United States v. Jimmy Desotell, 929 F.3d 821

On May 30, 2017 Green Bay police found methamphetamine and a handgun in bags Desotell admitted owning after officers investigating a retail theft searched a vehicle; Desotell was not a theft suspect.
A grand jury indicted Desotell on conspiracy/possession with intent to distribute methamphetamine and a §924(c) firearms charge.
Desotell initially had a Federal Defender, then retained private counsel, moved to suppress the evidence, and delayed signing a plea while the motion was pending.
After the district court denied the suppression motion, Desotell signed a plea agreement that contained an express waiver of appeals of pretrial motions and pleaded guilty; the government withdrew an information that would have raised his mandatory minimum.
At the change-of-plea colloquy the court repeatedly told Desotell the waiver would bar appeal unless the waiver’s validity itself were preserved; Desotell acknowledged understanding and pleaded guilty.
On appeal Desotell challenged the suppression ruling, but his opening brief omitted any argument attacking the appeal waiver; the government raised waiver, and the court dismissed the appeal as waived.

Issue	Desotell's Argument	Government's Argument	Held
Whether Desotell can appeal denial of his suppression motion despite plea waiver	Waiver invalid/coerced because gov’t threatened higher mandatory sentence and earlier unsigned plea lacked waiver	Plea agreement clearly and knowingly waived appeals of pretrial motions; waiver bars review	Waiver is enforceable; appeal of suppression is barred
Whether counsel preserved a challenge to the waiver on appeal	Counsel told district court they intended to challenge waiver; opening brief omitted waiver issue	Failure to raise waiver in opening brief and failure to address waiver means waiver stands	Court treats omission as an independent waiver and rejects later attempt to litigate suppression
Whether the plea was knowing and voluntary under Rule 11 and contract principles	Plea involuntary because defendant coerced by sentencing threat and confusion over plea versions	Colloquy and written plea demonstrate Defendant knowingly and voluntarily waived rights; no agreement removing waiver	Plea was knowing and voluntary; waiver enforceable under contract principles
Whether the court should reach the Fourth Amendment suppression merits	Focus on suppression of search/detention merits	Government says merits barred by waiver	Court declines to reach merits and dismisses appeal as waived

Carroll v. Lynch, 698 F.3d 561 (7th Cir.) (reply-brief waiver rule)
United States v. Goodson, 544 F.3d 529 (3d Cir. 2008) (defendant need not raise waiver in opening brief until government invokes it)
United States v. Powers, 885 F.3d 728 (D.C. Cir. 2018) (same as Goodson)
United States v. Arroyo-Blas, 783 F.3d 361 (1st Cir. 2015) (expectation that counsel address appeal waivers head-on)
United States v. Cole, 569 F.3d 774 (7th Cir.) (defendant may waive right to appeal)
United States v. Worthen, 842 F.3d 552 (7th Cir.) (appeal waivers generally enforceable)
United States v. Kingcade, 562 F.3d 794 (7th Cir.) (conditional pleas must precisely identify preserved pretrial issues)
United States v. Class, 138 S. Ct. 798 (Supreme Court) (valid guilty plea precludes challenge to pre-plea government conduct)
Haring v. Prosise, 462 U.S. 306 (Supreme Court) (valid guilty plea eliminates meaningful opportunity to challenge admissibility of evidence)