In United States v. Boria, the Second Circuit (Kearse, Lohier, and Park) addressed whether a district court violated Federal Rule of Criminal Procedure 11 and a defendant’s constitutional rights because it did not sufficiently inquire into the side effects and other impacts of the medications that the defendant took the night before his plea colloquy. The Court held that the questions the district court asked about defendant’s medication fulfilled its Rule 11 obligation because the district court confirmed that Boria understood the proceedings and felt clearheaded. The Court also held that Boria failed to show plain error because there was no reasonable probability that he would not have pleaded guilty but for the alleged error. Judge Lohier wrote separately, concurring in part and concurring in the judgment. The decision is notable as a reminder that guilty pleas should not proceed if the defendant is unwell, and that counsel should work with his or her client to confirm this prior to the beginning of the plea, to raise an objection to the plea if the defendant feels unable to proceed.

Background

In April 2017, Boria was indicted alongside co-defendants for conspiracy to distribute cocaine and possess a firearm in relation to his leadership in a gang that sold narcotics, carried loaded guns, and committed acts of violence against rival gangs. Like most of his co-defendants, Boria decided to plead guilty. During his plea hearing in front of Magistrate Judge Aaron, Boria was asked whether he was under the care of a doctor or medical health professional. In response, Boria mentioned that he takes medication. After follow-up questions from the Court, Boria stated that the medications were for sleeping problems and bipolar disorder, that his sleeping medication was called Remeron, but he could not remember what medication he took for his bipolar disorder, and that he last took both medications the prior night at around 8 or 9 o’clock.

The Magistrate Judge then asked Boria, “As you’re sitting here now, are you clearheaded?” Boria responded “yes.” The Judge then asked, “Do you understand what’s happening here in the court?” to which Boria responded “yes, I do.” Finally, the Judge asked, “How are you feeling physically right now?”, Boria answered “Good,” the Judge asked, “Are you ready to enter a plea today?” and Boria responded “Yes.” Upon further inquiry from Magistrate Judge Aaron, neither Boria’s counsel nor the government had any objections to Boria’s competence to plead guilty. The Judge then proceeded with the plea colloquy, during which he found that Boria understood the nature of the charges against him and had made the guilty plea voluntarily and knowingly. The district court later accepted the guilty plea and sentenced Boria to a mandatory term of 15 years imprisonment.

The Opinion

On appeal, the Second Circuit evaluated Boria’s claim that the district court violated Federal Rule of Criminal Procedure 11 and his constitutional rights by failing to adequately inquire into the types of medication he took, their side effects, and their impact on him. The Court conducted plain error review, as Boria did not raise these objections to the district court at the time of his guilty plea or when the district court accepted the guilty plea.

“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.” United States v. Adams, 768 F.3d 219, 223 (2d Cir. 2014). Federal Rule of Criminal Procedure 11 requires that, before the court accepts a guilty plea, “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).

The Court first determined that the district court did not violate Rule 11. Pursuant to prior Second Circuit caselaw, 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.” United States v. Rossillo, 853 F.2d 1062, 10 (2d Cir. 1988). In this case, the Court adopted an additional standard from the First Circuit, stating that the “critical question” in the 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 265, 268 (1st Cir. 2000).

The Court held that, in contrast to prior cases where they vacated a conviction, the trial court here did try to ascertain whether Boria’s medications could impact his ability to proceed and therefore did determine that the guilty plea was actually voluntary. The Court specifically pointed to the Magistrate Judge’s questions “As you’re sitting here now, are you clearheaded?” and “Do you understand what’s happening here in court?” and Boria’s answers to both in the affirmative, as well as a lack of any other indication in the record suggesting that Boria did not understand the nature of his decision to plead guilty, as evidence that the district court’s inquiry satisfied its Rule 11 obligation.

The Court rejected Boria’s argument that the Magistrate Judge should have asked him about the side effects of his medication. In this case, the district court did inquire as to whether the medication affected the clarity of Boria’s thinking and ability to understand the proceedings. It therefore did not need to inquire further about the side effects of Boria’s medications.

The Court also held that Boria did not establish prejudice, that is, show a reasonable probability that, but for the district court’s error, he would not have entered the plea. It rejected Boria’s argument that he was relieved of the requirement to demonstrate prejudice because the error was “structural,” noting that the “omission of a single Rule 11 warning without more is not colorably structural,” United States v. Dominguez Benitez, 542 U.S. 74, 83 (2004), and therefore Boria was not excused from demonstrating prejudice.

Judge Lohier wrote separately, concurring with the part of the majority’s opinion finding that Boria failed to demonstrate prejudice on plain error review. Like the majority, Judge Lohier found that Boria had not shown a reasonable probability that he would not have entered his plea but for the District Court’s purported Rule 11 error, but did not think the Court needed to address any other aspect of Boria’s appeal.

Commentary

In this opinion the Second Circuit provided additional guidance to district courts regarding the types of questions that can help determine whether a defendant who is taking medication is able to understand the nature and consequences of his decision to plead guilty, such that a guilty plea is constitutional. The Court did not mandate that a district court must, for example, ask a defendant about the side effects of the medication in every instance, but rather endorsed a more general approach that inquired into the defendant’s mental state as he appeared before the court. Questions like “are you clearheaded?” and “do you understand what’s happening here in court?” gave the district court the ability to determine that the defendant understood the nature of the charges against him and made the plea voluntary and knowing to the Second Circuit’s satisfaction. These questions belong in every district judge’s colloquy checklist, to make sure that the defendant’s rights are honored. In addition, the Second Circuit also pointed to the fact that neither defendant’s counsel nor the government, when asked specifically by the judge overseeing the plea colloquy, had objections to the defendant’s competence, indicating that similar questions to counsel can also help a judge determine a defendant’s ability to plead guilty.

This opinion also demonstrates the potential danger in arguing only that an error is structural and therefore, on plain error review, a defendant need not demonstrate prejudice, as opposed also to making the argument in the alternative that a defendant was prejudiced by the error. Although here the Second Circuit found that the district court did not err in the first place, if it had decided the error prong in the defendant’s favor, the fact that the defendant did not try to argue that he was prejudiced by the error would have meant he had no opportunity to prevail if the court (as it did here) found that the error was not structural.

Finally, Judge Lohier’s concurrence on plain error suggests that there may be some judges on the Second Circuit who might have decided the issue differently, if there had been an objection. Of course, if defense counsel objected to proceeding with the change of plea proceeding, it is possible that the district court would have adjourned the plea and there would have been no appeal. It is also possible, in a given case, that the government’s plea offer might expire if defense counsel seeks an adjournment of the guilty plea. This could be to a client’s disadvantage. There are no easy answers when a client is medicated. In any event, defense counsel should inquire with their clients prior to pleading guilty if the client is on medication and to make sure that any objection is preserved, if the defendant is unable to make an informed and competent decision to plead guilty.