United States v. Boria

24-1871
United States v. Boria
United States Court of Appeals
for the Second Circuit
August Term 2025
Argued: October 24, 2025
Decided: February 4, 2026
No. 24-1871
UNITED S TATES OF AMERICA,
Appellee,
v.
S TEVE B ORIA, AKA C HROME ,
Defendant-Appellant.*
Appeal from the United States District Court
for the Southern District of New York
No. 17-cr-00142
Ronnie Abrams, Judge.
Before: KEARSE , L OHIER , and PARK , Circuit Judges.
* The Clerk of the Court is respectfully directed to amend the caption
as set forth above.

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Steve Boria took medications for sleeping problems and bipolar
disorder the night before he pleaded guilty to conspiring to distribute
cocaine and possessing a firearm. During the plea colloquy, the
district court learned that Boria had taken these medications and
asked several follow-up questions to confirm that Boria understood
the proceedings and felt “clearheaded.” Boria now argues that the
district court violated Federal Rule of Criminal Procedure 11 and his
constitutional rights because it did not sufficiently inquire into the
side effects and other impacts of his medications. We disagree.
Boria’s conduct during the plea hearing raised no red flags, so the
district court fulfilled its Rule 11 obligation to “explore on the record
defendant’s ability to understand the nature and consequences of his
decision to plead guilty” by confirming that Boria understood the
proceedings and felt clearheaded. United States v. Rossillo, 853 F.2d
1062, 1066 (2d Cir. 1988). In any event, Boria fails to show plain error
because there is no reasonable probability that he would not have
pleaded guilty but for the alleged error. We thus AFFIRM the
judgment of the district court.
Judge Lohier filed a separate opinion concurring in part and
concurring in the judgment.
S HAKIRA A. H ENDERSON, Rule 46.1(e) Law Student (Michael W.
Martin & Ian Weinstein, on the brief), Lincoln Square Legal Services,
Inc., Fordham University School of Law, New York, NY, for
Defendant-Appellant.

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J ACOB R. FIDDELMAN, Assistant United States Attorney, for
Matthew Podolsky, Acting United States Attorney for the Southern
District of New York, New York, NY, for Appellee.
PARK , Circuit Judge:
Steve Boria took medications for sleeping problems and bipolar
disorder the night before he pleaded guilty to conspiring to distribute
cocaine and possessing a firearm. During the plea colloquy, the
district court learned that Boria had taken these medications and
asked several follow-up questions to confirm that Boria understood
the proceedings and felt “clearheaded.” Boria now argues that the
district court violated Federal Rule of Criminal Procedure 11 and his
constitutional rights because it did not sufficiently inquire into the
side effects and other impacts of his medications. We disagree.
Boria’s conduct during the plea hearing raised no red flags, so the
district court fulfilled its Rule 11 obligation to “explore on the record
defendant’s ability to understand the nature and consequences of his
decision to plead guilty” by confirming that Boria understood the
proceedings and felt clearheaded. United States v. Rossillo, 853 F.2d
1062, 1066 (2d Cir. 1988). In any event, Boria fails to show plain error
because there is no reasonable probability that he would not have
pleaded guilty but for the alleged error. We thus affirm the
judgment of the district court.
I. BACKGROUND
In April 2017, Boria was indicted alongside eighteen co-
defendants for leading the “Slut Gang,” which sold narcotics, carried

