Court Opinion

ID: 6325217
Source: CourtListenerOpinion
Date Created: 2022-03-21 18:00:30.84465+00
Date Added: 2024-06-11T09:19:45.600478
License: Public Domain

Appellate Case: 20-5089     Document: 010110660067      Date Filed: 03/21/2022    Page: 1
                                                                                  FILED
                                                                      United States Court of Appeals
                                       PUBLISH                                Tenth Circuit

                        UNITED STATES COURT OF APPEALS                      March 21, 2022
                                                                         Christopher M. Wolpert
                              FOR THE TENTH CIRCUIT                          Clerk of Court
                          _________________________________

  UNITED STATES OF AMERICA,

        Plaintiff - Appellee,

  v.                                                          No. 20-5089

  JOHN MICHAEL McINTOSH,

        Defendant - Appellant.
                       _________________________________

                      Appeal from the United States District Court
                        for the Northern District of Oklahoma
                           (D.C. No. 4:19-CR-00059-JED-1)
                        _________________________________

 John M. Bowlin, Bowlin & Schall LLC, Greenwood Village, Colorado, for Defendant-
 Appellant.

 Eleanor F. Hurney, Assistant United States Attorney (Clinton J. Johnson, Acting United
 States Attorney, with her on the briefs), Tulsa, Oklahoma, for Plaintiff-Appellee.
                         _________________________________

 Before McHUGH, EBEL, and EID, Circuit Judges.
                   _________________________________

 EBEL, Circuit Judge.
                          _________________________________

       Defendant-Appellant John Michael McIntosh pled guilty to five counts of

 robbery in violation of 18 U.S.C. § 1951, plus three counts of brandishing a pistol

 during those five robberies in violation of 18 U.S.C. § 924(c). During the change-in-

 plea hearing held by the district court, however, Mr. McIntosh repeatedly expressed
Appellate Case: 20-5089    Document: 010110660067         Date Filed: 03/21/2022     Page: 2

 doubts about whether he should plead guilty and suggested that his mental capacity

 was impaired. After much indecision and two off-the-record discussions with the

 government, he finally went forward with the plea and the district court completed its

 plea colloquy.

       But two months after entering the plea, Mr. McIntosh filed a motion to

 withdraw it, contending that the plea was neither knowing nor voluntary and

 therefore violated his constitutional due process rights. The district court denied the

 motion and accepted the plea agreement at sentencing. Mr. McIntosh now appeals,

 arguing that the plea was constitutionally invalid in the first instance and also

 arguing, in the alternative, that the denial of his motion to withdraw the plea was an

 abuse of discretion. Exercising jurisdiction under 28 U.S.C. § 1291, we find that the

 district court failed to ensure the plea was knowingly and voluntarily made, and so

 we VACATE Mr. McIntosh’s convictions and REMAND for further proceedings.

                                    I.     BACKGROUND

       A grand jury charged Mr. McIntosh with five counts of Hobbs Act robbery, in

 violation of 18 U.S.C. § 1951, and five counts of brandishing a firearm during the

 robberies, in violation of 18 U.S.C. § 924(c), based on allegations that he robbed five

 Oklahoma convenience stores and other retail establishments at gunpoint over a

 period of six days in February 2019.

       Before trial, at the request of defense counsel and by order of the district court,

 a psychologist examined Mr. McIntosh and diagnosed him with substance abuse

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 disorders and malingering. The evaluator concluded that Mr. McIntosh did not meet

 the diagnostic criteria for any mood, depressive, or psychiatric disorder that would

 render him unable to understand the proceedings against him. The district court

 subsequently found Mr. McIntosh competent to stand trial.

        About a month before trial was scheduled to begin, Mr. McIntosh notified the

 district court that he intended to plead guilty pursuant to an agreement with the

 government. The agreement stipulated that Mr. McIntosh would plead guilty to eight

 of the ten charges and be sentenced to 300 months’ imprisonment, while the

 government would dismiss two of the brandishing counts against him. In advance of

 a change-in-plea hearing, Mr. McIntosh signed the plea agreement documents,

 including a statement attesting that he had reviewed the entire agreement with

 counsel, understood all provisions, and voluntarily agreed to the deal.

        But at the beginning of the district court’s change-in-plea hearing on

 November 1, 2019, Mr. McIntosh voiced doubts about the agreement, stating:

                        I just feel like—honestly I feel like that it’s too much
                time in my opinion. And I haven’t been taking my
                medication because they took me off of it in David L. Moss
                [Criminal Justice Center]. And I just don’t feel like my
                judgment is right, you know what I’m saying? I just feel
                like—I’m all over the place. You know, I want to take the
                deal, I don’t want to take the deal. And I feel like my mental
                state of mind isn’t right to take anything right now because
                I don’t understand, you know, what’s really going on.

 (R., vol. II at 16.)

        The district court responded that Mr. McIntosh seemed to “need[] some other

 time,” and asked Mr. McIntosh’s counsel for their thoughts. (Id. at 17.) Counsel

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 replied that Mr. McIntosh had a “basic understanding” of the plea agreement and

 appeared to be competent, and noted that the government’s plea offer was likely the

 best option for him. (Id. at 18.) At that point, the government offered to speak with

 Mr. McIntosh and his counsel off the record to explain the plea agreement in more

 detail. The court agreed and granted recess, during which the parties conferred.

       Upon returning from recess, Mr. McIntosh told the court that he would “just

 take the deal.” (Id. at 22.) The court proceeded to explain some of the terms of the

 plea agreement to him and stated, “I think what the government and the defense

 counsel have done is something that would be better for you.” (Id. at 22.) The court

 then administered an extensive plea colloquy, asking Mr. McIntosh and his counsel

 questions such as whether he suffered from any mental disability or whether there

 was any reason the hearing should not proceed. No objections or reasons not to

 proceed were given.

