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Tenth Circuit: Guilty Plea Not Knowing and Voluntary Because Sentencing Court Failed to Ask Follow Up Questions After Defendant Said He’s Off His Medication and ‘Mind Isn’t Right’

by David M. Reutter

The U.S. Court of Appeals for the Tenth Circuit vacated a defendant’s guilty plea after finding the U.S. District Court for the Northern District of Oklahoma failed to ensure that his plea was knowingly and voluntarily made.

John Michael McIntosh pleaded guilty to five counts of Hobbs Act robbery and three counts of brandishing a firearm during the robberies. The charges were based on allegations that McIntosh robbed five Oklahoma convenience stores over a six-day period in February 2019. In return for his plea, the Government agreed to dismiss two counts of brandishing a firearm and that McIntosh be sentenced to 300 months in prison.

At his November 1, 2019, change-in-plea hearing, McIntosh voiced doubts about the agreement. In addition to stating it was “too much time,” he said he had been taken off his medication. As a result, he felt like his  “mental state of mind isn’t right to take anything right now because I don’t understand, you know, what’s really going on.”

The district court granted a recess, and defense counsel and the Government spoke to McIntosh about the plea agreement. Upon returning from recess, McIntosh said he would “just take the deal.” After the court started to discuss the rights McIntosh was waiving and the precise terms of the deal, McIntosh asked to speak to his attorney and expressed thereafter that he wanted to go to trial.

In response, the court said,  “All right. You understand the difference?... You know that whatever the government has told you about, you know, for 25 years, the government can go a lot further?” McIntosh said he understood and wanted a trial. The Government asked to speak to McIntosh off the record, and another recess ensued.

After that second conference, McIntosh again indicated he wanted to accept the plea agreement. The court then accepted his plea and deferred sentencing. About two months later, McIntosh filed a motion to withdraw his plea, arguing it was not knowingly and voluntarily entered. The district court denied the motion and sentenced McIntosh to 25 years’ imprisonment. McIntosh appealed.

On appeal, McIntosh argued his plea was not intelligently and knowingly made. He also argued “his will was overcome by mental coercion” from the Government’s conduct during the plea hearing.

The Court noted that the Due Process Clause of the Fourteenth Amendment requires that a guilty plea must be made “knowingly and voluntarily.” Fields v. Gibson, 277 F.3d 1203 (10th Cir. 2002); see Brady v. United States, 397 U.S. 742 (1970). This requires the defendant’s decision to be “deliberate and intelligent and chosen from available alternatives.” United States v. Libretti, 38 F.3d 523 (10th Cir. 1994), aff’d, 516 U.S. 29 (1995). The sentencing court and attorneys have the burden “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 (10th Cir. 1990).

The Court stated that Federal Rule of Criminal Procedure 11(b) governs the sentencing court’s duties with respect to voluntariness determinations, which requires, inter alia, the court to “address the defendant personally in open court and determine that the plea is voluntary and did not result from force, threats, or promises (other than promises in a plea agreement).” Rule(b)(1-2).

In attempting to prove the invalidity of his plea, McIntosh pointed to several pieces of evidence. First, he pointed to the fact that he changed his mind five times over the course of the plea hearing. The Court rejected that argument, stating angst is inherent in pleading guilty to a significant sentence. Miles v. Dorsey, 61 F.3d. 1459 (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.”).

The Court also found there was no coercion because McIntosh could point to no specific threats or comments by the prosecutor to support the claim. It further found the district court’s comments did not threaten a more severe sentence; it only assured McIntosh understood the Government’s options after a trial. The district court made it clear he was free to go to trial, and it never implied it would impose a more severe sentence after a trial, the Court stated. 

The Court, however, found error in the district court’s failure to conduct “follow-up questions regarding the medication or underlying illness, or the effect on Mr. McIntosh of not taking his medication.” As a result, there’s nothing in the record regarding additional details about the medication or why it was prescribed, the Court stated.

“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,” the Court stated. See Gonzales v. Tafoya, 515 F.3d 1097 (10th Cir. 2008). The Court added that the degree to which the alleged mental disorder affects voluntariness depends on the totality of the circumstances, and the district court’s inquiry under Rule 11 must address the specifics of the defendant’s situation. United States v. Tanner, 721 F.3d 1231 (10th Cir. 2013).

The question that was left unanswered by the district court was how much the lack of medication impacted McIntosh’s ability to knowingly and voluntarily plead. After McIntosh advised that he was denied his medication and that his judgement was impaired,  “The district court asked nothing further on the subject.”

The Government noted McIntosh was found by an evaluation to be competent to stand trial. However, the Court countered that a “district court’s voluntariness determination requires confirmation of mental capacity greater than mere competency to stand trial 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.”

