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From the Bench to the Stage
Richmond’s historic judge always commands the spotlight
By Steve Clark
Courtroom drama and the drama of live theater.
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Roger L. Gregory has a passion for both.
His passion for courtroom drama comes with the job. He has been a federal judge with the 4th U.S. Circuit Court of Appeals for nine years. His passion for theatrical drama inspired him to become a stage actor at the age of 50.
Gregory’s appointment to the federal bench was a Christmas present from President Bill Clinton in 2000. Gregory, then a law partner with former Virginia Gov. L. Douglas Wilder, was having Christmas dinner with his wife and three daughters at their Richmond home when the telephone rang.
“The White House called, and I was told President Clinton was going to recess-appoint me,” the 56-year-old Gregory said in an interview in his office in the Lewis F. Powell Jr. U.S. Courthouse in downtown Richmond.
“Two days later, I’m in the White House in the Oval Office with the president.”
BOTH CLINTON AND BUSH
Six months earlier, Clinton, in the final days of his second term, had nominated Gregory to the appellate court. Gregory did not receive a hearing before the U.S. Senate, however, so Clinton used his authority to make a recess appointment when Congress was not in session.
Gregory took the oath of office Jan. 18, 2001. It was historic. He was the first African-American to serve as an appellate judge for the 4th Circuit, which is based in Richmond and hears appeals from trials in Virginia, West Virginia, Maryland and the two Carolinas. Circuit courts are just one level below the U.S. Supreme Court in the federal judiciary.
Two days later, President George W. Bush was sworn into office. Because Clinton is a Democrat and Bush a Republican, the question was: Would Bush renominate him?
“I had no assurances it would happen,” Gregory said. “I decided to concentrate on doing the best I could for the time I was there. I just pressed on.”
Virginia’s senators at that time were John Warner and George Allen, both Republicans. Both strongly supported Gregory. Bush renominated him in May and he was confirmed by the Senate on July 20, 2001 -- three days after his 48th birthday. The vote was 93-1. Once again, Gregory made history. He became the first (and remains the only) person to be nominated to the U.S. Court of Appeals by two presidents of different political parties.
A WIFELY NUDGE INTO ACTING
Gregory took up acting in the summer of 2003, thanks to his wife, Carla. She died last summer at age 53, nearly two years after being diagnosed with a malignant brain tumor.
“For my 50th birthday, she signed me up to audition for To Kill a Mockingbird at Barksdale Theatre,” Gregory said. “She said, ‘You’re always talking about acting; now go ahead and do it.’ So I auditioned and I got the part.”
He played Reverend Sykes, who is in the courtroom balcony with lawyer Atticus Finch’s two children during the trial of Tom Robinson.
Subsequent roles include one in Barksdale’s production of The Lark, a drama based on the life of Joan of Arc, and one in Fences at Petersburg’s Sycamore Rouge Theatre.
FROM PETERSBURG TO THE TAJ MAHAL
Gregory grew up in Petersburg, the adopted son and only child of George and Fannie Gregory. They are the main reason he became the man he is, Gregory said.
“I did not take being blessed with good parents lightly, because that is something not to be taken for granted,” he said. “They emphasized faith and family, commitment and hard work.”
Neither parent graduated from high school, but they knew the value of education. When Gregory was a schoolboy, his father bought a World Book encyclopedia set. “I traveled the world every day in those books. I remember reading about India and seeing a picture of the Taj Mahal. I must have looked at that picture a thousand times. Later in life, when I visited the Taj Mahal, I thought about my parents and that encyclopedia set.”
His father, who died in 1994, worked at Petersburg’s Brown & Williamson tobacco factory for about 40 years. “You can count on one hand how many days he missed work,” Gregory said. “He had a great work ethic.”
His mother, who died in 1998, worked at another tobacco factory during World War II. When the war ended, she was laid off and began working as a domestic. In the 1960s she was hired by Brown and Williamson. She retired from that company in 1985.
Petersburg’s public schools were segregated when Gregory was growing up. Before his senior year (1970-71), however, the city’s two high schools — all-black Peabody High and all-white Petersburg High — were merged.
“I was in the first graduating class at Petersburg High where there was one high school. It was easy when it came because the two schools were merged.”
For college he chose Virginia State University, where his mother had worked as a maid when she was a teenager. Thanks to Leon Hairston, his high school government teacher and Dr. Calvin Miller, chairman of the political science department at Virginia State, Gregory received an academic scholarship. He also held down expenses by living at home.
“Virginia State gave me opportunities that I never would have had the chance to do at any other place,“ he said. “Plus, I met my wife there.”
INSPIRED – AND INSPIRING
Virginia State also was where he met Doug Wilder, then a member of the Virginia Senate.
“Senator Wilder taught my constitutional law class. I would see him open his appointment book with his court dates. That was the inspiration for me to become a lawyer. Who would have thought that 10 years later we would be law partners?”
Gregory graduated from the University of Michigan’s law school in 1978, worked for a couple of years for a law firm in Detroit, and then accepted a job with Hunton and Williams in Richmond. He was mentored there by Lewis Booker, whom Gregory describes as “an incredible lawyer and a wonderful man.”
In 1982, Gregory and Wilder started their firm on Church Hill. With his lifetime appointment to the federal bench, Gregory resigned as managing partner.
Having been nurtured by so many positive role models, Gregory tries to have a positive influence on young people. For example, he mentors students at Armstrong High School in Richmond’s East End.
“I really believe that to those whom much has been given, much is required,” he said.
“I let young people come here to the court, and I let them sit in the judge’s chair. They need to see themselves as something else. They need to envision success.”

Steve Clark is a former columnist with the Richmond Times-Dispatch and, before that, The Richmond News Leader.
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