The starting signal in Annapolis has long since been fired

On a beautiful late summer evening on a patio overlooking an undeveloped stretch of Spa Creek in Annapolis, it was hard not to think about the natural surroundings. And that’s what about two dozen environmentalists and neighbors gathered to discuss with a local business owner named Jared Littmann, who is running for mayor.

“This is the perfect place for a meeting of environmentally conscious people,” said Annapolis Alderman Rob Savidge (D), a Littmann supporter, as a dragon boat carrying 22 rowers glided past.

More than 13 months before the local elections in Maryland’s capital, this kind of gathering has become commonplace for Littmann. Littmann, a former city councilman, declared his candidacy for mayor in January, an unusually early start.

For months he had the field to himself. But that has simply changed.

Councilwoman Rhonda Pindell Charles (D), who has served on the city council since 2009, formally announced her intention to run for the seat held by outgoing Mayor Gavin Buckley (D) on Monday evening in an impressive display of political strength – a rally that drew more as 250 supporters to St. Philip’s Episcopal Church on Bestgate Road.

Littmann and his team welcome the competition.

“It’s hard to run against yourself,” said Laura Richards, an Annapolis business consultant and former restaurateur who is Littmann’s deputy campaign manager.

Littmann said he expected a large field from the start. The last time there was no incumbent in an Annapolis mayoral election in 2009, a dozen candidates ran. Annapolis is one of three Maryland communities — Baltimore and Frederick are the others — that hold partisan elections. The Democratic primary does not take place until September 16, 2025, and the candidate filing period is next July.

“If Kamala Harris can run for president in 100 days, someone can run for mayor of Annapolis in 30 days,” Littmann said.

Still, starting so early gives Littmann undeniable advantages, and he is campaigning full-time.

“Before I had to ask people to volunteer, I knew I had to address the issues and I knew I had to raise money,” he said. “I have such a busy campaign schedule every day.”

As of June 30, Littmann had raised $104,000, a significant sum for a campaign in a city of 41,000. He expected it would be harder to raise money later in the year as voters’ focus turned to school board and federal elections.

“I’m glad I’m not in the position of having to beg for money now,” he said. “We’ll start again in 2025.”

Littmann was able to receive some key initial endorsements from Anne Arundel County Executive Steuart Pittman (D), former Mayor Ellen Moyer (D) and a number of current and former local elected officials.

“I saw Jared as a city councilman, Jared as a businessman, Jared as a father and husband, Jared as a member of the Annapolis and Anne Arundel Resilience Authority and Jared as a candidate for mayor,” Pittman said. “In all cases he listens, he hears and he acts.”

Most importantly, from Littmann’s perspective, the early start has allowed him to engage with local issues and meet with community leaders to help him develop a campaign platform. Littmann tried to avoid the endless series of coffee drinking sessions that often characterize a young candidate’s first days on the campaign trail. Instead, he tried meeting people for walks in local parks.

“I’ve never seen a more organized campaign for local office like this,” said Bob Gallagher, a retired lawyer and environmentalist who hosted the meeting for Littmann at his home the other night.

Gallagher said he has been trying to get Littmann to run for mayor for about a dozen years. After serving on the City Council for five years and ending his term in 2013, Littmann had long thought about running for mayor. But he wanted to wait until his children, now sophomores in college and high school, got older. He also wanted to focus on running K&B True Value, a hardware store on Forest Drive in Annapolis that has been owned by his wife’s family for half a century.

“He said yes [to running for mayor]”But in his always thoughtful way, he said he had some goals for his business and for his family, and let’s stay in touch,” recalled Gallagher.

Littmann also served on the national board of True Value Hardware for several years, which he describes as a tremendous learning experience that gave the private sector valuable insight into budgeting and best management practices for the chain’s 4,500 stores. He has vowed to govern with “a customer-centric approach” if elected.

But that’s just part of Littmann’s resume. He earned a bachelor’s degree in environmental engineering and then earned a law degree. He spent time as an assistant district attorney in Montgomery County. During his five years on the City Council, Littmann focused on tax and environmental issues, including promoting a forest conservation law that has become a model for state and local politicians throughout Maryland.

“I learned from Jared what it meant to be a city councilman,” said Savidge, who succeeded Littmann on the city council. “He got a bird’s eye view of what it takes to make a good mayor. He’s so focused on process and good government…He has a reputation for being respected because he cares.”

A unique figure in Maryland politics, a former sailor and restaurant owner from Australia, Buckley was a consequential mayor, a barrage of innovative ideas but without the ability to always put them into action. Littmann says that if he were to succeed Buckley, he would see part of his role as ensuring that the outgoing mayor’s vision is realized, with an emphasis on efficiency and community contribution.

But Pindell Charles also preaches continuity. In her announcement speech Monday, she pledged to retain all of Buckley’s senior managers.

Pindell Charles is a retired prosecutor and former state official who was praised Monday night by 10 different speakers from different walks of her life as an energetic and responsive representative of her district, but who has contacts at all levels of government to serve the entire city. She is running to become the first elected black mayor in Annapolis – Alderman John Thomas Chambers Jr. (R) served temporarily for two months in 1981 after the suicide of Mayor Gustav Akerland (R).