How do you celebrate a career of more than 20 years? For one local judge, having a park named in her honor is just one of many awards and accolades she has received in recognition of her years of hard work.
On Thursday, September 4, the City of Chesapeake dedicated the Judge Eileen Olds Courtyard Park during a moving ceremony that brought smiles, tears and the reunion of lifelong friends and colleagues.
Judge Eileen Olds, a Chesapeake native and a graduate of Indian River High School, is a trailblazer in her chosen career. She made history in 1995 when she became the first woman and African-American judge in the First Judicial District in Virginia. Prior to her judicial appointment, Judge Olds served as President of the South Hampton Roads Bar Association and on the Virginia Commission for Women and Minorities in the legal profession.
She began her legal career as a private practitioner, specializing in state and federal criminal defense and domestic relations law. While she encountered obstacles in what she described as “an all boys club,” at the time, she was determined to proceed. Her work helped pave the way for other young women seeking to practice law.
Katherine D. Currin, past president of the Chesapeake Bar Association, recalled her first day on the job as a public defender in Chesapeake. “It was wonderful to see a woman in your position looking back at me,” she said.
This sentiment was echoed by everyone who gave remarks during the ceremony.
Judge Olds had numerous friends, family and colleagues in attendance at the dedication — from high school friends, sorority sisters, former neighbors, mentors, co-workers, and even a former babysitter.
Judge Olds’ lifelong friend Valerie Brown, executive pastor emeritus at The Mount Global Fellowship of Churches, shared personal memories of her friend who was a cheerleader with her in high school. Judge Olds helped Brown get her business started when she returned to Chesapeake after some time away.
“She dragged me to networking events all over Hampton Roads and introduced me to people,” she recalled.
Brown also shared that Judge Olds--known by many as “Judge Auntie” because “you can talk to her just like an auntie”—is a woman of deep faith. She said she watched her friend live out that faith many times throughout her career.
“You have made such an impact on so many lives,” Chesapeake Mayor Rick West said in his remarks at the dedication ceremony. “You have kept our city safe.”
When Judge Olds addressed the crowd, she said she was incredibly grateful to everyone who came out to share her special day. From a young age, she said, she knew she wanted a career through which she could address some of the wrongs she saw around her playing out in the judicial system.
She also had an important message to all the naysayers and those who did not treat her as an equal in the courtroom. “You’re forgiven,” she told the crowd.
She acknowledged the important role her faith and her spiritual mentors played in advancing her career.
“I didn’t rely on the confidence I had in me,” she explained. “I relied on the confidence God had in me.”
When Judge Olds retired in 2019, she was Chesapeake’s longest-serving judge. Since her retirement, she has remained busy serving on the boards of local organizations — including WHRO Public Media’s board from 2019-2025.
“I hope in some small way to inspire others to walk the paths I’ve carved,” Judge Olds said. “But I hope it will be easier for them.”
She also acknowledged the community behind her achievements and thanked them for their support, especially the unwavering commitment of her twin sister Francine, who is a physician.
Their mother, who is now deceased, always told her children that she prayed they “would go far” Judge Olds told the crowd. As a child, she wondered what her mom meant. But in looking back over her career, she said she now understands.
“I believe her prayers were answered today.”
The Judge Eileen Olds Courtyard Park is located at 208 Conquest Way, behind City Hall in Chesapeake.