Gavin Buckley, the Australian restaurateur-turned-politician, has experienced highs and lows during eight years as Annapolis mayor.
He helped the city navigate the economic downturn that accompanied the COVID-19 pandemic, remodeled a failing parking garage to bring more spaces downtown and marshaled support for the transformative City Dock project to protect against floods driven by climate change.
The mayor responded compassionately to the 2018 mass shooting that killed journalists and staff at the Capital Gazette, dealt with historic flooding events and faced persistent questions stemming from his relationship to the city’s Market House lease.
Before he was elected Buckley unsuccessfully bid on a Market House lease, and a partner in some of Buckley’s other businesses and two other people now lease it. Buckley has no financial interest in the lease and has abstained from City Council votes on the matter, but the arrangement was criticized during his tenure.
Through it all, Buckley, a Democrat who is term-limited, has brushed off criticism, maintained his enthusiasm for the city and stayed focused on the job.
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His successor, fellow Democrat Jared Littmann, will be sworn in Monday.
The Banner sat down with Buckley, 62, before Thanksgiving to discuss his time in office. The interview has been edited for clarity and length.
What do you hope people say about your eight years as mayor?
I hope people say that he did what he said he was going to do.
I told people, “If you think everything’s perfect, you know, nothing needs to change, then don’t vote for me. But, if you want someone that’s going to come and try new things and not always be right, give me a chance.”
And I think I’ve delivered on most of the things that I’ve said.
What scares you about the next four or eight years in the city?
I have trust in Jared Littmann. We always react to the loudest people. But your job as mayor is to do the most good for the most people, not just the loudest.
We’re all staring down the fact that we failed to create enough housing. So if you want more homelessness, if you want more crime, all those things that come from desperation, then don’t address that. But I think all those candidates ran on housing, so I hope that they are being true when they ran on that platform.
What do you remember as your best day in office?
Probably Inauguration Day. My mom was there; my family were there. We closed the whole block of the street where I was part of changing that street into a kind of an arts district, in front of a mural that kind of got me in trouble with historic preservation.

Note: Buckley had a mural painted on the wall of one of his restaurants without getting approval from the Historic Preservation Commission. It was retroactively approved.
It was a symbolic day, and it was my first real speech. It was pretty euphoric.
What about your worst day in office?
Obviously the Capital Gazette shooting was a terrible moment.

What lessons did you take from that mass shooting? What stuck with you?
When the shooting happened, I reached out to mayors that had recently experienced that kind of violence.
No one thinks that’s going to happen in their city. People think Annapolis is Mayberry. That showed me that this senselessness could happen in any city in America.
What do you think is the best decision you made as mayor?
Getting the right directors. You’re only as good as the people that are around you. The decision to make sure that the city was inclusive, more diverse from top to bottom. So the kids could look up and say, “Oh, I could be the parks and rec director, I could be the police chief.”
So I’m proud of that. And the City Dock project. The decision to move forward on City Dock and actually tackle it, knock down this garage, finance it in a creative way. … They’re some of the decisions I’m happy with.

What about regrets — are there any decisions you’d undo or do differently?
My staff wouldn’t agree with me on that, but, the bike lane, I would do that [again] tomorrow. I thought, “Well, let’s do a trial bike lane [on Main Street]. Wouldn’t this be fun?” And I really didn’t ask for permission, because I knew that it would be shot down.
So that’s the one that everyone would say is a bad decision.
And then the mayor’s dinghy, that’s another one where people think that’s a bad thing. But I think it’s cool that a mayor of the city of Annapolis, one of the most important maritime cities in America, comes to work in a boat.
Note: Buckley persuaded the City Council to let him dock his personal boat in places where it normally wouldn’t be allowed due to its size.
You don’t think you’d do either thing differently?
No, I wouldn’t. Australia’s all kind of half-convicts. We’re all anti-establishment. When you become part of the establishment, it’s hard to shake that. If I think people are unreasonable, I can’t control myself. I have to kind of poke them a little harder or agitate them, and that’s probably a failing on my side.
One critique you’ve faced is that you have that “move fast and break things” attitude, that you shoot from the hip with some decisions. Do you think that’s fair?
I definitely do. No question. This is a historic town, and change is a really hard thing here. So, yeah, I definitely do that.
People say I don’t listen, that I’m not transparent. I listen to everyone. I listen all the time, but what they really mean is he’s not doing what we tell him to do, and that’s at the root of it.

The other major criticism is that — like with “dinghy-gate,” or the Market House lease or even hiring your lawyer to litigate the city’s $400 million lawsuit against the opioids industry — you’ve often used the office to benefit yourself or your friends.
This is a small town. I know everybody, and I and people that I know shouldn’t be punished just because I’m running for mayor, right?
That lawyer, Joe Gormley, brought [the opioids case] to us well before anyone was thinking about this. My feeling is, it’s not fair to cut people off that you know, just because you’ve decided to be mayor. But also, when you’re in office, you do want to work with people you trust.
And I’ll defend the Market House all day long. I committed to fixing the Market House. The Market House works, pays more rent than it’s ever paid.
All those critics, they could have put a bid in for the Market House. I am connected to the Market House. I’ve never denied that. The market dictates what the city can carry, in my view, and so I’m proud of that work. And people who don’t agree are just sore losers.
Do you think the new lease agreement that the council recently approved for Market House is a good deal?
I don’t know all the details, but we do long leases. The boat shows had a long lease forever. It’s good for them to get a good deal at the Market House. Maybe we could squeeze more money out of them. But then the only people to be able to pay that money are national chains, like those guys who have massively deep pockets.
You’ve talked a lot about your accomplishments in diversity and inclusion. This month, we saw Anne Arundel County apologize for its role in slavery — but some advocates have said it’s not enough, it hasn’t been enough. Do you think you or the city should have done more on those issues?
I didn’t grow up here, so I have a different lens. I’m definitely not perfect, right? You know, we definitely haven’t talked about reparations. I mean, we’re a small city.
I think I’ll let my actions speak for themselves. I’ve worked to preserve historic African American sites, modern sites. I’ve promoted people in the communities and made the city more diverse.

What do you want to do next?
I would have had a decent shot at county executive. It’s a natural progression. I think I’ve got good support in the county, but my family comes first. Eight years of being an executive is hard on your family. My wife personalizes online attacks, so I think she needs a little bit of a break.
But I’ve built some great relationships here and I feel like Maryland is heading in a great direction, so I’m going to try to be part of branding a triangle between Annapolis, and D.C. and Baltimore, and talking about the power in that triangle, the assets in the triangle, the quality of life in that triangle.




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