Roger L. Gregory invites visiting schoolchildren to sit in his judicial chair so they can, as he puts it, see what they might become. The setting carries its own history: his chambers are in a Richmond courthouse built three years before the Civil War began, a building that once housed an office of the president of the Confederacy. "Who would've thought that this little boy from Petersburg would be the first African American on this court, and its first African American chief judge?" he asked in a 2016 interview.
Gregory was born in Philadelphia on July 17, 1953, and raised in Petersburg, Virginia, by adoptive parents who both worked in a tobacco factory. "They got up early," he said, "so I could have more time to dream." He graduated summa cum laude from Virginia State College in 1975 and earned his law degree at Michigan in 1978, where he cited professors L. Hart Wright, Yale Kamisar, John Reed and J.J. White among those who influenced him most.
After working at the Detroit office of Butzel Long and the Richmond firm of Hunton & Williams, Gregory joined L. Douglas Wilder, who later became Virginia's governor, to form Wilder & Gregory in 1982. He served as managing partner and head of litigation until his appointment to the federal bench. Starting his own small practice in Virginia, he learned that his law school did not yet carry the same weight with some clients; he was glad, he said, for the chance to prove his skill and value to them. "It isn't about your rootage, it's about your fruitage."
President Bill Clinton nominated him to the Fourth Circuit in 2000, but the Senate declined to act, so Clinton appointed him during a congressional recess that December. "It is unconscionable that the Fourth Circuit has never had an African American appellate judge," Clinton said at the time. President George W. Bush renominated him in May 2001, and the Senate confirmed him that July on a near-unanimous vote. Gregory was the first African American judge to serve on the court, which covers Maryland, Virginia, West Virginia and the Carolinas. As chief judge from 2016 to 2023, he led the court's judges, chaired the circuit's judicial council and carried administrative responsibility for the federal courts across its five states.
