Littmann Holds Commanding Lead In Annapolis Mayoral Race

By William J. Ford, Maryland Matters

September 17, 2025

Jared Littmann began his quest more than a year ago to seek the Democratic nomination for Annapolis mayor. The local businessman hopes early tallies show his work has paid off.

In early returns Tuesday night, Littmann had 1,371 votes in the Democratic primary to 771 votes for City Council Alderwoman Rhonda Pindell Charles (D), who is seeking to become the city’s first elected Black mayor.

But Littmann said he believes mail-in ballots, which have yet to be counted, could account for as much as 30% to 50% of the final total. While she didn’t put a number on it, Pindell Charles also said Tuesday’s votes were just round one of the race.

Election officials said it may take up to a week to count the mail-in and provisional ballots and declare an official winner.

But both Democrats were upbeat as they relaxed with supporters at watch parties after the polls closed.

Besides Littmann’s family, dozens of supporters joined him at Seasalt Annapolis to celebrate, including several who sported the blue-and-white campaign T-shirts.

“We’ve had a strong volunteer group from the beginning, and they continue to show up today, both to help me at the polls and celebrate our campaign today,” Littmann, 53, said in an interview. “All that felt great … but no one will be able to claim victory today, unless you just assume that the same trajectory today will be mirrored in the mail-in ballots.”

Not far away, Pindell Charles, 71, was also hopeful as she drank bottled water and ate some chips and salsa with more than a dozen family, friends and supporters at the Pella Windows on West Street.

Jared Littmann chats with supporters at a watch party Tuesday, alongside his children. (Photo by William J. Ford/Maryland Matters)

“I feel good,” she said, before summarizing a background that includes work as a school community outreach specialist, prosecutor in Baltimore City and a brief stint as acting mayor in 2020.

“I’m ready for it [serving as mayor] because I’ve had great opportunities and experiences,” Pindell Charles said. “I’m not trying to be critical of my opponent, but he doesn’t have the depth and the breadth of what I’ve had.”

At least two voters, Christie Burt and Tory Budd, braved the rain Tuesday evening to cast their ballots at the Michael E. Busch Annapolis Library for Pindell Charles. Budd said she would like to see history made by having the city elect its first Black mayor.

“We’ll just put another white boy next to another white boy and it’s going to be another white boy battle,” Budd said of the coming general election. “She’s [Pindell Charles] got the record. She’s a lawyer. She’s capable. I’ve seen her work. She deserves it.”

Whoever receives the Democratic nomination will face Republican Bob O’Shea in the Nov. 4 general election. O’Shea ran unopposed Tuesday. The winner will replace current Mayor Gavin Buckley (D), who is term-limited from serving a third, four-year term.

City Council races

The city also had Democratic primary contests in four of the city’s eight wards. Here’s a summary of the unofficial results.

In the most-crowded race, Ward 1 Alderman Harry Huntley was leading in his reelection bid Tuesday with 256 votes, to 162 votes for Katie McDermott, 67 for Ron Gunzburger, Genevieve Torri with 10 and Ben Bramsen with nine.

The nominee will face unaffiliated candidate Thomas Kriek in November.

The Ward 3 seat is open after Pindell Charles decided to run for mayor. Keanuú Smith-Brown had 219 votes in early returns, compared to the 44 votes received by Deborah “Debbie” Odum. The winner will face unaffiliated candidate Mike Dye.

The Ward 4 race to succeed Alderwoman Sheila M. Finlayson, who did not seek reelection, was neck-and-neck, with 86 votes for Coren Makell and 84 for Janice Elaine Allsup-Johnson. The Democratic primary winner could run unopposed in the general election, because no Republican or unaffiliated voter had filed to run for that seat.

Craig Cussimanio had a lead for the Ward 6 seat with 112 votes, versus Diesha Contee who has 69 votes. The winner will face Republican George Gallagher in the race to succeed Alderman DaJuan Gay, who is not running for reelection.