       After the court discussed the rights being waived and the precise terms of the

 plea agreement with Mr. McIntosh, Mr. McIntosh asked to speak with his lawyer. He

 was allowed to do so, and when the hearing resumed his counsel informed the court

 that Mr. McIntosh had changed his mind again and now wished to go to trial. The

 court said, “All right. You understand the difference? . . . You know that whatever

 the government has told you about, you know, for 25 years here, the government can

 go a lot further?” (Id. at 39–40.) Mr. McIntosh said he did understand and confirmed

 that trial was what he wanted.

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       The government requested to speak with Mr. McIntosh again. The court

 allowed them to have an off-the-record conference. After this second conference

 with the government, Mr. McIntosh again indicated he was willing to proceed with

 the plea agreement. The court said, “All right. Thank you. If it helps, I think it’s the

 right thing you did, all right?” (Id. at 40.) Mr. McIntosh then confirmed that he was

 satisfied with his representation and told the court there was no reason why it should

 not accept his guilty plea. The hearing proceeded with the government stating the

 facts underlying the charges, Mr. McIntosh expressly pleading guilty to each charged

 count, and the district court making findings to support the conviction—including a

 finding that “the plea of guilty is knowingly, voluntarily, and intelligently made with

 a full understanding of the nature of the charges, the consequences of the plea, and

 defendant’s constitutional rights.” (Id. at 49.) The court accepted the plea but

 deferred its decision on the stipulated sentence until the sentencing hearing, which

 was scheduled for February 3, 2020.

       On December 30, 2019—approximately two months after entering the guilty

 plea, but before sentencing—Mr. McIntosh filed a motion to withdraw his plea. He

 claimed that the plea was not “knowing” because he did not understand “that the

 Court had no authority to order a sentence below the stipulated twenty-five years,”

 and that it was not voluntary because “it was clear that [he] did not wish to enter plea

 of guilty” and “[t]he nature of the environment was such that Mr. McIntosh was

 unable to exercise his free will.” (R., vol. I at 63–64.) The district court denied this

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 motion, finding that Mr. McIntosh’s guilty plea was knowing and voluntary and as a

 result there was no “fair and just” reason to grant his request. (Id. at 124.)

       At sentencing, the district court accepted the plea agreement terms and

 sentenced Mr. McIntosh to 25 years’ imprisonment. This appeal followed,

 challenging both the district court’s initial acceptance of the plea and its subsequent

 denial of the motion to withdraw the plea.

                               II.    STANDARD OF REVIEW

       Challenges to the validity of a plea are generally reviewed de novo. United

 States v. Rollings, 751 F.3d 1183, 1191 (10th Cir. 2014). The government argues,

 however, that Mr. McIntosh failed properly to preserve his challenges to the plea’s

 validity, which would mean this court would apply a plain-error standard of review.

 See United States v. Perez-Perez, 992 F.3d 970, 974 (10th Cir. 2021). We disagree.

 Mr. McIntosh specifically claimed that his plea was not knowing and not voluntary in

 his motion to withdraw the plea below. In that motion, he supported his claims that

 the plea was not knowing by highlighting the statements that his “judgment” was not

 “right,” his “mental state of mind” was not “right,” and he did not “understand . . .

 what [was] really going on.” (R., vol. I at 83–84.) As for his claims of

 involuntariness, the motion noted the repeated conferences with the government

 during the hearing and argued that they were coercive.

       On appeal, Mr. McIntosh makes arguments that are substantially similar—if

 not identical—to his arguments below, asserting that the plea was not knowing and

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 not voluntary due to his “frail” mental state, which the district court inadequately

 explored, plus alleged coercion by the government. (Aplt. Br. at 14.) Though his

 appellate briefs may be more detailed than his motion to withdraw the plea, Mr.

 McIntosh’s arguments below nonetheless gave the district court ample opportunity to

 consider these issues—and the district court in fact did so in a thorough written

 opinion. This is sufficient to preserve Mr. McIntosh’s arguments. See United States

 v. Leffler, 942 F.3d 1192, 1196 (10th Cir. 2019) (noting that “a federal appellate

 court does not consider an issue not passed upon below” (emphasis added) (quoting

 Singleton v. Wulff, 428 U.S. 106, 120 (1976)).

       We will review de novo Mr. McIntosh’s claim that his guilty plea was not

 entered knowingly and voluntarily. United States v. Mitchell, 633 F.3d 997, 1002

 (10th Cir. 2011) (applying de novo review where the issue of “whether [the

 defendant’s] plea was knowing and voluntary was raised before the district court on

 multiple occasions”). 1

 1
  Mr. McIntosh also appealed the district court’s denial of his motion to withdraw his
 plea. That issue would be reviewed for an abuse of discretion, rather than de novo,
 because “[d]efendants do not have an absolute right to withdraw a guilty plea.”
 United States v. Siedlik, 231 F.3d 744, 748 (10th Cir. 2000). Additionally, in the
 context of motions to withdraw, “[t]he burden is on the defendant to establish a ‘fair
 and just reason’ for the withdrawal of the plea.” Id. (quoting United States v. Black,
 201 F.3d 1296, 1299 (10th Cir. 2000)). See also Fed. R. Crim. P. 11(d)(2)(B).
 However, the underlying issue of “whether the plea was knowing and voluntary” is
 one of the factors courts must consider “in deciding whether a defendant has met the
 burden of showing that the district court, in denying a motion to withdraw a plea,
 acted unjustly or unfairly.” Id. at 749. This factor is the only one addressed by Mr.
 McIntosh in his arguments regarding the motion to withdraw his plea. Because the
 “knowing and voluntary” requirement is constitutional, a district court abuses its
 discretion if it denies a motion to withdraw a plea that was not knowingly and
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                                     III.   DISCUSSION

