CHESAPEAKE — For decades, she has been “Your Honor,” but for many in Hampton Roads and beyond, Eileen Olds is Judge Auntie.
Olds, an iconic figure in the Hampton Roads legal system, was the first woman and first Black person to serve as a judge in the First Judicial District in Chesapeake. On Thursday, the city cemented her legacy at the Chesapeake Municipal Center. The large park at the center of the city’s court buildings has taken her name: Judge Eileen Olds Courtyard Park.
About 200 people gathered for the dedication ceremony — including city leaders, members of Congress, judges, law enforcement officials and faith leaders. Dozens of court staff, family, friends, neighbors and members of Delta Sigma Theta Sorority, Inc. also were there to support the occasion. The open space has been equipped with a large clock tower, seating areas, gardens and a large statue spelling “Love.” While working with the city on its design, Olds said she is excited to see the community gatherings that are to come.
The courtyard park at Chesapeake’s courthouse complex is named after long-time judge Eileen Olds on Thursday, Sept. 4, 2025. (Stephen M. Katz / The Virginian-Pilot)
“I smile when I think about the number of proposals and weddings that can take place in front of the ‘Love’ sign,” Olds said. “I think of parents who may have had to bring a small child to court exasperated, and then walks out of one of these buildings and gets a breath of fresh air. I think of people on the way to City Hall to transact business, and then pausing to recognize that it’s beautiful out here.
“I think of city workers who may enjoy their lunch under one of the shelters or on the park bench. I see churches, sororities and fraternities holding their events and family reunions.”
Olds first took the bench in 1995. Since then, she was has been elected as president of the American Judges Association and the South Hampton Roads Bar Association. She also served on the Virginia Commission for Women and Minorities in the legal profession and the Executive Board of the National Bar Association’s Judicial Council. She is a founder of the Friends of Hampton Roads, Inc. and the Williamsburg alumnae chapter of Delta Sigma Theta Sorority, Inc.
She retired in 2019, but she serves as a recall judge by appointment.
Valerie Brown, a friend for more than 50 years, said “Judge Auntie” is an apt description for Olds. Brown said she has an open ear and is a staunch advocate for her community. She even credits Olds with helping establish her private CPA practice by securing its location and helping build a network of clients.
Judge Eileen Olds gets a warm hug from a close friend during Thursday, Sept. 4, 2025, afternoon’s dedication ceremony. (Stephen M. Katz / The Virginian-Pilot)
“You can talk to her just like an auntie,” Brown said. “We all have that aunt — or wish we had that aunt — we could speak to and talk to about anything and everything, and there was no judgment. She would laugh with you, cry with you, comfort you, but when it was time to give the advice, she told you exactly what you needed to hear, not what you wanted to hear.”
Olds, who began her legal career in 1982, recalled the sexism and racism she faced during the early years. She said she was mistaken for a defendant, rejected from the Chesapeake Bar Association multiple times, and in one case, was told her heels did not fit the decorum of a courtroom. Olds also recalled when she could not use the lawyers’ bathroom at the courthouse because all the other attorneys were men.
She said she has since forgiven them.
Katherine Currin, a past president of the Chesapeake Bar Association, said Olds handled the struggles of integrating Chesapeake’s bench with grace.
“(Olds) was one of the judges that I appeared in front of on a regular basis, and it was wonderful to see a woman in the position looking back at me,” said Currin, recalling the beginning of her own legal career in the public defender’s office. “Only recently have we begun to understand the psychology of being the only person in the room that looks like you.”
Olds credited her parents, sisters and many others for her success. Through the years, many community members wrote letters and spoke before the City Council to create a monument or park in her honor. Growing up in Chesapeake, she said she wanted to “right some of the wrongs” that she saw in her community. Becoming an attorney and later, a judge, allowed her to do that.
“I heard so many stories about mistreatment in the criminal justice system and seeing people spinning their wheels wanting to do better, but they just didn’t have a chance,” Olds said. “I didn’t rely on the confidence in me — because quite honestly, even though it may have looked like it — sometimes I didn’t have it. So I didn’t rely on the confidence in me, but I relied on the confidence that God had in me.”
Eliza Noe, eliza.noe@virginiamedia.com
