United States v. Boria cocaine conspiracy firearm possession appeal

24-1871 United S tates v. B oria United States Court of Appe als for the Se cond Circui t August Ter m 2025 Argued: October 24, 2025 Decided: February 4, 2026 No. 24-1871 U NITED S TATES OF A MERICA, Appellee, v. S TEV E B ORIA, AKA C HROME, Defendant-Appellant. * Appeal from the Uni ted States Dis trict C our t for the Southern District of New Yor k No. 17- cr -00142 Ronnie Abrams, Ju dge. Before: K EARSE, L OHIER, and P ARK, Circuit Judges. * The Cl erk of the C ourt i s resp ectfu lly direc ted to am end the capti on as se t forth ab ove.

2 Steve Boria took med ications for sleeping pr oblems and bipolar disorder the night be fore he pleaded guilty to cons piring to distribute cocaine and possess ing a firearm. Dur ing th e p lea c ollo qu y, t he district court learned th at Boria had taken these medications and asked several fo llow - up que stions to con firm that Boria understood the proceedi ngs and felt “clea rheaded.” Boria now argues th at the distri ct court violated Federa l Rule of Criminal Proced ure 11 and his cons titut iona l r ights be cause it did n ot s uffic ien tly in quir e in to the side effects and o ther imp acts of his medications. We disagree. Boria’s conduct dur ing the plea hear ing raised no re d flags, so t he distr ict c our t f ulfil le d its Ru le 1 1 ob liga ti on to “ explore on the record defendant’s ab ility to unders tand the nature and conse quences of his decis ion t o plea d g uilt y ” by confirming that Boria understood the proceedings and fe lt clearheaded. Unite d States v. Ross illo, 853 F.2 d 1062, 106 6 (2d Cir. 1988). In any event, Boria fa ils to show plain error because the re is no reasonable probabi lity that he would no t have pleaded guilty but for the alleged error. We thus AFFI RM the judgmen t of the distr ict co urt. Judge Lohier filed a separate opin ion concurr ing in part and concurring in the judgment. S HAKIRA A. H ENDER SON, Rule 46.1(e) Law Student (Mich ael W. Martin & Ian We inst ein, on the brief), Linc oln Sq uare Legal Serv ices, Inc., Fordham Un iversity Schoo l of Law, Ne w York, NY, for Defendant-Appellant.

3 J ACOB R. F IDDELMA N, As sistant Un ited States Atto rney, for Matthew Podo lsky, Actin g Un ited S tates Attor ney for the So uther n District of New Y ork, New Yor k, NY, for Appellee. P ARK, Circuit Judge: Steve Boria took med ications for sleeping pr oblems and bipolar disorder the night be fore he pleaded guilty to cons piring to distribute cocaine and possess ing a firearm. Dur in g the p le a co lloqu y, t he district court learned that Boria had taken thes e medications and asked several fo llow - up que stions to con firm that Boria understood the proceedings an d felt “clearheaded. ” Boria now argues th at the distri ct court violated Federa l Rule of Criminal Proced ure 11 and his cons titut iona l r ights be cause it did n ot s uffic ien tly in quir e in to the side effects and o ther imp acts of his medications. We disagree. Boria’s conduct dur ing the plea hear ing raised no re d flags, so t he distr ict c our t f ulfil le d its Ru le 11 ob ligat ion to “ explore on the record defendant’s ab ility to unders tand the nature and conse quences of his decis ion t o plea d g uilt y ” by confir ming that Boria understoo d the proceedings and fe lt clearheaded. Unite d States v. Ross illo, 853 F.2 d 1062, 1066 (2d Cir. 1 988). In any event, Boria fa ils to show plain error because there is no reasonable prob ability that he would not have pleaded g uilty but for t he alle ged error. We thus affirm the judgmen t of the distr ict co urt. I. BACKGROUND In April 2017, Bori a was indicted alon gside eighteen co - defendants for leadi ng the “Slut Gang,” which sold narcotics, carried