       “The Due Process Clause of the Fourteenth Amendment requires that a

 defendant knowingly and voluntarily enter a plea of guilty.” Fields v. Gibson, 277

 F.3d 1203, 1212–13 (10th Cir. 2002). See also Brady v. United States, 397 U.S. 742,

 748 (1970). This means a defendant’s decision to plead guilty must be “deliberate

 and intelligent and chosen from available alternatives.” United States v. Libretti, 38

 F.3d 523, 529 (10th Cir. 1994), aff’d, 516 U.S. 29 (1995). In the first instance, the

 burden is on the sentencing court and the attorneys on both sides “to apprise the

 defendant of the consequences of the plea and ensure that it is voluntary. If these

 duties are not discharged, the defendant is not ‘fully aware’ of the consequences of

 the plea and it is therefore involuntary.” United States v. Williams, 919 F.2d 1451,

 1456 (10th Cir. 1990), cert. denied, 499 U.S. 968 (1991) (quoting Brady, 397 U.S. at

 755). Again, we assess de novo whether the district court and attorneys adequately

 performed those duties. Id. at 1455.

       The specific content of the district court’s duties in voluntariness

 determinations is governed by Federal Rule of Criminal Procedure 11(b), which

 requires among other things that the court “address the defendant personally in open

 court and determine that the plea is voluntary and did not result from force, threats,

 voluntarily entered. Consequently, our initial assessment of the constitutional
 validity of Mr. McIntosh’s plea will necessarily control the outcome of our review of
 the denial of the motion to withdraw, and so we will not separately address that
 secondary issue.
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 or promises (other than promises in a plea agreement).” Fed. R. Crim. P. 11(b)(1–2).

 See also Williams, 919 F.2d at 1456. Though not itself a constitutional mandate,

 “Rule 11 . . . is designed to assist the district judge in making the constitutionally

 required determination that a defendant’s guilty plea is truly voluntary” and “to

 produce a complete record at the time the plea is entered of the factors relevant to

 this voluntariness determination.” McCarthy v. United States, 394 U.S. 459, 465

 (1969).

       Mr. McIntosh makes two main arguments as to why his plea was not knowing

 and voluntary. First, he claims that his “plea was not intelligently and deliberately

 made, and the district court failed to ensure that he understood what he was doing

 when he entered the plea,” as evidenced by his statements at the beginning of the plea

 hearing of being off his medications, about which the district court failed to inquire

 fully. (Aplt. Br. at 10–11.) Second, he claims that his plea was involuntary because

 his “will was overcome by mental coercion” arising from the government and the

 district court’s conduct during the hearing. (Id. at 14.) We agree with his first

 argument, though not his second, and find that Mr. McIntosh’s statements about his

 medication and mental fitness—which the district court failed meaningfully to

 investigate—show that the plea was not knowing and voluntary in the absence of any

 adequate Rule 11 record to the contrary.

       To prove the invalidity of his plea, Mr. McIntosh points to several pieces of

 evidence. One is the fact that he changed his mind five times over the course of the

 plea hearing. But a district court does not have to reject a plea just because a

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  defendant is having trouble making up his mind. There is inherent angst in pleading

  guilty to a significant sentence. See Miles v. Dorsey, 61 F.3d 1459, 1470 (10th Cir.

  1995) (“Although deadlines, mental anguish, depression, and stress are inevitable

  hallmarks of pretrial plea discussions, such factors considered individually or in

  aggregate do not establish that Petitioner’s plea was involuntary.”). Mr. McIntosh’s

  flip-flopping here reflected that angst, not a lack of understanding of the plea’s

  consequences.

        A second defect targeted by Mr. McIntosh is the alleged coercion resulting

  from the two off-the-record conferences with the government. Again, we find no

  evidence that these conferences affected Mr. McIntosh to such an extent that they

  would “overbear[] the will of the defendant.” Brady, 397 U.S. at 750. Even an

  allegation that the defendant was “hounded, browbeaten and yelled at” by his own

  counsel urging him to accept a plea agreement is not sufficient to render a plea

  involuntary. United States v. Carr, 80 F.3d 413, 417 (10th Cir. 1996). As such, mere

  urging by the prosecutor (who the defendant knows to be in an adversarial position)

  in a plea discussion where defense counsel was present falls well short of coercion, if

  such urging even took place here—which, on the record, is speculative. Mr.

  McIntosh can point to no specific threats or statements made by the prosecution that

  would amount to “mental coercion,” and this court will not assume that such threats

  occurred.

        Third, Mr. McIntosh claims that “the district court added the weight of its

  opinion to the pressure exerted on Mr. McIntosh,” exacerbating coercion, by stating

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  that the plea agreement was “better” for Mr. McIntosh after Mr. McIntosh said he

  would take the deal. (Aplt. Br. at 15; R., vol. II, at 22.) But this court has held that

  the district court does not violate Rule 11 by “questioning the defendant regarding

  the terms, consequences, and acceptance of the plea agreement” or “providing the

  defendant with information relating to these matters” once the agreement’s complete

  terms have been presented in open court. United States v. Carver, 160 F.3d 1266,

  1269 (10th Cir. 1998).

