US v. Whiteside: Whiteside was sentenced as a career offender based on a pair of North Carolina convictions. After Simmons, those convictions are no longer felonies. Whiteside filed a 2255 motion within a year after Simmons was decided seeking to vacate his sentence. The district court denied the motion, for various reasons. On appeal, a panel of the Fourth Circuit reversed, finding that Whiteside had not waived his right to file the motion, that it was timely because it was filed within a year of Simmons and, at any rate, equitable tolling applied. The panel also concluded that Whiteside prevailed on the merits and ordered his sentence vacated.
The Government sought rehearing and the full Fourth Circuit reversed the panel, affirming the denial of Whiteside's motion. In doing so, the en banc court (Judge Wilkinson writing the opinion) did not reach the merits, but concluded that Whiteside's motion was not timely filed. Although it was filed within a year of Simmons, the court concluded that Simmons only stated new law, and would not constitute a new "fact" which restarted the one-year statute of limitations in 2255. The court distinguished between a situation where a prior conviction itself was vacated - it's nonexistence is a "fact" - and a legal change that renders the still extant conviction different in kind. The en banc court also concluded that equitable tolling did not apply, noting that although it might have been futile for Whiteside to file a 2255 on these grounds before Simmons, other defendants had done so (Simmons, for one).
Judge Gregory dissented, joined by Judge Davis, arguing that the majority had misconstrued its ability to act equitably (in light of recent Supreme Court precedent) and that it "is simply unjust to deny someone the opportunity to receive a properly calculated sentence." He also argues that the majority places too much weight on concerns about finality, noting the recent waves of amendments to the Guidelines that have been made retroactive. Judge Wynn also dissented, arguing (by quoting Judge Wilkinson from 2012) that the opinion would "drive citizens to rub their eyes and scratch their heads" and that if the "objectively reasonable person on the street" was asked whether a court could fix this mistake the "response would be 'Of course. Why do you ask?'"