The Court concluded that the district court’s generalized questions during the plea colloquy were insufficient to establish McIntosh’s plea was knowingly and voluntarily entered in light of his statements about his medication. “A guilty plea is void if it is not knowing and voluntary.” United States v. Gigley, 213 F.3d 509 (10th Cir. 2000). The Court instructed that “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 mental state.” Thus, the Court held that McIntosh’s plea was not knowing and voluntary as required by the Constitution.

Accordingly, the Court vacated McIntosh’s conviction and remanded for further proceedings consistent with this opinion. See: United States v. McIntosh, 29 F.4th 648 (10th Cir. 2022). 

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Related legal cases

United States v. McIntosh

Brady v. U.S.

397 U.S. 742; 90 S. Ct. 1463; 25 L. Ed. 2d 747


No. 270

November 18, 1969, Argued

May 4, 1970, Decided



DISPOSITION: 404 F.2d 601, affirmed.


Petitioner was indicted in 1959 for kidnaping and not liberating the victim unharmed in violation of 18 U. S. C. § 1201 (a), which imposed a maximum penalty of death if the jury's verdict so recommended. Upon learning that his codefendant, who had confessed, would plead guilty and testify against him, petitioner changed his plea from not guilty to guilty. The trial judge accepted the plea after twice questioning petitioner (who was represented throughout by competent counsel) as to the voluntariness of his plea, and imposed sentence. In 1967, petitioner sought post-conviction relief, in part on the ground that § 1201 (a) operated to coerce his plea. The District Court, after hearing, denied relief, concluding that petitioner's plea was voluntary and had been induced, not by that statute, but by the development concerning his confederate. The Court of Appeals affirmed. Petitioner claims that United States v. Jackson, 390 U.S. 570 (1968), requires reversal of that holding. Held: On the record in this case there is no basis for disturbing the judgment of the courts below that petitioner's guilty plea was voluntary. Pp. 745-758.

(a) Though United States v. Jackson, supra, prohibits imposition of the death penalty under § 1201 (a), it does not hold that all guilty pleas encouraged by the fear of possible death are involuntary, nor does it invalidate such pleas whether involuntary or not. Pp. 745-748.

(b) A plea of guilty is not invalid merely because entered to avoid the possibility of the death penalty, and here petitioner's plea of guilty met the standard of voluntariness as it was made "by one fully aware of the direct consequences" of that plea. Pp. 749-755.

(c) Petitioner's plea, made after advice by competent counsel, was intelligently made, and the fact that petitioner did not anticipate United States v. Jackson, supra, does not impugn the truth or reliability of that plea. Pp. 756-758.

COUNSEL: Peter J. Adang, by appointment of the Court, 396 U.S. 809, argued the cause and filed a brief for petitioner.

Joseph J. Connolly argued the cause for the United States. With him on the brief were Solicitor General Griswold, Assistant Attorney General Wilson, Jerome M. Feit, and Marshall Tamor Golding.

JUDGES: Burger, Black, Douglas, Harlan, Brennan, Stewart, White, Marshall

OPINION: [*743] [***753] [**1466] MR. JUSTICE WHITE delivered the opinion of the Court.

In 1959, petitioner was charged with kidnaping in violation of 18 U. S. C. § 1201 (a). n1 Since the indictment charged that the victim of the kidnaping was not liberated unharmed, petitioner faced a maximum penalty of death if the verdict of the jury should so recommend. Petitioner, represented by competent counsel throughout, first elected to plead not guilty. Apparently because the trial judge was unwilling to try the case without a jury, petitioner made no serious attempt to reduce the possibility of a death penalty by waiving a jury trial. Upon learning that his codefendant, who had confessed to the authorities, would plead guilty and be available to testify against him, petitioner changed his plea to guilty. His plea was accepted after the trial judge twice questioned him as to the voluntariness of his plea. n2 [*744] Petitioner [***754] was sentenced to 50 years' imprisonment, later reduced to 30.

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n1 HN1"Whoever knowingly transports in interstate or foreign commerce, any person who has been unlawfully seized, confined, inveigled, decoyed, kidnaped, abducted, or carried away and held for ransom or reward or otherwise, except, in the case of a minor, by a parent thereof, shall be punished (1) by death if the kidnaped person has not been liberated unharmed, and if the verdict of the jury shall so recommend, or (2) by imprisonment for any term of years or for life, if the death penalty is not imposed."

n2 Eight days after petitioner pleaded guilty, he was brought before the court for sentencing. At that time, the court questioned petitioner for a second time about the voluntariness of his plea:

"THE COURT: . . . Having read the presentence report and the statement you made to the probation officer, I want to be certain that you know what you are doing and you did know when you entered a plea of guilty the other day. Do you want to let that plea of guilty stand, or do you want to withdraw it and plead not guilty?

"DEFENDANT BRADY: I want to let that plea stand, sir.