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loaded guns, and committed acts of violence against rival gangs.
Boria himself distributed at least 28 grams of crack cocaine between
2010 and 2017 and discharged a gun around February 2014.
After most of Boria’s co-defendants pleaded guilty, Boria
decided to do so too. During his plea hearing before Magistrate
Judge Aaron, the following exchange took place:
THE COURT: Are you currently or have you recently been
under the care of a doctor or a mental health professional for
any reason? . . .
THE DEFENDANT: I’m not under the care of a doctor, but I do
take medication.
THE COURT: What medication do you take?
THE DEFENDANT: For sleeping problems and bipolar.
THE COURT: And for sleeping problems you take what type
of medicine?
THE DEFENDANT: Remeron. . . .
THE COURT: Remeron. And when was the last time you took
that medication?
THE DEFENDANT: Last night.
THE COURT: And what was the other medication that you
mentioned? For being – for bipolar?
[DEFENSE COUNSEL]: Your Honor, he doesn’t know the
name at the current time.
THE COURT: When was the last time you took that
medication?
THE DEFENDANT: Last night.
THE COURT: And are you under the influence of any alcohol
today?
THE DEFENDANT: No.
THE COURT: Since you took that medication last night – what
time did you take the medication?
THE DEFENDANT: 8 o’clock, 9.
THE COURT: As you’re sitting here now, are you clearheaded?

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THE DEFENDANT: Yes.
THE COURT: Do you understand what’s happening here in
court?
THE DEFENDANT: Yes, I do.
THE COURT: How are you feeling physically right now?
THE DEFENDANT: Good. . . .
THE COURT: And are you ready to enter a plea today?
THE DEFENDANT: Yes.
App’x at 48-50. Judge Aaron asked Boria’s counsel and the
government if they had “any objections to [Boria’s] competence to
plead at this time,” and both said no. Id. at 50. The court then
proceeded with the plea colloquy, during which Boria cogently
answered the district court’s questions. At the end of the
proceeding, the court found that Boria “underst[oo]d the nature of the
charges against” him and had made the plea “voluntarily and
knowingly.” Id. at 65. Judge Abrams accepted the plea and
sentenced Boria to a mandatory term of 15 years.
Boria requested that his counsel appeal the judgment and
sentence against him, but his counsel failed to file a timely notice of
appeal. The district court thus found that his counsel provided
ineffective assistance and held another hearing, at which it vacated
the judgment and sentence and re-entered it so that Boria could file
an appeal.1 Boria timely appealed the amended judgment.
1 At that hearing, Boria’s counsel said that “Boria has at times been
without his medication [in prison] and I will attest to the Court that . . . his
meds are incredibly helpful to him.” App’x at 101. Boria’s counsel thus
requested that the district court include in its amended judgment a
recommendation that the Bureau of Prisons ensure Boria consistently
receives all his medications, and the court did so.

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II. DISCUSSION
Boria argues that the district court violated Rule 11 of the
Federal Rules of Criminal Procedure and his constitutional rights
because it failed to inquire adequately into the types of medication he
took, their side effects, and their impact on him. We disagree.
We review for plain error because Boria did not raise this
objection to the district court. United States v. Adams, 768 F.3d 219,
223 (2d Cir. 2014). “Plain error review requires a defendant to
demonstrate that (1) there was error, (2) the error was plain, (3) the
error prejudicially affected his substantial rights, and (4) the error
seriously affected the fairness, integrity or public reputation of
judicial proceedings.” Id. (internal quotations omitted).
A. The District Court Did Not Err
Under Federal Rule of Criminal Procedure 11, before “the court
accepts a plea of guilty . . . the court must address the defendant
personally in open court” and “must inform the defendant of, and
determine that the defendant understands . . . [his] waiver of [his] trial
rights . . . [and] the nature of each charge” to which he is pleading
guilty. Fed. R. Crim. P. 11(b)(1)(F)-(G). Rule 11 “is designed to
assist the district judge in making the constitutionally required
determination that a defendant’s guilty plea is truly voluntary.”
Rossillo, 853 F.2d at 1065 (quotations omitted).
To ensure “strict compliance with Rule 11,” “if there is any
indication . . . that [a] defendant is under the influence of any
medication, drug or intoxicant, it is incumbent upon the district court
to explore on the record defendant’s ability to understand the nature
and consequences of his decision to plead guilty.” Id. at 1066. The
“critical question” in this inquiry “is whether the drugs—if they have
a capacity to impair the defendant’s ability to plead—have in fact
done so on this occasion.” United States v. Savinon-Acosta, 232 F.3d