         In Carver, the district court had made comments that “evidenced some

  frustration” in response to the defendant’s “vacillation” about whether or not he

  would accept a plea agreement, but this court nonetheless upheld the plea because

  “the judge’s comments were prompted by an attempt to resolve the inconsistent

  positions taken by the defendant during the sentencing hearing and were, if anything,

  related to defendant's consideration of whether or not to withdraw his already

  negotiated plea agreement.” Id. (emphasis in original). The same is true here—any

  statements by the district court about the plea were made after the agreement’s terms

  were agreed upon by the parties and presented to the court. Mr. McIntosh had already

  read and signed the written plea agreement before even entering the courtroom, and

  there was never any indication at that point that the terms of the agreement were up

  for revision.

         Further, the district court made clear throughout the plea hearing that Mr.

  McIntosh was free to go to trial without additional consequence. In United States v.

  Cano-Varela, this court found Rule 11 error where the district court told the

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  defendant at a status conference “that he would ‘be doing at least ten years in a

  federal penitentiary’ if he did not plead and was found guilty at trial, and that a post-

  trial ‘sentence will ... be a harsh one.’” 497 F.3d 1122, 1133 (10th Cir. 2007). The

  closest the district court came to such a statement here was its question, in response

  to one of Mr. McIntosh’s statements that he wanted to go to trial rather than plead,

  that “[y]ou know that whatever the government has told you about, you know, for 25

  years here, the government can go a lot further?” (R., vol. II at 40.) There are two

  important differences between this statement and that in Cano-Varela: first, the

  district court’s statements in Cano-Varela occurred during a status conference, well

  before the plea agreement had been entered or even finalized. Second, the Cano-

  Varela court expressly compared the post-plea sentence to a post-trial sentence and

  indicated certainly that the latter would be much higher. The district court here, in

  contrast, merely checked that Mr. McIntosh understood that the government had the

  option to seek a higher sentence at trial—it did not suggest whether the court itself

  would impose a “harsh[er] one.” There is no evidence that the court’s statements

  here gave Mr. McIntosh more information that he did not have as a result of his prior

  meetings with defense counsel and the government. Thus, the statements by the

  district court as to the wisdom of the plea agreement here could not have changed

  Mr. McIntosh’s risk/benefit calculus in accepting the agreement and so were not

  “coercive.”

        There is one, and only one, piece of evidence proffered by Mr. McIntosh that

  we view as significant in our analysis of whether his plea was knowingly,

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  intelligently, and voluntarily made. That is Mr. McIntosh’s statement at the

  beginning of the hearing that he had not been taking his medication and his judgment

  was not “right” as a result. (R., vol. II at 16.) The district court did not ask Mr.

  McIntosh any follow-up questions regarding the medication or underlying illness, or

  the effect on Mr. McIntosh of not taking his medication. As a result, the record does

  not reflect any additional details about the medication or the reason it was prescribed

  to Mr. McIntosh, if indeed it was, nor about Mr. McIntosh’s history with and need for

  that drug.

        Where the district court is made aware during a plea proceeding that a

  defendant may be experiencing the effects of a mental illness, it must take that fact

  into account in its voluntariness determination. See Gonzales v. Tafoya, 515 F.3d

  1097, 1118 (10th Cir. 2008) (“In evaluating challenges to guilty pleas, courts must

  occasionally assess a defendant’s contention that his mental illness rendered the plea

  invalid.”). The extent to which the claimed mental disorder affects voluntariness

  depends on the totality of the circumstances, and the district court’s response under

  Rule 11 must attend to the specifics of the defendant’s situation. See United States v.

  Tanner, 721 F.3d 1231, 1233 (10th Cir. 2013) (per curiam) (“Determining whether a

  defendant knowingly and voluntarily waived his rights is a question of law . . . that

  must be based on the particular facts and circumstances surrounding the case,

  including the background, experience, and conduct of the accused” (internal

  quotations and alterations omitted)). The question here, then, is how much the lack

  of medication impacted Mr. McIntosh’s ability knowingly and voluntarily to plead,

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  and whether the district court adequately considered that impact in accepting the

  plea.

          In the only two cases in this circuit considering a defendant’s claims that his

  guilty plea was invalid because he had not been taking his prescription medication,

  this court rejected the claims. Nicholls v. Bigelow, 558 F. App’x 778 (10th Cir.

  2014) (unpublished); United States v. Cardenas-Uriarte, 498 F. App’x 843 (10th Cir.

  2012) (unpublished). But in Nicholls, the defendant did not inform the trial court of

  the medication issue during the plea colloquy, raising it only after the fact. 558 F.

  App’x at 783. And in Cardenas-Uriarte, the district court asked about the

  medications during the plea hearing and the defendant stated that he deliberately

  chose not to take the medications that day to ensure he was clearheaded. 498 F.

  App’x at 845. Not so here, where Mr. McIntosh claimed at the hearing that he was

  being denied access to his medications and his judgment was impaired as a

  consequence, and the district court asked nothing further on the subject. 2

          We have more squarely addressed the voluntariness implications of a

  defendant’s statements that he was taking medications that may be affecting his

  judgment at plea hearing. In United States v. Browning, this court held that the

  district court sufficiently ensured the voluntariness of the defendant’s plea by

  confirming at the hearing that the two prescription medications the defendant was

  taking were “solely for treating ulcers and reducing pain” and the defendant “had

  2
   Even if these cases were more directly on point, “[u]npublished decisions are not
  precedential.” 10th Cir. R. 32.1.
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  never been treated for mental illness,” in addition to the district court asking if the

  medications “in any way affected [his] ability to think or comprehend” (to which the

  defendant said no) and whether there had been any changes in the defendant’s speech

  or actions due to the medication (to which defendant’s counsel answered no). 61

  F.3d 752, 754 (10th Cir. 1995). Browning clarified that just a few questions from the

  district court in response to a defendant’s claim that he is under the influence of

  medications can be enough to demonstrate voluntariness and satisfy Rule 11. 3 But

  while we have said that those questions are sufficient to ensure voluntariness, we

  have not determined whether they are also necessary to ensure voluntariness.

