Annapolis Mayoral Hopefuls Debate Less Than A Week Before Primary Election

By William J. Ford, Maryland Matters

September 11, 2025

With less than a week before the Annapolis primary election, Democratic mayoral candidates Rhonda Pindell Charles and Jared Littmann presented their cases during a debate Wednesday on why they should be the next mayor of Annapolis.

The winner in Tuesday’s primary election will face Republican Bob O’Shea, who has no primary challenger but still participated in Wednesday’s debate at the Boys and Girls Club of Annapolis. They are running to replace Mayor Gavin Buckley (D), who is term-limited after serving two four-year terms.

While he faces no primary challenge, O’Shea will face a challenge in the Nov. 4 general election in a city where registered Democratic voters outnumber Republicans by a more than 2-1 ratio.

“I believe that everybody should have an opportunity, and I also believe in tough love,” said O’Shea, a local businessman who ran unsuccessfully for mayor in 2013 and state delegate in 2018. “Tough love is something that when someone does something, you scare them a little bit to not do it again.”

While O’Shea announce this summer, Littman got an almost two-year head start on the race, announcing his candidacy in January 2024. Pindell Charles officially announced her candidacy in September of last year.

The debate, hosted by the nonpartisan Action Annapolis, provided the candidates with questions in advance on quality of life, housing and improvement of city services.

Different responses came up when all three candidates were asked: “As mayor, what would you do differently from current and past administrations?”

Attendees listen to the Annapolis mayoral debate between Democrats Rhonda Pindell Charles and Jared Littman and GOP candidate Bob O’Shea. (Photo by William J. Ford/Maryland Matters)

Littmann, a small business owner who manages K&B Ace Hardware in the city with his wife, said he would like to instill a culture of customer service.

“Our city government needs to have that same sort of culture where we’re resident-focused,” said Littmann, who served on the city council for five years before his term ended in 2017.

“So often I hear complaints that it took me so long to get a response,” he said. “That’s not good customer service.”

O’Shea said he would ensure the city conducts shared services with Anne Arundel County and the state. In addition, he would “reduce redundancy,” making cuts at the administrative level and “not in the people that do the jobs.”

Pindell Charles, who has served as alderwoman on the city council since 2009, defended and supported the current and previous administrations and city workers. She also said the city already does shared services, or partnerships, such as public safety and procurement with the county.

“We have three stellar bond ratings and I think we [should] be proud of that,” Pindell Charles said. “Nevertheless, we need more focus on our working class and on our public and subsidized housing… There’s always more to do.”

Among the written questions from the audience was whether the candidates would support legislation to install cameras in high-crime neighborhoods, and impose a financial penalty on property owners for nonworking cameras.

All three candidates support cameras in various communities, as long it can be done legally.

Pindell Charles said the financial penalty “could be something that’s definitely looked” into.

Littmann, who said he has cameras inside and outside his business, isn’t “too crazy about the idea of fining people for not putting up cameras … We have so many restrictions on businesses. Cameras are expensive. Maintaining them is expensive.”

O’Shea said property owners shouldn’t be the only ones to face a penalty.

“If you’re going to fine people because their camera isn’t working or there’s an issue whether you don’t have them up, those city cameras should also have some sort of penalty if they’re not working properly,” he said. “What’s good for the goose is good for the gander.”

Polls for the Sept. 19 primary election will be open from 7 a.m. to 8 p.m.