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265, 268 (1st Cir. 2000). We review the “totality of the relevant
circumstances” to evaluate the “voluntariness of a guilty plea.”
Hanson v. Phillips, 442 F.3d 789, 798 (2d Cir. 2006).
We have twice vacated convictions based on a district court’s
failure to inquire adequately into the effects that medications had on
a defendant’s ability to plead guilty. First, in Rossillo, the district
court asked defendant if he was “under the influence of any drug,
alcohol or other intoxicants.” 853 F.2d at 1064. But it “never
received a definitive ‘yes’ or ‘no’ answer from defendant,” and
instead simply acknowledged that the defendant had a heart
condition. Id. at 1064-65. We vacated the plea because the district
court failed to “determine[] the voluntariness of the guilty plea based
upon on-the-record responses to its questions,” and instead
“assumed that defendant’s condition did not interfere with his mental
capabilities.” Id. at 1065.
Second, in United States v. Yang Chia Tien, the defendant told
the district court that he took “medication for blood pressure,
diabetes, and pain,” and that “he understood only fifty percent of
what was happening.” 720 F.3d 464, 466, 469 (2d Cir. 2013). He
responded, “yeah” when asked “whether his medications affected his
ability to ‘hear or think,’” and said “no” when “asked again whether
[he] understands the court.” Id. at 469-70 (cleaned up). We
concluded that this exchange “should have caused the district court
to conduct further investigation into whether [defendant] understood
the proceedings.” Id. at 469. And we vacated the plea because
there was “no indication that after the district court learned that
[defendant] took medications, it endeavored to ascertain whether
they could impact his ability to proceed.” Id. at 470. We also
vacated a subsequent plea involving the same defendant because the

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district court “failed to ask any questions about the medicine
[defendant] was taking.” Id. at 471.
Here, in contrast, the district court did “endeavor[] to ascertain”
whether Boria’s medications “could impact his ability to proceed,” id.
at 470, and it did “determine[] the voluntariness of the guilty plea
based upon on-the-record responses to its questions,” Rossillo, 853
F.2d at 1065. It asked Boria, “As you’re sitting here now, are you
clearheaded?” and “Do you understand what’s happening here in
court?” and Boria answered both questions affirmatively. App’x at
49-50. The court also asked the government and Boria’s counsel if
they had objections to Boria’s competency, and both said no. We see
no red flags in the record that suggest Boria did not “understand the
nature and consequences of his decision to plead guilty” during the
plea hearing. Rossillo, 853 F.2d at 1066. Considering the “totality of
the relevant circumstances,” Hanson, 442 F.3d at 798, the district
court’s inquiry satisfied its Rule 11 obligation.2
2 Several of our sister circuits have reached the same conclusion
based on similar records. See, e.g., Savinon-Acosta, 232 F.3d at 269 (district
court made “no error in accepting the plea” when defendant said his
medication did not affect his ability to understand the district court, and
defendant’s answers during the plea “bore out the defendant’s claim of
clearheadedness”); United States v. Nicholson, 676 F.3d 376, 383 (4th Cir.
2012) (affirming when district court “asked whether [defendant] was sober
and understood what he was doing,” defendant “responded in the
affirmative,” and “the government and defense counsel [had] an
opportunity to raise issues about the competency of the defendant’s guilty
plea, but neither did”); United States v. Hardimon, 700 F.3d 940, 942 (7th Cir.
2012) (affirming when district court “asked [defendant] whether he could
think clearly, and he had said he could, which implies that he didn’t think
his medications were affecting his ability to think clearly,” and defendant
had been “alert and responsive and exhibited no signs of confusion” at the
plea hearing); United States v. Dalman, 994 F.2d 537, 538-39 (8th Cir. 1993)
(affirming when, after defendant said he “was taking four different types

