Barroso Exit Talks Begin as Key West Officials Split Over What Comes Next

Last week, Key West officials voted 4-3 in favor of directing the City Attorney to begin negotiations on a possible separation agreement with City Manager Brian L. Barroso.

The move followed Commissioner Donie Lee’s proposal to explore an amicable separation that could bring Barroso’s tenure to an end.

Commissioners Aaron Castillo, Lissette Carey, and Mark Rossi opposed the resolution, while Commissioners Monica Haskell and Chris Massicotte joined Lee and newly elected Mayor Sam Kaufman to form the majority. Any final agreement must return to the City Commission for approval.

Barroso, for his part, told commissioners during the September 22 meeting that he wants to remain in the job.

Kaufman now says, however, that any deal should not close the book on questions surrounding Barroso’s tenure.

“A separation agreement would address the City Manager’s employment relationship with the City,” Kaufman told Palm and Prejudice. “It would not resolve the separate questions that have been raised about management practices, employee complaints, and other matters that deserve an independent review.”

That marks a firmer position than Kaufman took before negotiations were authorized.

As previously reported, the mayor initially said he wanted to see a concrete separation proposal before deciding whether further independent review was warranted.

Now Kaufman says plainly that he continues to support one.

That puts him at odds with Commissioner Donie Lee, who authored the successful separation resolution.

Lee previously told Palm and Prejudice that he would not support further investigations if a separation agreement were reached. He believed that money spent on prolonged investigations could instead go toward severance and avoiding potential litigation.

Lee pointed to a 2025 invoice from RC Law Group showing 34.9 hours of work on an investigation concerning former Planning Director Katie Halloran, including interviews, document review, and preparation of factual findings.

The total?

$12,215.00

“I understand the public’s desire to know,” Lee said at the time, “but I don’t think that would be a good use of taxpayers’ dollars, especially if sustained findings weren’t going to be used for cause to terminate or disciplinary actions.”

Asked after the September 22 vote what terms he would support and what he expects from negotiations, Lee said he would “reserve comment and allow the process to develop.”

Kaufman, meanwhile, earlier this month released an extensive list of concerns and allegations involving Barroso’s management of City Hall, while acknowledging that some had not yet been independently established. His statement called for an outside investigation into matters ranging from employee complaints and management practices to access to City staff and information.

The mayor now says the purpose of such an investigation would be to establish the facts, provide accountability where appropriate, and help the City identify changes that may be needed going forward.

"I believe our employees and the public deserve that independent review."

He also told Palm and Prejudice that Key West should begin preparing for the possibility of a transition.

"We should not assume the outcome of the negotiations, but responsible planning means considering how we would ensure continuity and an orderly transition if an agreement is reached."

Commissioner Mark Rossi, who opposed opening separation negotiations, told Palm and Prejudice he remains concerned about the potential cost to taxpayers. Rossi estimated a separation could ultimately cost a significant figure if attorneys become involved.

Rossi said he would prefer to see Kaufman and Barroso resolve their differences and continue working together, but acknowledged that may not be realistic.

“They’re two grown men. They should resolve their differences and move on,” Rossi said.

Asked who he believed was more likely to ultimately leave City Hall if the relationship cannot be repaired, Rossi said, “the person that's probably going to go will be Brian.”

The Commission has now authorized one process aimed at determining Barroso’s future. Kaufman is arguing for another that would examine unresolved questions about his tenure.

Whether four commissioners ultimately support both remains an unanswered question.