United States v. Charles Pittman, 125 F.4th 527

Charles Pittman pleaded guilty to aiding and abetting the arson of the Market House, a building owned by the City of Fayetteville, an institution receiving federal financial assistance, in violation of 18 U.S.C. § 844(f)(1) and (2).
Pittman confirmed his understanding of the charges and admitted committing acts that constituted the crime's elements during his plea hearing.
After pleading guilty but before sentencing, Pittman sought to dismiss Count 1, arguing the statute required a stronger connection between the building and federal funding and challenging the validity of his indictment.
Pittman did not move to withdraw his guilty plea but raised, for the first time, an as-applied constitutional challenge to the statute, claiming it was unconstitutional as applied to his conduct.
The district court rejected Pittman's arguments and sentenced him to 60 months of imprisonment.
On appeal, Pittman raised statutory interpretation and as-applied constitutional challenges to his conviction under § 844(f)(1).

Issue	Pittman's Argument	Government's Argument	Held
Does a guilty plea waive statutory interpretation?	Pittman argued statute doesn’t cover his conduct; thus, plea should not bar statutory argument.	Guilty plea is admission of facts constituting the crime; waiver applies to statutory claims.	Guilty plea waives arguments that conduct is not covered.
Timeliness of as-applied constitutional challenge	Raised constitutional issues after the plea, argued no forfeiture due to jurisdictional nature.	Argument forfeited unless timely raised in pretrial motion or good cause shown for delay.	Challenge forfeited; must be raised timely pretrial.
Whether plain error review provides relief	Statute’s application is clearly unconstitutional, justification is lacking.	No clear or obvious constitutional error in statute's application to facts of this case.	No plain error; constitutional claims fail.
Federal power over protected buildings	Lacks sufficient federal nexus for criminal authority under § 844(f)(1).	Market House historical registry and funding create sufficient federal interest/power.	Federal power adequate; statute constitutionally applied.

Class v. United States, 583 U.S. 174 (2018) (guilty plea does not bar constitutional challenges to statute, but does bar claims inconsistent with guilty plea admissions)
United States v. Cotton, 535 U.S. 625 (2002) (jurisdictional defects can be raised any time, but not all defects are truly jurisdictional)
United States v. Olano, 507 U.S. 725 (1993) (distinguishes waiver from forfeiture; outlines plain error review)
Puckett v. United States, 556 U.S. 129 (2009) (plain error must be clear or obvious to warrant relief)