district court misunderstood
its discretion to apply a sentence below the applicable Guidelines
range. Applying a plain error standard of review, because Rivera did
not raise this argument below, see United States v. Verkhoglyad, 516 F.3d
122, 128 (2d Cir. 2008), we disagree.
“A sentence is procedurally unreasonable when: the district
court (1) fails to calculate the Guidelines range; (2) is mistaken in the
Guidelines calculation; (3) treats the Guidelines as mandatory; (4)
does not give proper consideration to the § 3553(a) factors; (5) makes
clearly erroneous factual findings; (6) does not adequately explain the
sentence imposed; or (7) deviates from the Guidelines range without
explanation.” United States v. Diamreyan, 684 F.3d 305, 308 (2d Cir.
2012) (quotation marks omitted).
Rivera’s procedural unreasonableness challenge rests on his
assertion that the record lacks an affirmative indication that the
district court understood its authority to depart from the applicable
Guidelines range. But in the absence of record evidence suggesting
order) (finding no breach of the plea agreement when the Government
characterized the defendants as “leaders of the criminal enterprise”), with United
States v. Robinson, 634 F. App’x 47, 50 (2d Cir. 2016) (summary order) (finding a
breach of the plea agreement when the Government described the defendant as a
“managing member” of the conspiracy). But even if we assume that the
Government erred, Rivera cannot prevail under the plain-error standard.

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otherwise, we “presume that the district court understands the extent
of its sentencing authority.” United States v. Silleg, 311 F.3d 557, 561
(2d Cir. 2002). And that is the case here; Rivera has failed to put forth
any record evidence suggesting that the sentencing judge
misunderstood his authority to impose a below-Guidelines sentence.
We thus conclude that Rivera’s sentence is procedurally reasonable.
Having found no procedural error, we next consider Rivera’s
substantive reasonableness challenge. See Gall v. United States, 552
U.S. 38, 51 (2007). Even assuming review under an abuse-of-
discretion standard, see United States v. Thavaraja, 740 F.3d 253, 258 n.4
(2d Cir. 2014), we conclude that Rivera’s sentence is substantively
reasonable as well.
“A sentence is substantively unreasonable when it cannot be
located within the range of permissible decisions, because it is
shockingly high, shockingly low, or otherwise unsupportable as a
matter of law.” United States v. Osuba, 67 F.4th 56, 68 (2d Cir. 2023)
(quotation marks omitted). “A sentencing judge has very wide
latitude to decide the proper degree of punishment for an individual
offender and a particular crime.” United States v. Cavera, 550 F.3d 180,
188 (2d Cir. 2008) (en banc).
On appeal, Rivera argues that the district court’s 235 month-
sentence was substantively unreasonable given various mitigating
factors, an overstated criminal history, and disparity as compared to
the sentence recommended for one of the codefendants. But the
record reflects that the district court acknowledged the mitigating
factors in its sentencing, expressly taking into account Rivera’s mental
health history and difficult upbringing. The sentencing judge also

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noted that despite his difficult circumstances, Rivera failed to
acknowledge the harm caused by his crimes, including the gunshot
injury suffered by one victim. And the record explains the disparity
in the recommended sentence, as the codefendant had no prior
criminal history, had participated in only two of the eleven robberies,
had not carried a firearm, and had not injured any victims.
Rivera’s disagreement with the district court’s weighing of
these factors alone does not render his sentence substantively
unreasonable. We have explained that “[t]he particular weight to be
afforded aggravating and mitigating factors is a matter firmly
committed to the discretion of the sentencing judge, with appellate
courts seeking to ensure only that a factor can bear the weight
assigned it under the totality of circumstances in the case.” United
States v. Alcius, 952 F.3d 83, 89 (2d Cir. 2020) (alternation in original)
(quotation marks omitted). And considering the totality of
circumstances in this case, we find that Rivera’s 235-month
sentence—which we note falls at the bottom of the applicable
Guidelines range—can surely “be located within the range of
permissible decisions.” United States v. Degroate, 940 F.3d 167, 174 (2d
Cir. 2019) (quotation marks omitted).
We accordingly conclude that Rivera’s sentence is both
procedurally and substantively reasonable.
III. U.S.S.G. § 4A1.1 Amendment
Lastly, we reject Rivera’s request to remand this case for
resentencing due to a recent amendment to the Sentencing
Guidelines, which would reduce the offense level calculation for
certain defendants under U.S.S.G. § 4A1.1. Although we may apply

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post-sentence Guidelines amendments that “clarify their
application,” “we may not, in the first instance, apply post-sentence
amendments that embody a substantive change to the Guidelines.”
United States v. Jesurum, 819 F.3d 667, 672 (2d Cir. 2016) (quotation
marks omitted). Here, however, the § 4A1.1 amendment effects a
substantive change to the Guidelines and thus does more than merely
clarify the applicability of § 4A1.1. Specifically, the amendment (1)
reduces the upward adjustment received by offenders who
committed the instant offense while under any criminal sentence and
(2) limits this adjustment to defendants with seven or more criminal
history points. See U.S. Sent’g Comm’n, Sentencing Guidelines, 88
Fed. Reg. 28,254, 28,273 (effective Nov. 1, 2023); U.S.S.G. § 4A1.1(e).
Any argument seeking to retroactively reduce Rivera’s sentence on
this ground, however, must be raised before the district court in the
first instance.5 We therefore deny Rivera’s resentencing request.
CONCLUSION
Accordingly, the judgment of the United States District Court
for the Southern District of New York is AFFIRMED.
5 Congress has indicated that this Guidelines amendment may be applied
retroactively through a sentence reduction motion under 18 U.S.C. § 3582(c)(2).
See U.S.S.G. 1B1.10.

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