        Other circuits addressing the same question as Browning—that is, how much a

  district court must investigate “a defendant’s statement that he presently is or may be

  under the influence of medication” during a plea hearing—have held that at a

  minimum, “[d]istrict courts should ask about the types of drugs and whether

  the medications are affecting the defendant’s mental state.” United States v. Carter,

  795 F.3d 947, 952 (9th Cir. 2015). See also United States v. Yang Chia Tien, 720

  3
    This court has repeatedly rejected defendants’ claims that medications created
  voluntariness problems when the defendant failed to mention the medication or claim
  ill effects from it during the plea hearing itself—at least where there is no other
  evidence, direct or circumstantial, reasonably suggesting to the court that the drugs
  may be important to the voluntariness inquiry. See, e.g., United States v. McGiff, 85
  F.3d 641 (10th Cir. 1996) (unpublished); United States v. Coates, 483 F. App’x 488,
  495 (10th Cir. 2012) (unpublished); Freisinger v. Keith, 473 F. App’x 846, 848 (10th
  Cir. 2012) (unpublished). Those cases are inapposite, however, given that the
  question here is what the district court needed to do to confirm the plea’s validity
  when the defendant actually claimed mental impairment due to lack of medication at
  the hearing, not merely after the fact.
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  F.3d 464, 470 (2d Cir. 2013); United States v. Savinon-Acosta, 232 F.3d 265, 268

  (1st Cir. 2000); United States v. Damon, 191 F.3d 561, 565 (4th Cir. 1999); United

  States v. Cole, 813 F.2d 43, 46 (3d Cir. 1987). But “[i]n general, appellate courts

  have vacated pleas only when the district court failed completely to engage in any

  meaningful follow-up with a defendant.” Carter, 795 F.3d at 952.

        We think a similar approach is fitting for this analogous context, in which a

  defendant tells the district court that he has not been taking his medications and

  specifically indicates that the absence of those medications is impairing his judgment.

  The district court must ask some follow-up questions such as what the medications

  are, what conditions they treat, and how those conditions affect the defendant’s

  present mental state. Here, the district court asked no questions inquiring about the

  medication specifically. Consequently, it was never established that Mr. McIntosh

  entered his plea knowingly and voluntarily, and we must vacate his plea as invalid as

  a matter of due process.

        Neither the findings of an earlier competency evaluation nor the district

  court’s later questions about Mr. McIntosh’s mental state are sufficient to cure the

  voluntariness issue we have identified. The competency evaluation—which the

  district court ordered at the request of Mr. McIntosh’s counsel based on his past

  diagnoses of mental disorders—indicated that Mr. McIntosh was not presently

  suffering any disorder that would render him unable to understand the proceedings

  against him. But a competency evaluation is not a proxy for the voluntariness

  determination. Godinez v. Moran, 509 U.S. 389, 400 (1993); Allen v. Mullin, 368

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  F.3d 1220, 1240 (10th Cir. 2004) (“The competency inquiry focuses on a defendant’s

  ability to understand the proceedings; the ‘knowing and voluntary’ inquiry focuses on

  whether he in fact did understand the proceedings.” (citing Godinez, 509 U.S. at

  400)). The stakes are too different—in pleading guilty, the defendant is surrendering

  the procedural safeguards of trial that are designed to ensure a fair process for all

  defendants, including those who are mentally ill. See McCarthy, 394 U.S. at 466.

  The district court’s voluntariness determination requires confirmation of mental

  capacity greater than mere competency to stand trial in order to protect the due

  process rights of a defendant who is legally competent but nonetheless incapable of

  making a deliberate, intelligent, and voluntary choice to surrender his constitutional

  rights at the moment of his plea hearing. 4

        The district court’s generalized questions about Mr. McIntosh’s mental state

  during the colloquy were not sufficient to ensure that the plea was knowing and

  voluntary in light of Mr. McIntosh’s statement about the medication. While the

  district court did ask defense counsel for their thoughts immediately after Mr.

  McIntosh’s statement about the medication, counsel did not address the issue directly

  4
    We do not mean to imply that a defendant with a mental disorder—even a severe
  one—will be unable, as a matter of law, to enter a valid guilty plea. See Wolf v.
  United States, 430 F.2d 443, 445 (10th Cir. 1970) (“[T]he presence of some degree of
  mental disorder in the defendant does not necessarily mean that he is incompetent to
  knowingly and voluntarily enter a plea.”). We mean only to emphasize the need for
  the district court to investigate adequately a defendant’s professed mental impairment
  to ensure that a plea is truly voluntary and knowing. Asking a few follow-up
  questions when the defendant references medication that he should be taking, but is
  not taking at the time of the plea, is required to fill that crucial role.
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  and instead broadly stated that they didn’t “have any concerns in regard to

  competency” given the prior forensic evaluation. (R., vol. II at 18.) This follow-up

  was insufficient for two reasons. First, counsel addressed competency rather than

  voluntariness, which as we have said are different things. Second, Mr. McIntosh

  himself—not merely his counsel—needed to be asked to elaborate on how the lack of

  medication was affecting him, given that only he could give a personal account. See

  McCarthy, 394 U.S. at 465 (explaining that Rule 11 requires “court to address

  defendant personally” in order to “expose[] the defendant’s state of mind on the

  record”); United States v. Vera, 514 F.2d 102, 104 (5th Cir. 1975) (“[M]ere

  assurance of defense counsel is not sufficient” to ensure defendant’s understanding of

  charge against him at plea hearing). The district court’s other inquiries about Mr.