"THE COURT: You understand that in doing that you are admitting and confessing the truth of the charge contained in the indictment and that you enter a plea of guilty voluntarily, without persuasion, coercion of any kind? Is that right?

"DEFENDANT BRADY: Yes, your Honor.

"THE COURT: And you do do that?


"THE COURT: You plead guilty to the charge?

"DEFENDANT BRADY: Yes, I do." App. 29-30.

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In 1967, petitioner sought relief under 28 U. S. C. § 2255, claiming that his plea of guilty was not voluntarily given because § 1201 (a) operated to coerce his plea, because his counsel exerted impermissible pressure upon him, and because his plea was induced by representations with respect to reduction of sentence and clemency. It was also alleged that the [**1467] trial judge had not fully complied with Rule 11 of the Federal Rules of Criminal Procedure. n3

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n3 When petitioner pleaded guilty, Rule 11 read as follows:

"A defendant may plead not guilty, guilty or, with the consent of the court, nolo contendere. The court may refuse to accept a plea of guilty, and shall not accept the plea without first determining that the plea is made voluntarily with understanding of the nature of the charge. If a defendant refuses to plead or if the court refuses to accept a plea of guilty or if a defendant corporation fails to appear, the court shall enter a plea of not guilty."

Rule 11 was amended in 1966 and now reads as follows:

HN2"A defendant may plead not guilty, guilty or, with the consent of the court, nolo contendere. The court may refuse to accept a plea of guilty, and shall not accept such plea or a plea of nolo contendere without first addressing the defendant personally and determining that the plea is made voluntarily with understanding of the nature of the charge and the consequences of the plea. If a defendant refuses to plead or if the court refuses to accept a plea of guilty or if a defendant corporation fails to appear, the court shall enter a plea of not guilty. The court shall not enter a judgment upon a plea of guilty unless it is satisfied that there is a factual basis for the plea."

In McCarthy v. United States, 394 U.S. 459 (1969), we held that a failure to comply with Rule 11 required that a defendant who had pleaded guilty be allowed to plead anew. In Halliday v. United States, 394 U.S. 831 (1969), we held that the McCarthy rule should apply only in cases where the guilty plea was accepted after April 2, 1969, the date of the McCarthy decision.

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[*745] After a hearing, the District Court for the District of New Mexico denied relief. According to the District Court's findings, petitioner's counsel did not put impermissible pressure on petitioner to plead guilty and no representations were made with respect to a reduced sentence or clemency. The court held that § 1201 (a) was constitutional and found that petitioner decided to plead guilty when he learned that his codefendant was going to plead guilty: petitioner pleaded guilty "by reason of other matters and not by reason of the statute" or because of any acts of the trial judge. The court concluded that "the plea was voluntarily and knowingly made."

The Court of Appeals for the Tenth Circuit affirmed, determining that the District Court's findings were supported by substantial evidence and specifically approving the finding that petitioner's plea of guilty was voluntary. 404 F.2d 601 (1968). We granted certiorari, 395 U.S. 976 (1969), to consider the claim that the Court of Appeals was in error in not reaching a contrary result on the authority of this Court's decision in United States v. Jackson, 390 U.S. 570 (1968). We affirm.

[***755] I

In United States v. Jackson, supra, the defendants were indicted under § 1201 (a). The District Court dismissed the § 1201 (a) count of the indictment, holding [*746] the statute unconstitutional because it permitted imposition of the death sentence only upon a jury's recommendation and thereby made the risk of death the price of a jury trial. This Court held the statute valid, except for the death penalty provision; with respect to the latter, the Court agreed with the trial court "that the death penalty provision . . . imposes an impermissible burden upon the exercise of a constitutional right . . . ." 390 U.S., at 572. The problem was to determine "whether the Constitution permits the establishment of such a death penalty, applicable only to those defendants who assert the right to contest their guilt before a jury." 390 U.S., at 581. The inevitable effect of the provision was said to be to discourage assertion of the [**1468] Fifth Amendment right not to plead guilty and to deter exercise of the Sixth Amendment right to demand a jury trial. Because the legitimate goal of limiting the death penalty to cases in which a jury recommends it could be achieved without penalizing those defendants who plead not guilty and elect a jury trial, the death penalty provision "needlessly penalize[d] the assertion of a constitutional right," 390 U.S., at 583, and was therefore unconstitutional.

Since the "inevitable effect" of the death penalty provision of § 1201 (a) was said by the Court to be the needless encouragement of pleas of guilty and waivers of jury trial, Brady contends that Jackson requires the invalidation of every plea of guilty entered under that section, at least when the fear of death is shown to have been a factor in the plea. Petitioner, however, has read far too much into the Jackson opinion.

