I was at an anniversary party for a popular Annapolis restaurant, a milestone in more than just years.

Gavin Buckley is one of the owners. Three months from the end of his second term as mayor, he drifted from table to table Sunday night, laughter following him.

Buckley and his partners recently shortened their restaurant’s name from Tsunami to just Tsu — which, in Japanese, means going from Harborwave to just Harbor. It’s an ironic touch in a city struggling with another kind of wave.

I’m not quite sure how many words I’ve spilled on City Dock. Not the $100 million that likely will be spent on protecting it from climate change-driven flooding, but lots nonetheless.

Today, the project awaits a $33 million federal grant. Work around the edges has started, but until that check arrives, the outcome remains adrift.

Burr Vogel, the city public works director, said Saturday that the Federal Emergency Management Agency has signed off on the plan, almost. The cultural resources plan is a few signatures shy.

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A 30-day review and an unexpected step — scrutiny by the U.S. Department of Homeland Security — are next.

If — or when, as the ever-confident Vogel says — the money comes through, the candidate picked by voters this fall to be the next mayor will complete City Dock’s remake, probably in 2027.

And if it doesn’t, one of the three candidates — Jared Littmann, Rhonda Pindell Charles or Bob O’Shea — will figure out what happens next.

After that, well, almost nothing.

That was the other ironic thing about the party at Tsu, a sort of crossroads of the city’s past, present and future.

Buckley and his partners were among the pioneers who caught the last tsunami of change in Annapolis, redeveloping seven dilapidated blocks of West Street into trendy shops, restaurants and homes.

Annapolis will finish the City Dock project, one way or the other.

But none of those seeking to cut the ribbon on Buckley’s legacy project has much to say about where they will go beyond steady government, better government or smaller government.

If the past 25 years is any guide, change is coming, ready or not.

This campaign season, I’m exploring problems that Annapolis’ next mayor and City Council will face when they take office in December.

Democrats go to the polls for a Sept. 16 primary, followed by a general election Nov. 4. Between now and then, voters should ask what the candidates want future Annapolis to look like.

The job has power to shape it, and not just at City Dock. At the turn of the 20th century, two mayors, Al Hopkins and Dean Johnson, focused on “inner West Street.”

They created the conditions for bringing new life to the seven-block stretch of dated commercial buildings best known for petty drug dealing and strolling prostitutes.

Successive mayors, a Democrat and an independent, built the Knighton Garage and Westgate Circle. Their administrations coordinated state incentives for development and new business.

West Street (few call it “inner” anymore) fulfilled the vision. It’s a walkable place to eat and shop, with office buildings and townhomes mixed in among the graceful surrounding neighborhoods.

It’s not perfect. Office vacancy rates are higher than they should be. There’s still a big empty lot, and homes remain too expensive for most young people. Pockets of poverty and crime are right around the corner.

But more homes are coming, and well, everything is close to everything in seven-square-mile Annapolis.

What happened there is materializing farther out, along the 1.3 miles of outer West Street from the Michael E. Busch Annapolis Library to the city line — “Upper West Street,” as Charles prefers to call it.

It’s home to car dealerships, fast food drive-thrus and faded strip malls. Pioneers already see the potential.

Bell Annapolis came first, opening in 2000 as condos and then changing to apartments. Classic Theatre of Maryland renovated an old Pepsi bottling plant for its home, and Black Market Bakery is about to move in next door.

Two Navy grads busy converting old downtown buildings into boutique hotels created 1313 West on the site of a former bed and breakfast. The Chesapeake Conservancy just opened the Earl Conservation Center, something they hope will be a hub for environmental groups.

The city moved its public works headquarters to the area and partnered with a developer of affordable housing to build 42 townhouses nearby.

Across the city-county line, even more change is building. More than 1,500 homes are coming, new retail shops have opened and Annapolis Mall has new owners.

Charles is interested in the redevelopment of public housing. But after City Dock is made over, the next mayor won’t have any choice.

West Street is evolving, and the question is whether anyone will lead it.

Charles and Littmann, the Democratic mayoral candidates, favor following the City Dock plan set in motion by Buckley.

It would raise a green space 8 feet above the water, add pavilions and a splash park, pop-up flood walls and pumps. A maritime center would follow, attached to a historic waterman’s home.

Developer Harvey Blonder wants to lean into these changes, replacing his existing restaurant on Dock Street with a waterfront hotel. His plan requires easing height restrictions, a major test for the outgoing City Council.

Without the $33 million federal grant, City Dock could go back to the design stage, adding at least two years to the timeline.

Littmann would save what he could and move forward. The splash park might be dropped, along with elements of the maritime center.

O’Shea wants to pause and review the financing and the design.

The City Dock remake seems likely to spawn more change, and the next mayor will cut ribbons on other long-germinating Buckley projects.

None may be more symbolic than WEE, The West East Express Trail connecting downtown with Waterworks Park, west of the mall.

It will parallel West Street, traveling from the past and present into the future of Annapolis.