  McIntosh’s mental state came later in the plea colloquy, shortly after Mr. McIntosh

  had said he would take the deal the first time (but before he changed his mind the

  second time):

               THE COURT: All right. Have you been treated recently
               for any mental illness or addiction to narcotics of any
               kind?
               THE DEFENDANT: Yes.
               THE COURT: What was that?
               THE DEFENDANT: When I went for my evaluation.
               THE COURT: All right. But what did you get?
               THE DEFENDANT: I don’t know. They didn’t tell me.
               THE COURT: Who was that? The person that you’re
               talking about.
               THE DEFENDANT: I don’t—I don’t remember her name.
               ...
               THE COURT: All right. Are you currently under the
               influence of any drug, medication, or alcoholic beverage of
               any kind?

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               THE DEFENDANT: No.
               THE COURT: Do you suffer from any mental condition or
               disability that would prevent you from fully understanding
               the charges against you or the consequences of your guilty
               plea?
               THE DEFENDANT: No.
               THE COURT: All right. Is there any reason we should not
               go forward here today?
               THE DEFENDANT: No. 5

  (Id. at 24–25.)

        Mr. McIntosh also responded “yes” when asked later if he understood the plea

  agreement and its consequences. (Id. at 37–38.) It is true that Mr. McIntosh’s

  statement that he did not “suffer from any mental condition” affecting his

  understanding was in conflict with his prior assertion that his judgment was not right

  and that he had not received his medications. But the obviousness of that

  contradiction merely highlights the need for the district court to inquire further in

  order to decide which statement was the more accurate one. If anything, this

  inconsistent response should have alerted the district court of the need to ask more

  specific questions about the medication—particularly given Mr. McIntosh’s

  ambiguous answer about what treatment for mental illness he had previously received

  and should be receiving.

  5
    Had Mr. McIntosh not given the more precise and unsolicited statement earlier in
  the hearing that contradicted this assurance and suggested that he did have a mental
  disability hindering his understanding of the plea, this colloquy would have been
  sufficient to confirm that the plea was knowingly and voluntarily entered. See United
  States v. Tanner, 721 F.3d 1231, 1233–34 (10th Cir. 2013).
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         We generally accept a defendant’s in-court assurance that he understands a

  plea agreement and voluntarily accepts it. United States v. Sanchez-Leon, 764 F.3d

  1248, 1260 (10th Cir. 2014). However, that practice cannot excuse the court from

  exploring the validity of a specific assertion by a defendant that he is not thinking

  clearly because he is off his medications. If a defendant’s lack of essential medicines

  prevents him from voluntarily entering a plea, it would similarly cast doubt on his

  later assertion that he did voluntarily enter the plea.

         To be clear, we do not hold that a defendant’s specific statements about his

  mental capacity always trump the defendant’s responses to the district court’s general

  colloquy questions. The need to interrogate about such statements will be governed

  on a case-by-case basis. But here, Mr. McIntosh began his change-in-plea hearing by

  stating that he was not taking his medication and was mentally impaired as a result.

  The district court’s generalized (even boilerplate) inquiries into Mr. McIntosh’s

  mental state some time later in the hearing—after he had changed his mind several

  times—did not uncover any more details about this missing medication and so were

  not sufficient to ensure the plea was knowing and voluntary. 6

  6
    The dissent makes much of the fact that Mr. McIntosh raised a “long list of
  concerns” in addition to his missing medication, as he also complained about the
  length of the plea agreement sentence, the conditions at the jail, and the loyalty of his
  counsel. Dissent at 3–5. Of course displeasure with a sentence and conditions of
  confinement cannot invalidate a defendant’s knowing and voluntary plea. But Mr.
  McIntosh’s expressed unhappiness at a long sentence does not mean that his separate
  statement that he was off his medication and mentally unwell can be automatically
  dismissed as mere “malingering,” without further investigation by the district court.
  His statement about not taking medication is a specific assertion casting doubt on his
  mental fitness, and so the district court should have inquired more about it to resolve
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        In sum, the record indicates that Mr. McIntosh’s guilty plea was not

  established as knowing and voluntary as required by the Constitution because the

  district court did not at all address his specific claim that he was off his medication

  and his judgment was therefore impaired. “A guilty plea is void if it is not knowing

  and voluntary.” United States v. Gigley, 213 F.3d 509, 516 (10th Cir. 2000). As a

  result, the plea cannot stand and we must vacate the convictions that flowed from it.

  Because we find his plea invalid on these grounds, we need not consider Mr.

  McIntosh’s remaining arguments.

                                      IV.    CONCLUSION

        For the reasons stated above, Mr. McIntosh’s convictions are VACATED and

  the case REMANDED to the district court for proceedings consistent with this

  opinion.

  that doubt. We express no opinion on whether the district court could have
  reasonably found Mr. McIntosh’s first statements about his ability to plead
  disingenuous once it had asked him follow-up questions about his medication and the
  illness for which it was prescribed. It is the failure even to try to gather that
  information that invalidates Mr. McIntosh’s plea, as there is nothing in the record
  following up on Mr. McIntosh’s initial statement that he had not been taking his
  medication and his mental state was too unstable to enter a plea.
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  United States v. McIntosh, No. 20-5089.

