Annapolis Mayor Jared Littmann Names City Manager and City Attorney for Appointment

Annapolis Mayor Jared Littmann has announced two key appointments to the City’s executive leadership team: 

• Yolanda L. Lewis, who brings more than 20 years of experience managing large-scale government operations, has been nominated for Annapolis City Manager, and

• Anthony Kupersmith, a highly regarded legal expert in land use and municipal law, has been named Annapolis City Attorney. 

Mayor Littmann will present the two appointments to the Annapolis City Council for confirmation at the Monday, April 13, 2026, meeting. 

City Manager: If confirmed, Yolanda Lewis will serve as the City’s chief administrative officer, overseeing eleven City Departments and the Office of City Manager. She comes to the City having served as the Chief Administrative Officer for Fulton County, Georgia, where she managed a $30 million budget and directed operations for a million residents. 

Lewis’ more recent work includes high-level roles at the Pew Charitable Trusts and Meadows Institute, where she advised elected officials on policy reform and system accountability. She holds a Master of Public Administration and has completed executive leadership training at Yale School of Management. 

For the City Manager position, the City used the municipal recruiting firm Strategic Government Resources to conduct a nationwide search.  

“I am very pleased with the outcome. Yolanda not only met all of my expectations, but in her interviews with the directors’ panel and City Council members, she was the stand-out candidate,” said Mayor Littmann. “One of her many strengths is her emotional intelligence and ability to be collaborative. We all saw a strategic thinker and partner who will help us reach our goals.” 

City Attorney: If confirmed, “Tony” Kupersmith will lead the Office of Law and oversee legal services for the City, including providing legal advice to City officials and employees, representing the City in civil litigation, and drafting and reviewing legislation, contracts, and policies. 

Kupersmith’s experience is a blend of public service and private practice. Previously the County Attorney for Talbot County, Maryland, he served as the chief legal advisor to the County Council and county boards and commissions. In private practice with the Annapolis firm of McAllister, DeTar, Showalter & Walker LLC, he has represented businesses, individuals, and nonprofits in land use, real estate, and environmental matters. 

A graduate of William and Mary Law School, Kupersmith clerked for Judge Broughton M. Earnest on the Circuit Court for Talbot County. He is an Annapolis resident. Kupersmith said that his connections to the Chesapeake Bay and prior local government experience inform his professional interests in land-use policy and municipal law. 

“In interviews with the selection panel, Tony’s approach stood out,” said Mayor Jared Littmann. “With his experience managing staff and working with elected officials, he has the potential to elevate the City of Annapolis Office of Law. I look forward to working with him.” 

Pending confirmation, Lewis’ first day will be May 21. She will earn an annual salary of $270,000. Mr. Kupersmith will begin May 7 and earn an annual salary of $185,000.