4 loaded guns, an d c ommitted acts of violence ag ainst rival gangs. Boria himself distributed a t least 28 grams of crack coca ine between 2010 and 2017 and discharged a gun around Fe bruary 2014. After most of Boria’s co -defendants plea ded g uilt y, Boria decided to do so too. D urin g his plea hearing before Magistra te Judge Aaron, t he following exch ange took place: THE COURT: A re you currently or h ave you recentl y been under the care of a doctor or a mental health profes sional for any reason? . . . THE DEFENDAN T: I’m not under the car e of a doct or, but I do take me dic atio n. THE COURT: Wh at medication do yo u take? THE DEFENDAN T: For sleeping problems and b ipolar. THE COU RT: And for sleeping p roblem s you take what typ e of medicine? THE DEFENDAN T: Remeron. . . . THE COURT: Remeron. A nd when was the last time y ou took that medication? THE DEFENDAN T: Last night. THE COU RT: A nd wh at was th e oth er medicati on tha t yo u mentioned? For being – for bipolar? [DEFENSE COUNS EL ]: Your H onor, he doesn ’ t k now th e name at the current time. THE COURT: When was the last time you took that medication? THE DEFENDAN T: Last night. THE COURT: And a re you under the influence of any alcohol today? THE DEFENDAN T: No. THE COURT: Since you t ook that medication last ni ght – wha t time did you take the medication? THE DEFENDAN T: 8 o’clock, 9. THE COURT: As you ’re sitting here n ow, are you clearheaded?

5 THE DEFENDAN T: Yes. THE COURT: Do you understand what’s happening here i n court? THE DEFENDAN T: Yes, I do. THE COUR T: How a re you fee ling phys ically r ight now? THE DEFENDAN T: Good. . . . THE COURT: And are you re ady to enter a plea today? THE DEFENDAN T: Yes. App’x at 4 8-50. Judge Aaron as ked Bor ia’s counsel and th e governmen t if t he y had “ any objec tions to [Bor ia’s] compete nce to plead at this time,” and both said no. Id. at 50. The cour t then proceeded with th e p lea c olloq uy, d uring whic h B or ia c og ently answered th e district court’s questio ns. A t the e nd of the proceeding, the court found th at Boria “unde rst [oo] d the na ture of the charges against” hi m and had made the plea “voluntari ly and knowingly. ” Id. at 65. Judge Ab rams accepted the plea and sentenced Boria to a mandatory ter m of 15 year s. Boria reques ted that hi s counsel appeal the judgm ent and sentence against him, but his counsel f ailed to f ile a ti mely no tice of appeal. The dis trict co urt thus found that his counsel provided ineffective assistance and held another hearing, at which it vacated the judgment and sentence and re - enter ed it so that B or ia could fi le a n appeal. 1 Boria timely appe aled the amended judgment. 1 At that he aring, B oria ’s c ouns el said that “Boria h as at ti mes b een without his medication [in prison] and I will atte st to the Cou rt tha t. . . his meds are incredibly helpful to him.” App ’ x at 101. Boria’s counsel thus requested that the district co urt include in its amended judgment a recomm endati on that the B ureau of Pris ons ensure Boria c onsis tently receives all his medicat ions, and the court did so.

6 II. DISCUSSIO N Boria argues th at th e district court violated R ule 11 of the Federal R ules of Crim inal Pro cedure and his cons titu tion al r ights because it failed to inq uire adequately int o the types of medication he took, their side effec ts, and their impact on h im. We disagree. We review for plain erro r because Boria did not ra ise this objection to th e dis trict co urt. United Sta tes v. Adams, 768 F.3 d 219, 223 (2d Cir. 2 014). “ Plain error review require s a defendant to demonstrate that (1) there was error, (2) the error was plain, (3) the error prejudic ially affected his s ubstantial ri ghts, and (4) the er ror seriously affected the fairness, integr ity or public reputat ion of judi cia l pr ocee din gs. ” Id. (internal q uota tions o mitted). A. The Distr ict Co urt D id Not E rr Under Federal Rul e of Criminal P rocedure 11, bef ore “the cou rt accepts a p lea of g uilty. . . the court must address the defe ndant personally in ope n c ourt” and “ must inf orm the defe ndant o f, and determine that the defendant un derstands. . . [his] wa iver of [hi s] trial rights. . . [and] the nature of each charg e” to which he is pleading guilty. Fed. R. Crim. P. 11(b)(1)(F) - (G). Rul e 11 “is des igned to assis t the d ist ric t jud ge in mak ing th e con stit utio nal ly r equir ed determination th at a defendant ’s guilty plea is truly volu ntary.” Rossillo, 853 F.2d at 1 065 (quotations om itted). To ensure “s trict compliance with Rule 11,” “if there is any indication.. . that [a] defendant is under the influence of any medication, drug or in toxicant, it is incumbe nt upon the district court to explore on the rec ord defendant ’s abili ty to unde rstand the nature and consequences of h is decision to plead guilty.” Id. at 1066. The “critica l question” i n this inquiry “is whether the d rugs — if they have a capacity to impair the defe ndant’s abi lity to plead — h ave in fact done so on this occasion.” United States v. Savinon -A costa, 232 F.3d