  EID, Circuit Judge, dissenting:

         Today, the majority holds “it was never established that McIntosh entered his plea

  knowingly and voluntarily,” and thus, “we must vacate his plea as invalid as a matter of

  due process.” Maj. op. at 16. In arriving at this conclusion, the majority also announces

  a broad rule: “[where] a defendant tells the district court that he has not been taking his

  medications and specifically indicates that the absence of those medications is impairing

  his judgment,” “[t]he district court must ask some follow-up questions such as what the

  medications are, what conditions they treat, and how those conditions affect the

  defendant’s present mental state.” Id. Here, I dissent because I do not find support in our

  caselaw for the rule pronounced by the majority, and because I do not find that the

  absence of an immediate and direct inquiry rendered McIntosh’s plea involuntary or

  unknowing.

         One factor under the voluntariness inquiry is whether there was “an adequate

  Federal Rule of Criminal Procedure 11 colloquy.” United States v. Hahn, 359 F.3d 1315,

  1328 (10th Cir. 2004) (en banc) (per curiam); see United States v. Tanner, 721 F.3d 1231,

  1233 (10th Cir. 2013) (finding that a “properly conducted plea colloquy . . . will, in most

  cases, be conclusive”). As the majority notes, Rule 11 is not a constitutional mandate

  itself, though the rule provides additional framework outlining the duties of a district

  court in a voluntariness determination. See McCarthy v. United States, 394 U.S. 459, 465

  (1969); see also Fed. R. Crim. P. 11(b)(1–2) (stating that the Rule 11 colloquy requires

  the district court to “address the defendant personally in open court and determine that
Appellate Case: 20-5089      Document: 010110660067         Date Filed: 03/21/2022     Page: 23

  the plea is voluntary”). It is within this framework that the majority pronounces a broad

  rule requiring district courts to ask direct and specific follow-up questions whenever “a

  defendant tells the district court that he has not been taking his medications and

  specifically indicates that the absence of those medications is impairing his judgment.”

  Maj. op. at 16. However, I do not find that our caselaw requires that a district court take

  a more specific, direct, or immediate action in response to the particular circumstances

  before the court here.

         In support of its rule, the majority cites to United States v. Browning, 61 F.3d 752,

  754 (10th Cir. 1995). But in that case we found the court’s inquiry to be sufficient and

  the defendant’s plea to be voluntary, and the court’s actions in Browning are not far from

  what the district court did here. Just like in Browning, the court here immediately asked a

  series of questions to McIntosh’s attorneys which elicited an extended discussion about

  McIntosh’s understanding of the plea agreement, his concerns, and his overall

  competency. See R. Vol. II at 17–20, 25–26; see also Browning, 61 F.3d at 754 (finding

  that the court asked his counsel whether there had been any changes in the defendant’s

  speech or actions due to the medication). Even though the court did not immediately

  target McIntosh and ask about his comments relating to his medication, the court’s

  inquiry—which did occur immediately after McIntosh’s list of concerns—resulted in a

  robust discussion that focused on McIntosh’s mental state and his overall understanding.

         Additionally, similar to the court in Browning, the court here gave McIntosh

  additional time and then, in a plea colloquy prompted by McIntosh that took place

  immediately after that recess, it asked whether McIntosh was “currently under the

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  influence of any drug [or] medication,” and whether he “suffer[ed] from any mental

  condition or disability that would prevent [him] from fully understanding the charges . . .

  or the consequences of [his] guilty plea.” R. Vol. II at 25; see Browning, 61 F.3d at 754

  (finding that the court asked “whether the medication had in any way affected Mr.

  Browning’s ability to think”).

         Similar to our holding in Browning, and considering these facts, I do not find that

  “the district court failed completely to engage in a meaningful follow-up” with McIntosh.

  Maj. op. at 16 (quoting United States v. Carter, 795 F.3d 947, 952 (9th Cir. 2015).

  Although the court’s immediate follow-up may have lacked direct questions to McIntosh

  about his mental state and alleged lack of medication, the court’s general inquiry was an

  appropriate response to McIntosh’s long list of concerns, especially when coupled with

  its subsequent, extensive plea colloquy that did in fact ask McIntosh about his mental

  state, mental condition, and any influence of “any drug, medication, or alcohol.” R. Vol.

  II at 25.

         Next, shifting the focus from the district court to McIntosh’s mental state at the

  time of his plea, looking to “all of the relevant circumstances surrounding [the plea],” I

  find that McIntosh had a sufficient understanding to voluntarily and knowingly plead

  guilty. Brady, 397 U.S. at 748. First, while competency and voluntariness are not the

  same thing, these concepts involve a large amount of overlap, and the psychologist’s

  previous competency examination was relevant to McIntosh’s state of mind at the time of

  his plea. Dr. Danielle Powers, a licensed psychologist and forensic evaluator, evaluated

  McIntosh over the course of a month, administering several tests to assess McIntosh’s

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  memory impairment, self-reported psychiatric symptoms, and ability to understand legal

  proceedings. [R. Vol. IV at 21–22.] Powers concluded that McIntosh did not presently

  meet the diagnostic criteria for any mood, depressive, or psychiatric disorders, and found

  no evidence that McIntosh “could not assist his attorney with his defense, or [of] the

  presence of a mental disease or defect that render[ed] him unable to understand the nature

  and consequences of the proceeding against him.” R. Vol. II at 30–31. Instead, Powers

  “diagnosed him with substance abuse disorders and malingering,” or “feigning,” meaning

  Powers noted a belief that McIntosh was faking or exaggerating an illness or incapacity.1

  R. Vol. II at 18; maj. op. at 4.

         Second, on the day of his plea, McIntosh’s list of concerns was not simply that he

  was not thinking clearly and that he was not taking proper medication. On the one hand,

  McIntosh started his statement with an entirely different concern: “honestly I felt like it’s

  too much time in my opinion.” Id. at 19. In response to the court’s follow-up questions,

  this is exactly how McIntosh’s counsel framed the issue: “I think the real problem is what

  Mr. McIntosh said initially, which is, it’s a lot of time.” Id. at 19.

