United States v. Kevin Jadiel Figueroa-Roman

Not for Publication in West's Federal Reporter
United States Court of Appeals
For the First Circuit
No. 20-1170
No. 25-1240
UNITED STATES
Appellee,
v.
KEVIN JADIEL FIGUEROA-ROMAN,
Defendant, Appellant.
APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF PUERTO RICO
[Hon. Francisco A. Besosa, U.S. District Judge]
Before
Barron, Chief Judge,
Hamilton* and Thompson, Circuit Judges.
Syrie D. Fried, with whom Good Schneider Cormier Fried &
Brooks was on brief, for appellant.
Maarja T. Luhtaru, Assistant United States Attorney, with
whom W. Stephen Muldrow, United States Attorney, and Juan Carlos
Reyes-Ramos, Assistant United States Attorney, Chief, Appellate
Division, were on brief, for appellee.
July 16, 2026
* Of the Seventh Circuit, sitting by designation.

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THOMPSON, Circuit Judge. Before us a second time, Kevin
Jadiel Figueroa-Roman appeals his 108-month sentence. He argues
his sentence should be vacated and his case remanded again because
the district court didn't have the authority to resentence him and
its sentencing explanation doesn't justify the 21-month upward
variance in his sentence. His first argument doesn't have merit,
but the second one does.
When we remanded this case for resentencing the first
time around, we explicitly asked the district court for further
clarification on certain ambiguous language in its initial
sentencing rationale so that we could discern the reasoning behind
the upward variance and aptly conduct appellate review. United
States v. Figueroa-Roman, No. 20-1170, 2024 WL 3458104, at *2 (1st
Cir. July 18, 2024). But the ambiguities remain and, consequently,
so does our inability to do what we do.
Because we write primarily for the parties (who are well
acquainted with the facts and proceedings in this case), we'll
recite only what's necessary to place the crucial issue into
perspective -- borrowing liberally from our earlier opinion.
Back in April 2019, Figueroa-Roman pleaded guilty to
four counts of aiding and abetting three associates in a string of
carjackings. Id. Pursuant to his plea agreement, Figueroa-Roman
asked for 63 months, while the government sought 70.5 months. Id.

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But to the district court, both sentencing recommendations were a
drop in the ocean. It sentenced Figueroa-Roman to 108 months of
imprisonment (an upward variance of 21 months outside of the
court-calculated guidelines range, also known as the "GSR," of 70
to 87 months) with each count to be served concurrently. Id.
Before handing down its sentencing decision, the district court
explained:
[T]he sentences recommended by the parties do
not reflect the seriousness of the offenses,
do not promote respect for the law, do not
protect the public from further crimes by
[Figueroa-Roman], and do not address the
issues of deterrence and punishment. The
[c]ourt has identified factors that warrant a
variant sentence above the guideline range
pursuant to the provisions of Title 18, U.S.
Code section 3553(a). The [c]ourt has
balanced [Figueroa-Roman]'s lack of a criminal
record, the pro-social support he enjoys from
his family, with the seriousness of the
offense, their violent nature, the
psychological impact caused to the victims,
and [Figueroa-Roman]'s association with
convicted felons when assessing
[Figueroa-Roman]'s risk to the community once
he is released.
Defense counsel did not object to the sentence at that
time.
On his first appeal to this court, and acknowledging he
was in plain-error territory because of his failure to preserve
below any claim of sentencing error, Figueroa-Roman took aim at
the district court's upward variance. He specifically emphasized

