United States v. McIntosh, 29 F.4th 648

McIntosh was charged with five Hobbs Act robberies (18 U.S.C. § 1951) and five § 924(c) brandishing counts; plea agreement resolved eight counts with a stipulated 25-year sentence.
Pretrial forensic evaluation diagnosed substance-abuse disorders and malingering but found McIntosh competent to stand trial.
At the change-of-plea hearing McIntosh repeatedly vacillated and stated he had been taken off medication and his judgment was not "right." The court recessed twice for off-the-record conferences with the government; McIntosh ultimately pleaded guilty after an on-the-record colloquy.
The district court did not ask targeted follow-up questions about what medication McIntosh had missed, what it treated, or how absence affected his capacity to decide to plead.
Two months later McIntosh moved to withdraw the plea claiming it was not knowing or voluntary; the district court denied the motion and sentenced him to 25 years.
The Tenth Circuit vacated the convictions and remanded, holding the plea was not shown to be knowingly and voluntarily entered because the court failed to meaningfully investigate McIntosh’s unambiguous statement that lack of medication impaired his judgment.

Issue	McIntosh's Argument	Government/District Court Argument	Held
Whether McIntosh’s plea was knowing and voluntary	His plea was not knowing or voluntary because he said at the hearing he hadn’t been taking prescribed medication and his judgment was impaired; the court failed to investigate that claim	The colloquy and prior competency evaluation sufficed; off-the-record conferences and court comments did not coerce the plea	Court: Vacated plea — the court’s failure to ask follow-up questions about the medication left voluntariness unresolved
Whether denial of motion to withdraw plea was an abuse of discretion	Denial was improper because the plea was constitutionally invalid	District court found plea knowing/voluntary and denied withdrawal as not a "fair and just" reason	Court: Because plea was invalid, denial was effectively erroneous; vacated convictions and remanded (district-court ruling not separately sustained)

Brady v. United States, 397 U.S. 742 (constitutional requirement that guilty plea be knowing and voluntary)
McCarthy v. United States, 394 U.S. 459 (Rule 11’s role in producing a record of voluntariness)
Godinez v. Moran, 509 U.S. 389 (competency vs. knowing-and-voluntary plea distinctions)
United States v. Browning, 61 F.3d 752 (few targeted questions about medication can suffice to ensure voluntariness)
United States v. Carter, 795 F.3d 947 (district courts should ask about drug type and effect when defendant says medication may affect mental state)
United States v. Tanner, 721 F.3d 1231 (voluntariness inquiry depends on totality of circumstances and colloquy)
United States v. Gigley, 213 F.3d 509 (guilty plea void if not knowing and voluntary)
United States v. Libretti, 38 F.3d 523 (plea must be deliberate and intelligent)
United States v. Carr, 80 F.3d 413 (strong urging by counsel or prosecutor short of coercion does not automatically render plea involuntary)
United States v. Cano-Varela, 497 F.3d 1122 (when court comments effectively threaten harsher post-trial sentence, may render plea involuntary)