7 265, 268 (1st Cir. 2000). We review th e “to tal ity of the re levan t circumstances” to evaluate the “volunt ariness of a g uilty p lea.” Hanson v. Phillips, 44 2 F.3d 789, 798 (2d Cir. 2006). We have twice vacate d convictions bas ed on a d istri ct cou rt ’s failure to inqu ire adeq uately into the effects th at medications had on a defendant’ s ab ility to plead gu ilty. First, i n Rossillo, the dis tric t court asked defend ant if he was “ under the influence of any drug, alcohol or other intoxicants.” 853 F.2d at 1064. Bu t it “never received a defin itive ‘yes ’ or ‘no’ ans wer from defendant,” and instead simply ack nowledged that the de fendant had a hear t condition. Id. at 10 64 -65. We vacated the p lea because the dist rict court failed to “ determine[] the voluntar iness of the guilty plea b ased upon on - the - recor d respon ses to its questions,” and instead “ assumed that de fendant ’ s cond it ion d id n ot in t erfere with his mental capab ilit ies. ” Id. at 1065. Second, i n Uni ted St ates v. Yang Chia Tie n, the defendant to l d the distr ict cour t th at he took “ medication for b lood pres sure, diabetes, and pain,” and that “he under stood only fi fty perc ent of what was happening.” 720 F.3d 464, 466, 469 (2d C ir. 2013). H e responded, “ yeah” whe n asked “whethe r his medicati ons affected h is ability to ‘hear or th ink,’” and sa id “ no ” when “asked again whether [he] understands the court.” Id. at 46 9- 70 (cleaned up). We concluded that this exchange “should have caused the distric t court to conduct further inve stigation into whethe r [defendant] unde rstood the proceedings. ” Id. at 469. And we vacated the p lea because there was “ no indication that af ter the distr ict cour t lear ne d that [defendant] took medications, it endeavore d to ascertain whether they could impact his ab ility to procee d.” Id. at 470. We a lso vacated a subsequen t plea involving the same defendant because the

8 district court “fa iled to ask any q uestions abo ut the medicine [defendant] was tak ing.” Id. at 471. Here, in contr ast, the distric t co urt did “endeavor[] to as certain ” whether Boria’s med ications “could impac t his abilit y to procee d,” id. at 470, and it did “determine[] the volu ntariness of the guilty plea based upon on - th e - r ecord response s to its q uestions,” Ros sillo, 853 F.2d at 1065. It as ked Boria, “ As you’re sitting he re now, are you clearheaded? ” and “ Do you underst and what’s happeni ng her e in court? ” and Boria answe red both quest ions affir matively. A pp’x at 49- 50. The c ourt also asked the government and Bor ia’s couns el if they had ob jections t o Boria’s competenc y, and b oth said no. We see no red flags in the recor d that suggest Bor ia did not “ understand the nature and conse quences of his dec ision to plea d guilty” duri ng the plea hearing. Rossill o, 853 F.2d at 1066. C onsidering the “ totality of the releva nt circumstances,” Hanson, 442 F.3d at 798, t he dis tric t court ’s in qu iry s atis fi ed its Ru le 1 1 obl iga tion. 2 2 Sev eral of our si ster cir cuits ha ve r eached th e same co nclusi on based o n simil ar r ecor ds. S ee, e.g., S avinon - Acosta, 232 F.3d at 26 9 (distr ict court made “no err or in accepting the ple a” when de fendant s aid his medication did not affect his ability to understand the distr ict court, and defendant’s answers during the plea “bore out t he defendant’s claim o f clearheadedness ”); United States v. Nichols on, 676 F.3d 376, 383 (4th Cir. 2012) (affirming when distr ict court “ a sked whet her [defendant ] was so ber and understo od what he was do ing, ” de fendant “ respo nded in t he affirmat ive,” and “the go vernment a nd defense cou nsel [h ad] an opportun ity t o raise is sues abou t the com petenc y of the defendant ’s guilty plea, but neither did”); United States v. Hardimon, 700 F.3d 940, 942 (7 t h C ir. 2012) (affirmi ng when distr ict cour t “ ask ed [defe ndant] whe ther he could think clearly, a nd he had said he co uld, whic h implies that he did n’ t think his medications were affecting his ability t o think clearly,” and d efendant had been “alert and responsive and exhibite d no signs of confusion” at the plea hearing); United Stat es v. Dalman, 994 F.2d 537, 53 8-39 (8th Cir. 1993) (affirming when, a fter defendant sa id he “was taking f our dif feren t types