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the "association with convicted felons" comment in the district
court's sentencing explanation, arguing it was a factual error
unsupported by the record. Id. at *2.
The government asserted the "association with convicted
felons" comment went to assessing Figueroa-Roman's risk to the
community post-imprisonment and to describing his codefendant
associates' actions that led to felony convictions, rather than
their prior crimes. Id.
But in our scrutiny of Figueroa-Roman's claims during
appeal number one, we found the district court's language to be
ambiguous and concluded it was "unclear what the sentencing court
meant when it referred to Figueroa-Roman's 'association with
convicted felons.'" Id. We had the same luck -- and that's to
say none -- when we attempted to then inferentially understand the
district court's reasoning from the record because it could have
been interpreted in more ways than one. Id. at *3. So, we vacated
and remanded for the district court to address our specific
questions that went like this:
Are the "convicted felons" Figueroa-Roman's
carjacking codefendants? And was the court
saying those codefendants were felons at the
time of the offense? At the time of Figueroa-
Roman's sentencing? Post-release (and/or
likely to associate upon that release)? Was
the court referring to some other convicted
felons? At what point is Figueroa-Roman doing
the "associat[ing]" with these felons,
whomever they are? And what is the

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significance of any such "association" when
Figueroa-Roman had no criminal record at the
time of his offense and (unlike with some
repeat offenders, for instance) the record
reflects no prohibition on this
first-time-offender's association with
anyone?
Id. at *2 (alteration in original).
Following our remand, Figueroa-Roman stood before the
district court for resentencing having already served 68 months of
his 108-month sentence. Both his defense counsel and the
government advocated for a term of 70.5 months.1
Without acknowledging any parties' averments or
recommendations, the district court addressed, in a single
sentence, our remand for clarification on its "association with
convicted felons" comment:
As a clarification, the [c]ourt indicates that
contrary to what it stated when it originally
sentenced [Figueroa-Roman], he did not
associate with convicted felons. He
associated with his codefendants.
What came next felt a bit like déjà vu because it was
almost word-for-word what the district court said during
Figueroa-Roman's first sentencing hearing:
The [c]ourt finds that the sentences
recommended by both [Figueroa-Roman] and the
government do not reflect the seriousness of
1 At the resentencing hearing, Figueroa-Roman asked for "70
months[,] which was the same amount that the government requested
last time." We assume by this that he actually meant 70.5 months,
as that was the actual amount for which the government asked.

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[Figueroa-Romans]'s offenses, do not promote
respect for the law, do not protect the public
from additional crimes by [Figueroa-Roman],
and do not address the issues of deterrence
and punishment. The [c]ourt has identified
factors that warrant a variant sentence above
the guideline range pursuant to the provisions
of Title 18, U.S. Code section 3553(a). The
[c]ourt has balanced [Figueroa-Roman]'s lack
of a previous criminal record; the pro-social
support he enjoys from his family; and the
seriousness of these four offenses, their
violent nature and the psychological impact
that they caused the victims.
With that, the district court once again sentenced
Figueroa-Roman to 108-months' imprisonment as to each count to be
served concurrently. After the district court asked "[a]nything
else?," Figueroa-Roman's counsel said "[t]he defense would like to
place objections on the record as to the sentence issued. I think
that suffices directions of the First Circuit as to the basis for
an upward variance in this case." Defense counsel then lodged a
couple of objections accusing the court of improperly applying a
four-level sentencing enhancement for the weapons possession
charge and of disparately treating Figueroa-Roman in comparison to
his similarly situated codefendants. To this, the district court
simply responded:
Well, the court of appeals remanded this case
because the court, as I clarified today,
relied on [Figueroa-Roman]'s association with
convicted felons. It says: "[A]ccordingly, in
need of the aforementioned clarity to proceed,
the most prudent course here is for us to
vacate and remand so that the court can

