Judge Auntie Says
Meet Judge Auntie™

The Honorable
Eileen A. Olds (Ret.)

A retired judge with a courtroom's discipline and a family kitchen's warmth.

Judge Eileen Olds

Judge Eileen Anita Olds is a proud graduate of Indian River High School, Chesapeake, Virginia. She received a Bachelor of Arts degree with distinction from the University of Virginia, and a Juris Doctorate degree from William and Mary Law School. Her exceptional legal career began as a private practitioner, specializing in state and federal criminal defense, and domestic relations law. In addition, she was appointed by two Attorneys General to represent the State Department of Highways and Transportation, and served as a Divorce Commissioner, and Commissioner in Chancery prior to her tenure on the bench.

Judge Olds' 1995 appointment to the bench was historical in that 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.

Her civic and professional affiliations include Delta Sigma Theta Sorority, Inc., the Links, Inc., and the Girl Friends, Inc. She is co-founder of the Friends of Hampton Roads, Inc., and a founder of the Williamsburg, VA Alumnae Chapter of Delta Sigma Theta Sorority. She has consistently been a member of local, state and national bar and judicial organizations and served on the Executive Board of the National Bar Association Judicial Council, and on the Executive Committee of the District Court Judges in Virginia.

In 2007, she was elected President of the American Judges Association (AJA) — the largest independent association of judges throughout the United States and Canada, and remains the first and only Virginian to hold the position since AJA's inception in 1959. She was inducted into Omicron Delta Kappa Honor Society as a Distinguished William and Mary Alumna. She is also the recipient of the Douglas Morton Alumni Service Award from the College of William and Mary.

Previously, she extended her community service on the Board of Directors of Job Corps, Inc., the Conference of Chief Justice's Best Practices Institute, and on the Virginia Task Force on Gangs and Youth Violence. In addition to her traditional court duties, Judge Olds was the visionary behind the implementation of a Truancy Court, designed to foster the importance of education. She has been recognized by numerous organizations, churches, and educational institutions for her advocacy and dedication to youth.

Judge Olds is the recipient of many awards and citations from distinguished organizations including Delta Sigma Theta Sorority, Inc., Phi Delta Kappa Sorority, Inc., and Zeta Phi Beta Sorority, Inc.; the United Negro College Fund; the Conference of Minority Public Administrators; the American Judges Association; USAA; the Virginia Desert Conference of Courts; Daughters of Isis; the City of Chesapeake; Tidewater Community College; and was previously designated as a Tazewell-Taylor Jurist-in-Residence at William and Mary Law School. She has been awarded the Thurgood Marshall Award from the National Bar Association Judicial Council, the Outstanding Jurist Award from the National Association of Women Judges, the Raymond Pace Alexander Award from the National Bar Association, the Woman of Achievement Award from the Miss Chesapeake/Miss America Pageant, and the Outstanding Virginian Award from the American Legion Auxiliary. She has also been honored and recognized for her public service by the Norfolk (VA) Navy Public Works Center, the United States Navy Military Sealift Command, the Atlantic Fleet's Commander Combat Logistics Group, and as a member of the Council on Legal Education's Hall of Fame.

Following twenty-four years of service, she retired on July 1, 2019. At the time of her retirement, she was Chesapeake's longest serving judge. She is the author of "Twin Expectations: raising the bar, raising expectations, raising children!" and has been featured in other periodicals and publications.

Since her retirement, she has served on the boards of WHRO Public Media, the Philanthropy Council of the Children's Hospital of the King's Daughters, and the Alumni Association Board of Directors at William and Mary Law School. She currently serves as a recall judge by appointment of the Chief Justice of Virginia.

In October 2021, the Chesapeake, Virginia City Council voted unanimously to name the acreage that includes the judicial system buildings and city hall the JUDGE EILEEN OLDS COURTYARD PARK.
Mentorship

Pouring into the Next Generation.

Long before the bench, and long after the gavel came down, Judge Olds has made room at the table for young people. From the Truancy Court she implemented in 2000 to Delta Sigma Theta youth initiatives, school visits, and quiet one-on-one conversations with children navigating hard seasons — mentorship has always been part of her calling. These are a few moments from that work.

Civics field trip · Students in Judge Olds' courtroom
Civics field trip · Students in Judge Olds' courtroom
A moment with the next generation
A moment with the next generation
Mentoring and encouragement
Mentoring and encouragement
Pouring into young scholars
Pouring into young scholars
Youth gathering · With Judge Auntie™
Youth gathering · With Judge Auntie™
Walking alongside the next generation
Walking alongside the next generation
Official courthouse portrait of the Honorable Eileen A. Olds
Official portrait, Circuit Court of Chesapeake, VA
On the Wall of the Bench

Her portrait now hangs
in the very court she served.

After more than two decades on the bench, Judge Olds' official oil portrait was unveiled at the Chesapeake courthouse — a permanent seat in the room even after retirement. Watch the ceremony and her remarks below.

Speaking Highlights

Come sit — she's been on every stage.

Keynotes, community halls, and outdoor addresses across Virginia and beyond. A short gallery from recent speaking engagements.

Outdoor address · Chesapeake, VA
Outdoor address · Chesapeake, VA
Keynote · Chesapeake Conference Center
Keynote · Chesapeake Conference Center
Community talk · Local library
Community talk · Local library
Fireside · Congregation hall
Fireside · Congregation hall
In the Community

A courtyard named for her — a legacy still being written.

Courtyard ParkRibbon cuttingSpeaking