Jared Littmann and I talked about his run for mayor of Annapolis.
This was in December 2024, 11 months after the lawyer-turned-hardware store owner launched his campaign, and 11 months before it concludes on Tuesday when polls close.
We talked about his central pitch, a plan to make the city run better.
No grand vision. No radical changes. Just get the job done, better than it’s been done before.
Competence as a winning strategy.
“People are looking for a more responsive city government,” he said. “I hear over and over again complaints of ‘I sent in this, this issue, this email, this call, and it took four months to get a response, and then they responded with something that I told them.’
“I plan to have a customer-focused approach to city government, a culture of getting to yes. It doesn’t necessarily mean any crazy, every idea gets approved, because we’re obviously gonna have rules, and everyone’s gonna live by the rules.”
Less than 48 hours from Election Day, Littmann’s campaign has an air of inevitability. He sucked up so many endorsements, donations and volunteers that he chased off all but one Democratic rival.
“I was mad at Jared getting in so early,” former alderwoman Elly Tierney said in August 2024 after announcing her retirement. “There should be a law against that. Really. I was just angry.”
He trounced the sweet, quirky campaign of his primary challenger, Alderwoman Rhonda Pindell Charles.
And, unless something wholly unpredictable happens, Littmann is about to do the same to his Republican opponent, Bobby O’Shea.
The Democrat is so confident, his campaign announced a 100-day plan one week before Election Day — tantamount to declaring victory before the polls open.
“I’m putting in the work now to be fully prepared for Inauguration Day on Dec. 1,” he said in the campaign email. “To run a great city, you have to get your own house in order first, and that’s exactly where I’ll start.”
There’s always a risk of being overconfident, of being so self-assured that you stake a claim to the office of mayor two years before the current occupant moves out — only to stumble.
But the result this time is an election that feels like a foregone conclusion, and has for months. How did Annapolis get here?
Part of the problem lies with the Republican Party in Annapolis.
O’Shea, who ran unsuccessfully for mayor eight years ago, has the insurmountable disadvantage of running for the perpetual society of also-rans in the deep-blue capital of a deep-blue state.
Worse, he’s campaigned on ideas that every city Republican has tried over the last 20 years: cut taxes and services before Annapolis runs into a financial ditch.
“As I see and understand the budget, the city’s in good financial shape,” Littman told me in December. “It’s in great financial shape.”
It’s not just O’Shea. Republicans only fielded candidates in four of eight wards, and Democrats are painting the independents in three other wards as Republicans in sheep’s clothing.
When I talked with Littmann again after his first one-on-one forum with O’Shea, he seemed confused by his opponent’s reliance on the universal Republican playbook — despite facts that show doom isn’t looming.
Bonding agencies, which finance debt as an investment, paint the financial outlook as rosy. The rates released in the final weeks of October held stable, Aa1 from Moody’s and AA+ from S&P and Fitch Ratings.
All three praise Mayor Gavin Buckley and the City Council for addressing the city’s pension debt. Analysts laud Annapolis’ solid property tax base, robust economy and strong financial reserves. They credit Buckley’s adoption of modern accounting and budgeting practices.
Every election is a response to the results of the last one. This year is no different.
Where Buckley ran in 2017 as a visionary, Littmann talks about improving the process.
The outgoing mayor has kept his head down during this campaign, suffering the role of everyone’s political piñata. He’s been a good sport, throwing Littmann a fundraiser last week and linking him to the success of the massive City Dock project during the latest downtown flooding.
That was just days after Gov. Wes Moore kicked off a door-knocking campaign for Democrats, with the mayor’s race as the top objective.
Compare that to O’Shea’s final fundraiser, where former Gov. Bob Ehrlich talked up his latest book on the greatness of President Donald Trump.
If you look at Littmann’s 100-day to-do list, there are no radical changes. He’ll meet with the staff, communicate with residents and bring in some new faces. He’ll have three months to create and submit a budget.
Planning and Zoning Director Chris Jakubiak, police Chief Ed Jackson and Recreation and Parks Director Roslyn Johnson seem most likely to get a hard look from the new mayor.
There’s no surprise, either, in his key projects — improving permitting, addressing complaints about parking, working on public safety, adopting more controls on short-term home rentals and finishing City Dock.
That makes Burr Vogel, who oversees the project as public works director, the department head most likely to stay.
Just to drive home what’s at stake on Tuesday, Buckley will hold a groundbreaking ceremony Monday on the $100 million flood protection and park plan he’s handing off — even as it awaits final federal funding.
There is a danger of being wrong in predicting an election.
O’Shea has been a happy campaigner, talking emphatically about taxes, traffic, public safety and pausing the City Dock project.
An uncontested election is worse than one without suspense, and Annapolis can thank O’Shea for that.
But consider this. On primary night, Littmann delivered a victory speech at his watch party.
He never used that word before the affluent, mostly white crowd out of respect for his opponent.
In a private aside, though, he shared his polling and poll-watching results. They accurately forecast both the outcome and the margin.
Similar insights undoubtedly led him to release his 100-day plan.
It’s a modest declaration of inevitable victory, offered once again before the counting‘s done.
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