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clarify what it meant by Figueroa-Roman's
association with convicted felons." I
clarified that by saying he did not associate
with convicted felons. He associated with his
codefendants. So your reconsideration is
denied.
Unsurprisingly, Figueroa-Roman appealed for the second
time. In response, we ordered the parties to submit supplemental
briefs to address the amended judgment.
And now Figueroa-Roman is back. He first (somewhat
strangely) contends that his resentencing fell outside of the
district court's authority because, according to him, our remand
was limited to the court's clarification of the "associated with
convicted felons" language. Thus, once the language was clarified,
he suggests, the district court had nothing else to do. The
government argues otherwise, contending that (1) he did not raise
such a jurisdictional argument before the district court and (2)
he affirmatively agreed to a resentencing
hearing -- Figueroa-Roman's counsel's opening exchange with the
court proves as much:
THE COURT: Mr. Rivera, is there anything
you'd like to say on behalf of
[Figueroa-Roman] before I pronounce sentence?
Mr. RIVERA-RODRIGUEZ: Yes, your Honor.
Essentially this case is here before this
[c]ourt for resentencing, your Honor . . . .
So I beg the [c]ourt to sentence him even to
70 months which was the same amount that the
government requested last time we came here
before the court.

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It's enough to say that defense counsel acknowledged
that the case was before the district court for resentencing and
thereafter asked the court to sentence Figueroa-Roman to "70
months." But to be clear, we specifically vacated Figueroa-Roman's
sentence and remanded the case so that the district court could
resentence Figueroa-Roman, clarify the "association with convicted
felons" language during resentencing, and articulate what role, if
any, this association played in the sentencing decision.
Figueroa-Roman, 2024 WL 3458104, at *2-3. In support, we cited
several cases that explained why the ambiguities necessitated our
remand for resentencing. Id. at *3; see also United States v.
Gilman, 478 F.3d 440, 447 (1st Cir. 2007) (holding that "we may
remand for resentencing when a court has provided no explanation
at the sentencing hearing"). So Figueroa-Roman's first argument
falls flat.
Figueroa-Roman next contends that his sentence was
procedurally unreasonable because the district court provided an
inadequate sentencing explanation to justify the 21-month upward
variance. In response, the government argues that Figueroa-Roman
supposedly waived this issue because his counsel stated that the
clarification imbedded within the district court's sentencing
explanation "suffices" our directions. Alternatively, the
government argues that the district court satisfied its remand

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obligations by clarifying that it meant to refer to
Figueroa-Roman's codefendants, rather than "convicted felons."
And from there the government repeats its original view that this
"association" went to assessing Figueroa-Roman's risk to the
community upon release because he was somehow more susceptible
than his codefendants to committing crimes. See Figueroa-Roman,
2024 WL 3458104, at *2.
First up is the waiver issue. Context shows that defense
counsel wasn't conceding that the district court's explanation
"suffice[d]" our directions. Rather, defense counsel was setting
up his firearm-enhancement and sentencing-disparity objections and
acknowledging that "plac[ing] objections on the
record . . . suffice[d]" for preservation purposes in line with
our precedent. So, from our vantage point this issue of the
district court's anemic sentencing explanation is not waived.
So let's turn to that explanation. And though the issue
isn't waived, we can't get much further today -- even on
plain-error review -- than we did in our first opinion on this
matter, and here's why.2 See Figueroa-Roman, 2024 WL 3458104, at
*1.
2 The government argues that Figueroa-Roman can't win anyhow
because (according to its view) he waived any explanation-based
objection by not tying his claim to the demanding plain-error
standard. But the premise of the government's theory is wrong.
He specifically writes that the district court's clarification

