United States v. Sherif Akande, 956 F.3d 257

Background

Sherif Akande was indicted for bank-fraud conspiracy and moved to suppress evidence seized from his home; the district court denied suppression.
Akande entered an open guilty plea (no plea agreement) after a standard plea colloquy and later sought to withdraw the plea.
Plea counsel admitted she misadvised Akande that an open plea would preserve his right to appeal the pretrial suppression ruling; in truth, only going to trial or entering a conditional plea could preserve that challenge.
Counsel filed to withdraw the plea; the district court denied acceptance-of-responsibility credit, sentenced Akande to 199 months, and Akande’s direct appeal of sentence was affirmed.
Akande brought a §2255 ineffective-assistance claim; the district court denied it without a hearing.
The Fourth Circuit reversed, holding counsel’s misadvice was not cured by the plea colloquy and that Akande showed prejudice because preserving appellate review was his principal objective and he likely would have insisted on trial if properly advised.

Issues

Issue	Akande's Argument	Government's Argument	Held
Whether counsel’s erroneous advice that an open plea would preserve appeal of the suppression ruling violated the Sixth Amendment	Counsel told Akande an open plea would preserve appellate rights; this misadvice induced the plea	Government largely conceded deficiency but argued any error was cured by the plea colloquy and that Akande was not prejudiced	Court treated performance as deficient (Government did not meaningfully dispute) and moved to prejudice analysis
Whether the district court’s plea colloquy cured counsel’s misadvice	Akande: colloquy was too general to correct counsel’s specific misstatement about preserving suppression-appeal rights	Government: the colloquy’s warnings about rights and appeals dispelled the misapprehension	Held: colloquy was too general and did not specifically address preservation of pretrial suppression appeals, so it did not cure the error
Whether Akande showed prejudice (would have gone to trial)	Preserving appellate review was his top strategic priority; contemporaneous evidence (discussions with counsel, call after plea) shows he valued appeal rights and likely would have insisted on trial if correctly advised	Government argued lack of prejudice and pointed to later procedural choices (e.g., withdrawing motion to withdraw plea)	Held: Akande established a reasonable probability he would have gone to trial to preserve appellate rights, satisfying prejudice under Lee v. United States
Whether Akande’s later withdrawal of his motion to withdraw the plea bars §2255 relief	Akande: later tactical choices do not erase his contemporaneous decisionmaking defect caused by misadvice	Government: argued those later actions undermine his claim of prejudice	Held: later withdrawal does not preclude showing prejudice as to the initial decision to plead; Lee controls focus on contemporaneous decisional calculus

Key Cases Cited

Tollett v. Henderson, 411 U.S. 258 (a guilty plea generally forfeits appeal of pretrial constitutional claims)
Strickland v. Washington, 466 U.S. 668 (ineffective-assistance framework: deficiency and prejudice)
Lee v. United States, 137 S. Ct. 1958 (prejudice when counsel’s error causes defendant to accept plea rather than go to trial; focus on defendant’s decisionmaking)
Garza v. Idaho, 139 S. Ct. 738 (restoration of appellate rights for ineffective assistance need not show appeal would have succeeded)
United States v. Akinsade, 686 F.3d 248 (district-court admonishment can cure counsel misadvice only if it carefully addresses the specific misadvice)
United States v. Foster, 68 F.3d 86 (example where colloquy cured erroneous sentencing advice because it specifically addressed maximum penalties)
United States v. Murillo, 927 F.3d 808 (colloquy warning too general to cure counsel’s misadvice)
United States v. Swaby, 855 F.3d 233 (prejudice may be shown by reasonable likelihood defendant would have gone to trial)