Mayors of Annapolis tend to fade quickly from public view.

Everyone is tired after four or eight years. Sometimes they go gracefully, sometimes still striving for attention.

Then there’s Gavin Buckley.

Six months after leaving the mayor’s office, the brassy restaurateur is on the ballot again this month. He’s one of five candidates running in the Democratic primary to represent District 6 on the Anne Arundel County Council.

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For some, it’s a referendum on his two terms.

“Half the ticket that I’m running against wants to drain the swamp, I think,” he said.

Buckley, if you missed the point, is the swamp in that metaphor.

“It’s funny, because eight years ago, I was the outsider.”

Call it people who are tired of him. Call it the anybody-but-Buckley crowd. Whatever you call it, he’s defending himself from the haters just fine.

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“I’m the target,” Buckley said. “The loudest people have really controlled the narrative here for a long, long time. And when they say you’re not transparent or you weren’t listening, generally, they mean ‘You didn’t do what we told you to do.’”

So, some former allies don’t return his phone calls. Some are lined up with a coalition of candidates, the Anne Arundel Democracy Slate, topped by Councilwoman Allison Pickard who’s running for county executive.

Community and environmental activist Joe Toolan isn’t on the slate, but he is campaigning for the District 6 seat with Pickard and members such as Del. Dana Jones. School board member Joanna Tobin endorsed him, and so has House Speaker Joseline Peña-Melnyk.

Sit with Toolan, and it becomes clear that he’s a deeply knowledgeable candidate who’s spent months listening to what people want. He’s knocked on the doors of 4,000 Democratic voters, and regrets that he won’t get to the remaining 6,000 before polls close Tuesday.

Yet even he sees how views of Buckley have shaped the conversation.

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“It’s interesting, right?” Toolan said. “I mean, I think that because Gavin was the mayor for eight years, there are people who are very critical about how he led the city.”

Toolan isn’t always one of them. He worked well with Buckley, he said, but disagrees on some of his record.

Joe Toolan, a longtime community activist, is a Democratic candidate for County Council in District 6.
Joe Toolan, a longtime community activist, is a Democratic candidate for County Council in District 6. The bird on his sign is a quetzal, the national bird of Guatemala, the country where he was born. (Rick Hutzell/The Banner)

Buckley has fans. He’s one of just two candidates countywide who opted for public financing. He’s collected hundreds of donations ranging from $5 to $250, outraising the others by better than 4-to-1.

County executive candidate James Kitchin, the only other one relying on public financing, endorsed him. So did Gov. Wes Moore, County Executive Steuart Pittman, outgoing Councilwoman Lisa Rodvien and her predecessor, Chris Trumbauer, now the county budget director.

There are issues beyond the former mayor’s record. There is tension between the need to build homes people can afford and fears of overdevelopment.

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Another candidate, however, predicts that as Baby Boomers die, their homes will fill most of the need.

“There’s a silver tsunami of housing inventory that’s going to start coming on the market in 2030 and it’s expected to last, the next, you know, 15 years,” Katie McDermott said. “We have the opportunity if we’re smart and can manage it.”

The next council member will have a say in where development should go, whether to loosen rules controlling it and to regulate developers’ dollars in political campaigns.

Housing is intertwined with traffic and the environment. Budget votes can make the council member an advocate for Annapolis schools.

There’s immigration. Buckley, Toolan and fellow Democrat Dominik Prokop are all immigrants. Buckley was in the country without a visa in his youth.

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Only Toolan, born in Guatemala, has seen people who look like him rounded up by a federal government that casts immigrants as a threat.

If Buckley has his haters, then Toolan has confronted hate, too.

A former president of Annapolis Pride, he would be the council’s first openly gay member. He’s an immigrant. He sometimes sports a nose ring.

There have been trolls, bigots and scary moments. He’s had to call the police.

“We see people who want to push back against people for being who they are, right?” he said.

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Other issues are less frightening — a water tower in Heritage Harbor and access to publicly owned land on Valentine Creek.

Toolan says the solution is the same.

“The reality is, even if we don’t agree with people, we should try to take time to meet with them,” Toolan said.

Nobody in the 6th District primary has focused more on Buckley’s record than McDermott.

Katie McDermott, a Democratic candidate for City Council in Ward 1, was still posting campaign signs outside polling places in the Annapolis primary on the morning of Sept. 16, 2025.
Katie McDermott ran for the Annapolis City Council and rolled out signs with the same design and color scheme for her current County Council bid. (Rick Hutzell/The Banner)

She’s criticized him on the renovations at City Dock, on regulating short-term rentals and over public housing inspections that ended twice in multimillion-dollar lawsuit settlements.

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McDermott talks about her ideas, too, such as support for creating a county inspector general and being an advocate for neighborhoods.

But criticism of the former Annapolis mayor has been part of her campaign.

“I think when you have a record, it’s appropriate to discuss,” McDermott said. “He brings a lot to the table at the end of the day, though.”

Early voting ended Thursday.

Democrats embrace it and mail-in ballots, so this election might already have been decided. Or maybe it’s so close it will be a week before a winner is clear.

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If it’s Buckley, he would be the first Annapolis mayor since the 1950s elected to anything after leaving office. Some of what might follow could seem familiar.

On bright yellow campaign signs rolled out in the final weeks of the campaign, Buckley rides a bicycle over the tagline — “Powered by people. (And often his bike.)”

He made bicycling central to his terms as mayor, starting bike lane projects and projecting a two-wheeled culture for Annapolis. He wants to do the same outside the city.

Six months after he left office as mayor of Annapolis, Gavin Buckley is running for Anne Arundel County Council.
Six months after he left office as mayor of Annapolis, Gavin Buckley is running for Anne Arundel County Council. (Rick Hutzell/The Banner)

The winner of Tuesday’s Democratic primary will most likely be the next councilman. It’s just numbers. If it’s Buckley, that’ll drive the anyone-but-Gavin crowd nuts.

He’ll probably enjoy that.

“I still see myself as an outsider, because there’s an establishment thing happening now with that democracy slate,” Buckley said. “Or whatever it is.”