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It's a fixed requirement that a sentencing court must
provide an adequate enough sentencing explanation that allows "for
meaningful appellate review and to promote the perception of fair
sentencing." Gall v. United States, 552 U.S. 38, 50 (2007). And
the further away the district court strays from the sentencing
guidelines, the more particularized and compelling its sentencing
explanation must be. See United States v. Perez-Delgado, 99 F.4th
13, 25 (1st Cir. 2024) ("[T]he greater the variance, the greater
the explanation must be.").
The government doesn't dispute that the 21-month upward
variance is a significant one, requiring "a correspondingly cogent
explanation." United States v. Rivera-Berríos, 968 F.3d 130,
134-35 (1st Cir. 2020). In our first remand, we attempted to get
resulted in "a sentence record that contains less aggravating
information than what was before this [c]ourt at the time of [his]
initial brief." And he points out that we have "consistently found
that scanty sentencing explanations that are no more than rote
repetitions of language found in [18 U.S.C. § 3553(a)] do not pass
muster as being procedurally reasonable." We read these statements
as contending that the district court's explanation was both error
and an obvious one and, therefore, touching on plain error's first
two elements. See United States v. Montero-Montero, 817 F.3d 35,
37 (1st Cir. 2016) (citing United States v. Duarte, 246 F.3d 56,
60 (1st Cir. 2001)). And his reliance on United States v.
Muñoz-Fontanez -- a plain-error case noting that "the absence of
explanation" is prejudicial and "casts a shadow over the court's
reputation for fairness" when we can't discern the basis of an
upward variance, 61 F.4th 212, 214-15 (1st Cir. 2023) (citation
modified) - touches on plain error's last two elements. This is
enough -- even if just barely -- to avoid waiver. Cf. United
States v. Sevilla-Oyola, 770 F.3d 1, 14 (1st Cir. 2014).

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a detailed and reviewable sentencing explanation from the district
court by providing explicit instructions for it to explain the
significance and relevance of its original "association with
convicted felons" comment, see Figueroa-Roman, 2024 WL 3458104, at
*3, but what we got was a word substitution, "association with
codefendants." But the district court hasn't clarified how and
why Figueroa-Roman's "association" as a first-time offender
warranted the variance. See Rivera-Berríos, 968 F.3d at 135-36
(holding that the sentencing court's emphasis on a first-time
offender's association with his codefendants alone does not
support an upward variance). Nor did the district court explicitly
say, as the government asks us to posit, that this "association"
comment went to assessing Figueroa-Roman's risk to the community
post-imprisonment or likelihood of recidivism. That it simply
"misspoke" and said "felons" when it meant "codefendants" is not
a sufficient enough clarification. See United States v.
Colón-Cordero, 91 F.4th 41, 57-58 (1st Cir. 2024) (rejecting as an
argument that the sentencing court's mischaracterization of a fact
unsupported by the record was "an inartful slip of the tongue").
And when we scoured the record (including the statement of reasons)
to glean the district court's rationale on this factor, we again
found ourselves engaging in guesswork. See United States v.
Mantha, 944 F.3d 352, 357 (1st Cir. 2019) (vacating and remanding

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a sentence with an upwardly variant sentence because the record
didn't contain information by which we can infer the district
court's rationale). The lack of clarification coupled with the
conflicting plausible interpretations of the record have "a
material impact on our ability to undertake meaningful appellate
review." Figueroa-Roman, 2024 WL 3458104, at *3.
Accordingly, we vacate the sentence and remand this case
to the district court for expedited resentencing. On remand, the
district court is to reassess and explain, on the basis of the
existing record, Figueroa-Roman's "association" with his
codefendants and its significance, weight, and relevance to his
21-month upward variance.
Upon resentencing and consistent with our precedent, we
caution the district court to avoid certain pitfalls:
• boilerplate language that we've
repeatedly held as insufficient because it doesn't
account for the individual characteristics of the
offender or the offense, see United States v.
Flores-Nater, 62 F.4th 652, 656 (1st Cir. 2023); and
• factors already accounted for in the
GSR.3 See United States v. Valle-Colón, 21 F.4th 44,
3 For instance, even though the government conceded that
Figueroa-Roman didn't personally use a weapon (rather, it was he
who dropped a dime on the codefendant that used the weapon), the

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48 (1st Cir. 2021) ("In assessing a sentencing court's
explanation of an upwardly variant sentence, we must
'ask whether the [sentencing] court reasonably
explained the sentence in a manner that relies on
factors not adequately accounted for in the
[guidelines sentencing range].'" (alteration in
original) (quoting United States v. Díaz-Lugo, 963
F.3d 145, 156 (1st Cir. 2020))).
This panel retains jurisdiction over this matter.
- Dissenting Opinion Follows -
district court referenced Figueroa-Roman's use of a dangerous
weapon in its sentencing explanation after a four-level
enhancement was accounted for in the guidelines calculation (which
the district court recognized as correctly calculated) without
articulating why that factor was entitled to extra weight. See
Valle- Colón, 21 F.4th at 48.

