US v. Carthorne: In 2010 Carthorne pleaded guilty to drug and gun charges and was determined, in the PSR, to be a career offender based on a Virginia conviction for assault and battery against a police officer. Trial counsel didn't object to the classification of that offense as a crime of violence or Carthorne's designation as a career offender. He explained at sentencing that he had "labored over that case long" and asked "providence for a lucky break," but conceded that he couldn't find anything to support an argument that Carthorne wasn't a career offender. Counsel admitted "I'm not a good lawyer" and went on to argue for a variance based on the facts of the actual prior offense - Carthorne spit at a cop. The district court varied slightly and imposed a sentence of 300 months, 89 months higher than the top of the non-enhanced Guideline range.
Carthorne appealed his career offender designation, but was stuck with plain error review. The Fourth Circuit affirmed, finding that the Virginia prior was not a crime of violence, and thus there was an error, but that the error was not plain because existing precedent didn't require that result. Carthorne then filed a 2255 motion alleging that his trial counsel had been ineffective for failing to object to the career offender designation on the ground that his prior conviction wasn't a crime of violence. The district court denied the motion. While Carthorne could easily show prejudice - had he been on de novo review on appeal he would have prevailed - the court concluded that he could not show that his counsel's performance had been deficient "essentially for the same reasons that the Fourth Circuit found not plain (i.e., obvious) error on direct appeal."
On appeal the Fourth Circuit reversed the denial of Carthorne's 2255 motion. The court concluded that the plain error standard and the Strickland ineffective assistance standard are fundamentally different and based in different sources - Federal rules and the Sixth Amendment, respectively. Therefore, they serve "different, yet complementary, purposes" and involve different variants of prejudice. While plain error looks only to settled law, effective assistance of counsel frequently requires "that counsel raise material issues even in the absence of decisive precedent." At the time of Carthorne's original sentencing although there was no precedent directly on point there were cases that "strongly suggested at the time that [the offense] did not qualify as a crime of violence." The sentencing transcript showed that counsel didn't really understand the crime of violence analysis and there was no strategic reason for failing to make an objection to the career offender determination. Therefore, Carthorne had demonstrated deficient performance of counsel, as well as prejudice, and was entitled to be resentenced.