So far, there’s just one contender for the Key West mayor’s gavel.

Former tax collector DeeDee Henriquez has been campaigning since last year and had raised nearly $20,000 as of Feb. 27.

Henriquez had been anticipating a challenge from current city commissioner Sam Kaufman, who initially said he would run if Mayor Teri Johnston declined to run for one last term. 

When Johnston announced last month that she would not run, Kaufman told the Keys Weekly he intended to run for mayor, which would have meant resigning his commission seat this summer, given Florida’s “resign to run” law. 

Kaufman confirmed on Feb. 27 that he would not run for mayor this year and would instead remain on the commission, which will see four of its seven members replaced this year.

Henriquez spoke at a Feb. 26 candidates event hosted by Hometown and called for unity, while pledging transparency, honesty and communication in her desire to effect change in Key West. 

In addition to Johnston declining to seek reelection, commissioners Clayton Lopez, Billy Wardlow and Jimmy Weekley are term-limited out.

Commissioners Kaufman, Mary Lou Hoover and Lissette Cuervo Carey remain in place.

So far, Henriquez is the only mayoral candidate in the race, according to the Monroe County Supervisor of Elections website at

Aaron Castillo last week entered the District 6 race, running against Thaddeus Cohen for the seat currently held by Lopez. District 6 includes most of Bahama Village, parts of Duval Street and Old Town and a corridor on Angela Street toward the cemetery. 

Castillo is a “lifelong Conch, born and raised in Key West,” he said. He is the longtime funeral director and operator of Key West Mortuary, formerly known as Castillo & Thurston Mortuary on Whitehead Street.

Castillo has served on the Bahama Village Redevelopment Advisory Board, the Citizens Review Board, the Monroe County Housing Authority Board and several others. 

He spoke at the Feb. 26 Call for Candidates presented by Hometown, a nonpartisan voter education group, saying, “Bahama Village needs a lot of work, and I’m here to stay. I’m planted and I’ll work to my bones to get things done.”

Cohen is an architect by trade who worked as Key West’s planning director from 2015 to 2017. From 2004 to 2007, he was secretary of Florida’s former Department of Community Affairs, which regulated development in the state. He has additionally worked in county-level administration, planning and growth management positions throughout Florida. Cohen also was a finalist for the city manager position last year following the retirement of Patti McLauchlin.

At the Hometown event, he touted his success in securing Truman Waterfront from the navy for the city of Key West as well as his role in creating the successful Duval Loop free bus route around Duval Street. 

Although not yet registered as an official candidate, John Wilson Smith said at the Feb. 26 that he is running for the District 6 commission seat. “We need change and I’m that change. I am not an insider. I am you,” he said. 

As city races are nonpartisan, they could be decided during the Aug. 20 primary election. If one candidate for an office receives more than 50% of the vote, that candidate is declared the winner in August. In races with more than two candidates, the top two vote-getters will proceed to a run-off election on Nov. 5.

As of Feb. 27, the District 6 seat was the only race that had drawn more than one candidate.

Former Key West Police Chief Donie Lee is running for commissioner Billy Wardlow’s seat in New Town’s District 3.

Lee is a native Key Wester who served for 25 years with the police department, including 10 years as chief. Speaking at the Feb. 26 candidate event, Lee said he then opened a private security company in the Keys. He pledged to work for the local residents and “do everything in my power to make it affordable for our working families and senior citizens to continue living here.”

Meanwhile, in District 1, Monica Haskell has filed to run for the Old Town seat currently held by commissioner Jimmy Weekley. 

Haskell has held positions in Keys government since the 1990s and co-founded the first charter school in Monroe County.

“I pledge to protect the quality of life and work for the needs of our residents and businesses,” Haskell told the Hometown crowd on Feb. 26. 

Haskell, who has a master’s degree in business management, has served on the Monroe County Planning Commission, the Key West Sustainability Advisory Board, the Florida Keys Contractors Examining Board, the Key West Art in Public Places board, and the Truman Waterfront Park.

The primary election takes place Aug. 20 and the 2024 general election is Nov. 5. For information about candidates, visit

Mandy Miles
Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.