9 Boria a rgues tha t the distri ct cour t sho uld have asked him about the “ side effects ” of his med ications, po inting to our observation in Yang Chia Tien th at the di strict co urt there ma de n o “on- the - record find ing as to the side effects of [defendant’s] medication s and whether the y interfe red with his und erstanding o f the proceedings.” 720 F.3d at 470. We agree that a district court must ask questions about th e sid e effects of a medication th at are relevant to a de fendant’s ab ility “to understand the nature and conseque nce s of h is dec ision to plea d gu ilt y.” Rossillo, 853 F. 2 d at 1066; see also Y ang Chia Tien, 720 F.3d at 471 (“[W]hen a cour t learns that a defendan t is on medications, it mus t determine on the record that they are not interfering with the defendant ’ s understanding of the plea.”). For instance, a district co urt may ask whether the medication h as affe cted the clarity of a defendant’s th ink in g o r a defendant’s ability t o understand the proceeding. But the distr ict court made that inquiry when it asked Boria wheth er 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 understoo d w hat was happening ‘r ight now,’” and defendant said yes, a nd ther e was “ nothing in the record to indicate that [defe ndant ] was not fully in possession of his fa culties during the proceeding s ”). And w e have reached similar conclusion s in summa ry orders. See, e.g., United States v. Re, 682 F. App’x 33, 35 - 36 (2d Ci r. 2017) (affirming on plain er ror review when district court “ questioned [defendant ] about b oth h is ps ychi atric treatment and his medication, as well as the eff ect of those medications on defen dant ’ s men tal state, ” defendant ’ s r espo nses “ were not suc h as to underm ine th e court ’ s f inding that he w as c ompete nt,” and defendant’s attorney s said they believed defendant was competent); Un ited States v. Brooks, 756 F. App’x 52, 56 n.1 (2d Cir. 2018) (a ffir ming whe n dist rict co urt “ asked [de fenda nt] whe ther the medications impacted her a bility to understand the proceedings. . . [and defendant] co nfirmed that the y did not,” and defendant said “ that she was e ntering th e p lea volu ntarily and tha t she unde rstood her rights ”).

10 App’x at 49 -50. Boria’s ans wers ind icat ed that his med icat ion s were “ not interferi ng with [his] understanding of the plea.” Yang Chia Tien, 720 F.3d at 471. So the distr ict court’s inquiry c orre ctly focused on Boria ’s a bility during the plea “ t o unders tand the nat ure and consequences of his decision t o plead guil ty,” Rossillo, 853 F. 2 d at 1066, and it did no t need to inquire furt her about the side effects of Boria’s medications. B. There Was No Effec t on Boria’s Subs tan tia l Rig hts A “defendant who se eks reversal of his co nviction after a gui lty plea, on the ground that the distri ct court committe d plain error under Rule 11, must show a reasonab le prob ability that, bu t 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 probabi lity. Instead, Boria argues that he does no t need to e stablish prejudi ce because thi s error was “st ructural.” That is incorrect. “[S] tructura l errors are a very limit ed class of errors tha t affect the framework within which the trial proceeds,” United States v. Marcus, 560 U.S. 258, 263 (2010) (internal quotations omitted), an d the “ omiss ion of a sin gle R ule 11 warning wit hout more is not col orably structura l,” Doming uez Benitez, 542 U.S. at 81 n.6. We thus require a showing of prej udice to es tab lish “plain error” under Rul e 11, even when the error rel ates to th e court’s duty to ensu re a defen dant has made a voluntary plea. See Adams, 768 F.3d at 223 (f ind ing no pla in error because defendant “ has not de monstrated any r easonab le probability that he would n ot have pleaded guilty ”); cf. Yang Chia Tien, 720 F.3d a t 471 (finding p lain error because “there is a reasonable probab ility th at [defendant] would not have entered the plea if [defendant’s] medications and compreh ension had been properly examine d ”).

11 III. CONCLUSIO N The distr ict co urt d id not e rr and Boria estab lished no prej udic ial e ffec t on his sub stan tia l r ights. We aff irm t he judgme nt of the district court.

LOHIER, Circuit Jud ge, concurring: I concur in P art II. B of the majori ty opinion, which ful ly resolves this appeal based on Bor ia’s failure to de monstrate pre judice on plain error review. As P art II. B explains, Boria has no t shown a re asonable probab ility that he would not hav e ent ered his plea but for the Dis tric t Cour t’ s purported Rule 11 error. In my view, nothin g more needs to be said.