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Boria argues that the district court should have asked him
about the “side effects” of his medications, pointing to our
observation in Yang Chia Tien that the district court there made no
“on-the-record finding as to the side effects of [defendant’s]
medications and whether they interfered with his understanding of
the proceedings.” 720 F.3d at 470. We agree that a district court
must ask questions about the side effects of a medication that are
relevant to a defendant’s ability “to understand the nature and
consequences of his decision to plead guilty.” Rossillo, 853 F.2d at
1066; see also Yang Chia Tien, 720 F.3d at 471 (“[W]hen a court learns
that a defendant is on medications, it must determine on the record
that they are not interfering with the defendant’s understanding of
the plea.”). For instance, a district court may ask whether the
medication has affected the clarity of a defendant’s thinking or a
defendant’s ability to understand the proceeding. But the district
court made that inquiry when it asked Boria whether he felt
“clearheaded” and understood “what’s happening here in court.”
of pills, the prescription names of which he could not recall,” the court
asked defendant “whether he understood what was happening ‘right
now,’” and defendant said yes, and there was “nothing in the record to
indicate that [defendant] was not fully in possession of his faculties during
the proceedings”). And we have reached similar conclusions in summary
orders. See, e.g., United States v. Re, 682 F. App’x 33, 35-36 (2d Cir. 2017)
(affirming on plain error review when district court “questioned
[defendant] about both his psychiatric treatment and his medication, as
well as the effect of those medications on defendant’s mental state,”
defendant’s responses “were not such as to undermine the court’s finding
that he was competent,” and defendant’s attorneys said they believed
defendant was competent); United States v. Brooks, 756 F. App’x 52, 56 n.1
(2d Cir. 2018) (affirming when district court “asked [defendant] whether
the medications impacted her ability to understand the
proceedings . . . [and defendant] confirmed that they did not,” and
defendant said “that she was entering the plea voluntarily and that she
understood her rights”).

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App’x at 49-50. Boria’s answers indicated that his medications were
“not interfering with [his] understanding of the plea.” Yang Chia
Tien, 720 F.3d at 471. So the district court’s inquiry correctly focused
on Boria’s ability during the plea “to understand the nature and
consequences of his decision to plead guilty,” Rossillo, 853 F.2d at
1066, and it did not need to inquire further about the side effects of
Boria’s medications.
B. There Was No Effect on Boria’s Substantial Rights
A “defendant who seeks reversal of his conviction after a guilty
plea, on the ground that the district court committed plain error
under Rule 11, must show a reasonable probability that, but for the
error, he would not have entered the plea.” United States v.
Dominguez Benitez, 542 U.S. 74, 83 (2004). Boria has not shown that
reasonable probability.
Instead, Boria argues that he does not need to establish
prejudice because this error was “structural.” That is incorrect.
“[S]tructural errors are a very limited class of errors that affect the
framework within which the trial proceeds,” United States v. Marcus,
560 U.S. 258, 263 (2010) (internal quotations omitted), and the
“omission of a single Rule 11 warning without more is not colorably
structural,” Dominguez Benitez, 542 U.S. at 81 n.6. We thus require a
showing of prejudice to establish “plain error” under Rule 11, even
when the error relates to the court’s duty to ensure a defendant has
made a voluntary plea. See Adams, 768 F.3d at 223 (finding no plain
error because defendant “has not demonstrated any reasonable
probability that he would not have pleaded guilty”); cf. Yang Chia
Tien, 720 F.3d at 471 (finding plain error because “there is a reasonable
probability that [defendant] would not have entered the plea if
[defendant’s] medications and comprehension had been properly
examined”).

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III. CONCLUSION
The district court did not err and Boria established no
prejudicial effect on his substantial rights. We affirm the judgment
of the district court.

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LOHIER, Circuit Judge, concurring:
I concur in Part II.B of the majority opinion, which fully resolves this
appeal based on Boria’s failure to demonstrate prejudice on plain error review.
As Part II.B explains, Boria has not shown a reasonable probability that he would
not have entered his plea but for the District Court’s purported Rule 11 error. In
my view, nothing more needs to be said.

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