Key West city manager says he’s staying on the job

a large white building with palm trees in front of it

An amicable separation agreement requires a willingness to separate, but that’s not the case at Key West’s city hall, where the city manager plans to stay in his current position.

The city commission last month passed a resolution directing the city attorney to negotiate an amicable separation agreement with city manager Brian L. Barroso. Commissioner Donie Lee had proposed the negotiated split, which was approved with a 4-3 vote at the Oct. 1 commission meeting.

Mayor Sam Kaufman and commissioners Lee, Chris Massicotte and Monica Haskell voted in favor of the negotiations. Commissioners Mark Rossi, Lissette Carey and Aaron Castillo were opposed.

Lee’s resolution acknowledged ongoing conflicts between Kaufman and Barroso, stating, “disputes and disagreements have arisen between the mayor and the city manager; and the continuation of such disputes is disruptive to the effective functioning of city government, creates uncertainty for city employees and undermines public confidence in the operation of the city. The city commission finds that it is in the best interest of the commission, city employees and the community at large for the city and the city manager to part ways on mutually agreeable terms ….”

As it turns out, there was nothing to negotiate as Barroso “does not wish to leave his job,” city attorney Mayanne Downs told the commission in an Oct. 9 email. “The city manager has told me formally today that he wants to stay. He has met with leaders inside and outside city government. He is committed to continuing his work at the city, improving his relationship with the mayor, and he does not wish to leave his job.

“An amicable separation takes two willing parties,” Downs wrote. “I cannot negotiate one when one side does not want to separate.”

Commissioner Rossi had encouraged an improved relationship between Barroso and Kaufman at the Oct. 1 meeting.

“I really think you two guys (Kaufman and Barroso) need to bury the hatchet and get some good things done,” Rossi said on Oct. 1, before voting against the negotiated separation. “I won’t vote to get rid of Brian because it’s gonna cost the city hundreds of thousands of dollars. Is Brian rough? Yes. Is he emotional? Yes. You’re two grown men. Let’s work this out.”

It seems Rossi will get what he requested, at least for now.

“I remain committed to a professional and respectful working relationship with the city manager,” Mayor Kaufman told the Keys Weekly this week, “My focus is serving the people of Key West by promoting open communication, transparency, accountability and moving our city forward. Any outstanding matters should be addressed fairly and through the appropriate processes.”

In her email to the commission, Downs also wrote, “The city manager is the city’s chief executive, and his position is central to how Key West’s government works. The mayor believes the city should have a different city manager. But the decision is not the mayor’s alone. Under the city manager’s contract and the city charter, the city manager serves at the pleasure of a majority of the commission.

“On a personal note,” Downs wrote, “I was inspired by the mayor’s comments at his swearing-in ceremony, particularly his reference to divisions within our community, and that he did ‘not want that division to define us.’ I have also been impressed by the city manager’s statements that he is committed to improvement for the benefit of this city. I am hopeful that both can work together for the benefit of Key West.”

District IV voters to elect commissioner Nov. 3

While nearly all city and county races were decided in the Aug. 18 primary election, Key West voters — all voters — still have a few decisions to make in the Nov. 3 general election.

Voters in District 4 will choose their city commissioner in the runoff between Sarah Compton and Wayhe Garcia, the top two vote getters in the three-way race that also had included Juan Llera. As no candidate received more than 50% of the vote in August, Compton and Garcia head to a November runoff. 

Compton’s campaign, which launched several months before Garcia entered the race, has raised $75,364, according to the latest financial filings submitted this week. Garcia has raised $13,744. 

A total of 1,470 votes were cast in the District IV race during the August primary. Compton got 625 votes, or 43%, compared to Garcia’s 495, or 34%, and Llera’s 350 votes, or 24%.

How long should mayors serve?

Should the Key West mayor’s term be increased from two years to four, which would match that of their commissioner colleagues? And should the mayor be allowed to serve a maximum of 12 years rather than the current eight-year limit?

Both questions are on the Nov. 3 ballot for all Key West voters to answer. And if approved by a majority of voters, neither change would take effect until 2028.

Former mayor Dee Dee Henriquez initially proposed four-year terms for mayor in March 2025, saying, “Two years is not enough time as mayor to get things done.” 

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.

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