The lawsuit bore a familiar name.

No, it wasn’t the John Doe plaintiff who claims Annapolis broke its own rules by approving plans for a $100 million resilience project at City Dock.

It was C. Edward Hartman III. The Annapolis attorney who filed the challenge for an anonymous client. It’s his latest foray into fighting government decision making.

“There are times when the government might step beyond its rightful boundaries, infringing on the rights of individuals and businesses,” Harman’s law firm states on its website. “This kind of government overreach can take many forms, from unjust regulations to inappropriate enforcement of laws.”

But this legal challenge, filed last month and yet to get a hearing date, mirrors one a decade ago over the exact same space, with many of the same ideas and even the same family of lawyers.

Ed No. 3 is named after his late father, C. Edward Hartman II. Ed. No. 2 was the Harvard-trained son of a Harvard-trained lawyer.

He opened a law firm in 1965 and played a pivotal role in winning early preservation fights for Historic Annapolis. He and his partner helped create Anne Arundel County charter government.

He was more than a lawyer, though. He founded Chesapeake Marine Tours, which operates a fleet of water taxis and charter boats today as Watermark Tours. For years, his recorded voice narrated the company’s Annapolis waterfront tours. He was an early investor and the eventual owner of the Annapolis Boat Shows.

Those two businesses, no longer controlled by the Hartman family, are rooted in the future of City Dock.

Ed No. 2 was so invested that he created and largely funded Save Annapolis. The organization worked with Historic Annapolis, the Ward One Residents Association and downtown merchants to block a novel-thinking mayor’s ideas for change at the harbor’s edge.

Josh Cohen wanted to add green space and economic growth in an area little changed for decades. The centerpiece was a waterfront boating supply store, vacant for six years. A group of investors wanted to replace it with a restaurant and entertainment center.

The building was located on Compromise Street, but no middle ground was found in Annapolis. Hartman won by delaying the project long enough that investors walked away.

Cohen lost his bid for a second term, and the plan died under his successor, Mike Pantelides.

Then, in 2017, voters replaced Pantelides with another novel-thinking mayor, Gavin Buckley. Like Cohen, he staked his legacy on City Dock.

With a plan germinated in the ash of Cohen’s failure, Buckley proposed remaking City Dock by moving 150 parking spaces off the waterfront, creating an elevated park as a flood barrier, and adding pop-up walls and pumps to keep streets and buildings dry.

“What the lawsuit will bring is costly delays, degradation of historic structures, and, inevitably, more downtown flooding,” Buckley said in a statement on the legal challenge.

It is a generational change intended to protect the city’s 350-year-old historic district from increasing floods driven by climate change. Economic change, including a public waterfront welcome center and possible new waterfront hotel, are add-ons with fierce critics.

Unlike Cohen, the plan promoted by Buckley’s administration got approved. Term-limited, he can’t run for re-election in 2025. But if Hartman’s goal is to outlast the mayor, it might be as effective as a win in court.

Annapolis mortgaged its downtown garage and street parking to raise about a third of the project cost. More money came from various state and federal sources. Another $33 million is on hold until FEMA finishes its detailed review of the project under the National Environmental Protection Act.

The project is behind schedule and might not begin until the late next year. Regional FEMA staff met with city officials last month, but if the start date goes beyond the election, a new mayor and City Council could decide they want changes.

Ed No. 3, who declined to talk to me, is not as influential a lawyer as his father. But he’s tried to be.

When Ed No. 2′s firm broke up in 1984, he and partner Bennett Crain opened another firm and brought on Ed. No. 3. He spent his early years on typical Annapolis legal business, a mix of corporate law and property disputes, maritime lawsuits and real estate settlements.

After his father largely retired in 2000, Ed No. 3 reorganized with attorney Matthew Egeli to create Hartman and Egeli. The year Buckley was elected, Egeli moved to Virginia, and the younger Hartman became the head of his new firm, Hartman Attorneys at Law.

When COVID arrived in 2020, Hartman moved into what he considers the government overreach practice.

He successfully challenged mask and social distancing rules for businesses in several Maryland counties. He sued Calvert County schools for parents who claimed an anti-discrimination policy violated their free speech rights.

He crossed paths with another lawyer, Del. Dan Cox. When the Trump-style Republican captured his party’s nomination for governor in 2022, Cox set up his headquarters near Hartman’s office.

With all signs pointing to a monumental loss to Democrat Wes Moore, Cox turned to Hartman to challenge counting mail-in ballots early to avoid a logjam after Election Day. They lost. This year, he sued on behalf of groups claiming voter registration violations and voting machine errors, which also lost.

He did win a temporary restraining order striking down Anne Arundel County’s COVID rules, which the county later withdrew, attributing its decision, however, to declining cases.

As he challenges Annapolis again, this time on City Dock, Hartman has beaten City Attorney D. Michael Lyles before.

In a fight over public water access, Hartman represented neighbors who fought the city’s claim to a small strip of land far upstream on Spa Creek.

Hartman, representing the neighbors, lost in trial court but won on appeal — a panel of judges ruled the public only had standing to sue if they could show financial damage.

In his latest lawsuit, the identity of John Doe will eventually be revealed. The city denies Hartman’s claim that it agreed to keep his identity secret.

Maybe the city should argue that Doe, whoever he is, has to show the approval process hurt his pocketbook.

Maybe it should borrow a winning idea from this son-of-a-son of a lawyer.

Clarification and correction: This story has been updated to clarify that The Banner does not know the identity of C. Edward Hartman III’s anonymous client, and that Hartman won a temporary restraining order in the Anne Arundel COVID case. It’s also been updated to correct that Hartman succeeded in some legal challenges to mask and social distancing rules during the coronavirus pandemic.