         On the other hand, immediately after his mental state comment, McIntosh said,

  “I’m all over the place. You know, I want to take the deal, I don’t want to take the deal.”

  Id. at 16. He continued, uninterrupted: “And another thing is, at the jail they sent me to I

  have no access to no law library and I have, you know, limited phone calls . . . .” Id.

         1
           Malingering is diagnosed when the essential feature is the intentional production
  of “false or grossly exaggerated physical or psychological symptoms,” motivated by
  external incentives such as evading criminal prosecution. Diagnostic and Statistical
  Manual of Mental Disorders, Fifth Edition (DSM-5).
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  After the court momentarily confirmed which jail he was referring to, McIntosh went on:

  “They don’t even provide you like underwear or socks . . . . I also kind of feel like . . . I

  just don’t feel like my lawyer is really working for me. I feel like he’s working against

  me.” Id. at 17.

         When considered all together, these facts show it was possible that McIntosh’s

  comment was just more of the malingering he previously displayed in his medical

  examination, especially considering the understandably heavy decision he had to make.

  McIntosh’s long list of concerns seem to point towards the idea that he was scrambling to

  buy more time to make a decision on his plea, and that his main concern was that he did

  not like the amount of time that was being offered by the government. Surely, this is not

  to say that the district court could not have thought otherwise. But, looking to the totality

  of the circumstances, I cannot find that McIntosh’s comment was so egregious as to

  dismantle the voluntariness of his plea, or require that the court halt its general concerns

  or inquiries and direct its attention to one line in McIntosh’s larger statement.

         Even after McIntosh’s list of concerns, McIntosh’s two attorneys told the district

  court that McIntosh was competent to make this decision. Directly after McIntosh’s

  comments, the court noted that “it seems to me that he needs some [more] time,” and then

  asked Ms. Gullekson, one of McIntosh’s lawyers, what she thought. Id. at 17. That

  lawyer told the court that she was there when they “went over the terms of the plea

  agreement, the charges . . . , the potential ranges of punishment, the trial rights, and the

  deal,” and that she believed McIntosh “did have a basic understanding of it.” Id. at 17–

  18. At this point, the court turned to Mr. Widell, McIntosh’s other lawyer, who told the

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  court, given the fact that the case began with a psychological evaluation, he did not have

  “any concerns in regard to competency,” and that the report stated “no concerns . . .

  regarding competency.” Id. at 18. Even after the plea colloquy, the court again asked

  Gullekson whether she believed McIntosh was “in possession of his faculties and [was]

  competent to proceed,” to which she responded, “Yes.” Id. at 25–26.

         Finally, it is also of no small consequence that McIntosh himself assured the court,

  under oath, that he knowingly and voluntarily wanted to plead guilty. See Blackledge v.

  Allison, 431 U.S. 63, 73–74 (1977) (“Solemn declarations in open court carry a strong

  presumption of verity.”). The essence of the plea colloquy is to ensure the voluntary and

  knowing state of the defendant, and that is precisely what the district court offered

  McIntosh. See McCarthy, 394 U.S. at 465 (“By personally interrogating the defendant,

  not only will the judge be better able to ascertain the plea’s voluntariness, but he also will

  develop a more complete record to support his determination in a subsequent post-

  conviction attack.”); Tanner, 721 F.3d at 1233–34 (“A properly conducted plea colloquy,

  particularly one containing express findings, will, in most cases, be conclusive on the

  waiver issue, in spite of a defendant’s post hoc assertions to the contrary.”).

         Upon returning from recess, as the district court started to ask counsel a question,

  McIntosh independently spoke up, telling the court he wanted to “take the deal.” Id. at

  24. Moments later, after the court made sure it understood his intent, the court began its

  plea colloquy with McIntosh. During the colloquy, the court asked whether McIntosh

  was “currently under the influence of any drug [or] medication.” R. Vol. II at 25.

  McIntosh said, “No.” Id. The court asked, “Do you suffer from any mental condition or

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  disability that would prevent you from fully understanding the charges against you or the

  consequences of your guilty plea?” McIntosh responded, “No.” Id. The court also asked

  McIntosh whether he had been treated for any mental illness, and McIntosh responded,

  “Yes,” though he “didn’t know” what the mental illness was that he was treated for. Id.

  at 24. Finally, the court asked, “Is there any reason we should not go forward here

  today?” Id. McIntosh responded, “No.” Id.

         Overall, the colloquy covered McIntosh’s mental state at the time of the hearing,

  his mental condition, the influence of any drugs or medication on that mental condition,

  and his understanding of the consequences of his plea. Taken together with the

  surrounding circumstances, the court’s questions and McIntosh’s answers demonstrated

  that McIntosh’s plea was knowing and voluntary. This is true even where McIntosh

  initially stated that one of his concerns was he felt like his “mental state of mind [was]n’t

  right” and that the jail had taken him off medication. Id. at 16.

         Therefore, I believe the totality of the circumstances show that McIntosh

  knowingly and voluntarily entered into his guilty plea. Considering the context of

  McIntosh’s list of concerns, his two attorneys’ statements, and McIntosh’s own

  statements to the court, I believe there is enough evidence to show that McIntosh

  understood what was going on, including the consequences of his guilty plea, and

  voluntarily plead guilty.

         Respectfully, I dissent.

                                                7