The Court made it clear in Jackson that it was not holding § 1201 (a) inherently coercive of guilty pleas: "the fact that the Federal Kidnaping Act tends to discourage defendants from insisting upon their innocence and demanding trial by jury hardly implies that [*747] every defendant who enters a guilty plea to a charge under the Act does so involuntarily." 390 U.S., at 583. Cited in support of this statement, 390 U.S., at 583 n. 25, was Laboy v. New Jersey, 266 F.Supp. 581 (D. C. N. J. 1967), where a plea of guilty (non vult) under a similar statute was sustained as voluntary in spite of the fact, as found by the District Court, that the defendant was greatly upset by the possibility of receiving the death penalty.

Moreover, the Court in Jackson rejected a suggestion that the death penalty provision of § 1201 (a) be saved by prohibiting in capital kidnaping cases all guilty pleas and jury waivers, "however clear [the defendants'] guilt and however strong their desire to acknowledge it in order to spare themselves and their families the spectacle and expense of protracted courtroom proceedings." "That jury waivers and guilty pleas may occasionally be rejected" was no ground for automatically rejecting all guilty pleas under the statute, for such a rule "would rob the criminal process of much of its flexibility." 390 U.S., at 584.


Plainly, it seems to us, Jackson ruled neither that all pleas of guilty encouraged by the fear of a possible death sentence are involuntary pleas nor that such encouraged pleas are invalid whether involuntary or not. Jackson prohibits the imposition of the death penalty under § 1201 (a), but that decision neither fashioned a new standard for judging the validity of guilty pleas nor mandated a new application of the test theretofore fashioned by courts and since reiterated that guilty pleas are valid if both "voluntary" and "intelligent." See Boykin v. Alabama, 395 U.S. 238, 242 (1969). n4

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n4 The requirement that a plea of guilty must be intelligent and voluntary to be valid has long been recognized. See nn. 5 and 6, infra. The new element added in Boykin was the requirement that the record must affirmatively disclose that a defendant who pleaded guilty entered his plea understandingly and voluntarily. This Court has not yet passed on the question of the retroactivity of this new requirement.

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That a guilty plea is a grave and solemn act to be accepted only with care and discernment has long been recognized. Central to the plea and the foundation for entering judgment against the defendant is the defendant's admission in open court that he committed the acts charged in the indictment. He thus stands as a witness against himself and he is shielded by the Fifth Amendment from being compelled to do [**1469] so -- hence the minimum requirement that his plea be the voluntary expression of his own choice. n5 But the plea is more than an admission of past conduct; it is the defendant's consent that judgment of conviction may be entered without a trial -- a waiver of his right to trial before a jury or a judge. HN4 Waivers of constitutional rights not only must be voluntary but must be knowing, intelligent acts done with sufficient awareness of the relevant circumstances and likely consequences. n6 On neither score was Brady's plea of guilty invalid.

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n5 Machibroda v. United States, 368 U.S. 487, 493 (1962); Waley v. Johnston, 316 U.S. 101, 104 (1942); Walker v. Johnston, 312 U.S. 275, 286 (1941); Chambers v. Florida, 309 U.S. 227 (1940); Kercheval v. United States, 274 U.S. 220, 223 (1927).

n6 See Brookhart v. Janis, 384 U.S. 1 (1966); Adams v. United States ex rel. McCann, 317 U.S. 269, 275 (1942); Johnson v. Zerbst, 304 U.S. 458, 464 (1938); Patton v. United States, 281 U.S. 276, 312 (1930).

Since an intelligent assessment of the relative advantages of pleading guilty is frequently impossible without the assistance of an attorney, this Court has scrutinized with special care pleas of guilty entered by defendants without the assistance of counsel and without a valid waiver of the right to counsel. See Pennsylvania ex rel. Herman v. Claudy, 350 U.S. 116 (1956); Von Moltke v. Gillies, 332 U.S. 708 and 727 (1948) (opinions of BLACK and Frankfurter, JJ.); Williams v. Kaiser, 323 U.S. 471 (1945). Since Gideon v. Wainwright, 372 U.S. 335 (1963), it has been clear that a guilty plea to a felony charge entered without counsel and without a waiver of counsel is invalid. See White v. Maryland, 373 U.S. 59 (1963); Arsenault v. Massachusetts, 393 U.S. 5 (1968).

The importance of assuring that a defendant does not plead guilty except with a full understanding of the charges against him and the possible consequences of his plea was at the heart of our recent decisions in McCarthy v. United States, supra, and Boykin v. Alabama, 395 U.S. 238 (1969). See nn. 3 and 4, supra.

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[*749] II


The trial judge in 1959 found the plea voluntary before accepting it; the District Court in 1968, after an evidentiary hearing, found that the plea was voluntarily made; the Court of Appeals specifically approved the finding of voluntariness. We see no reason on this record to disturb the judgment of those courts. Petitioner, advised by competent counsel, tendered his plea after his codefendant, who had already given a confession, determined to plead guilty and



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