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HAMILTON, Circuit Judge, dissenting. With respect, I
dissent from this second reversal and remand for a third
sentencing. I agree with much that the majority says, but I would
affirm because defendant Figueroa-Roman failed to preserve the
basis for the remand in both the district court and this court.
First, after our original remand, the defense never
objected in the district court that the judge's corrected
explanation was insufficient to explain the upward variance.
Counsel placed other specific objections on the record about
guideline issues. Counsel did not object, however, that the
judge's explanation of the upward variance was insufficient. The
only comment about the explanation is counsel's cryptic comment:
"I think that suffices directions of the First Circuit as to the
basis for an upward variance in this case." The most likely
reading of that comment is that the judge's explanation "sufficed"
to comply with the directions of the First Circuit. That's clear
waiver. It's certainly not an objection.
Federal Rule of Criminal Procedure 51(b) provides: "A
party may preserve a claim of error by informing the court—when
the court ruling is made or sought—of the action the party wishes
the court to take, or the party's objection to the court's action
and the grounds for that objection." Defense counsel had and took
the opportunity to raise other objections to the sentence. Counsel
simply did not object to the sufficiency of the explanation for

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the upward variance. He did not alert the district judge—who could
have corrected any arguable error on the spot—that he might need
to say more about his reasoning. A clear objection would have
invited further explanation and perhaps avoided this second
appeal.
Second, given the failure to object in the district
court, our appellate review is only for plain error, as my
colleagues agree. I understand this court's precedents to require
a defendant who seeks plain-error review to raise and address the
plain-error standard. This court routinely treats failure to do
so as waiver of the appellate argument. E.g., United States v.
Fargas-Reyes, 125 F.4th 264, 274 (1st Cir. 2025), citing United
States v. Cruz-Ramos, 987 F.3d 27, 40 (1st Cir. 2021) (defendant
waived appellate claim where "his brief fails to even mention plain
error, let alone argue for its application here"); accord, e.g.,
United States v. Velázquez-Aponte, 940 F.3d 785, 800 (1st Cir.
2019) (finding waiver based on failure to make plain-error
argument); United States v. Severino-Pacheco, 911 F.3d 14, 20 (1st
Cir. 2018) (same); United States v. Pabon, 819 F.3d 26, 33-34 (1st
Cir. 2016) (same).
In his first appeal, this defendant was represented by
the same attorney as in this appeal, and he satisfied that
requirement. He quoted the canonical plain-error standard and
argued how it should apply. No. 20-1170, Appellant's Br. at 8 &

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18–19. In this appeal, however, in the words of Cruz-Ramos, the
defense brief "fails to even mention plain error, let alone argue
for its application here." My colleagues have chosen to overlook
those failures here. Ante at 10 n.2. They base this reading on
the defendant's argument that the district court erred on the
merits (though such an argument will always be present in such
cases), and his citation to a case that itself applied plain-error
review. In light of this circuit's routine practices in plain-
error cases, that explanation does not convincingly make up for
the failure simply to ask for plain-error review, let alone for
the absence of the four-element standard and a coherent argument
that the four elements are satisfied.
So the case will return again to Judge Besosa. I do not
know if I would have imposed the same sentence, in his shoes. On
the merits, this is a tough case to sentence. There are
substantial aggravating factors and mitigating factors. But the
discretion and the human element in sentencing in this case belong
to the district court. The defendant's participation in five armed
carjackings in just a week, the violence of the crimes, and the
profound and lasting psychological injuries to at least some of
the victims can reasonably support the upward variance here. This
defendant is not a victim of the criminal justice system or an
unreasonable sentence.

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