If Barroso Leaves, Do the Questions Leave Too?

The latest twist from a City Hall under scrutiny comes in the form of a deal that could help end the ongoing fight between Key West officials and its top civil servant. But ending the employment dispute may not answer the questions that started it.

As reported by Keys Weekly, Commissioner "Donie" Lee made a somewhat surprising revelation in the form of a proposed resolution intended for the city's September, 22, budget meeting.

Lee is now proposing that the city negotiate an amicable separation agreement with City Manager Brian Barroso that could end Barroso's employment on mutually agreeable terms.

Newly elected Mayor Sam Kaufman, who previously served 10 years as a city commissioner, has had a tumultuous relationship with Barroso, most recently escalating with his public call for an independent investigation into the City Manager’s tenure.

In a written statement provided to the press barely weeks into his tenure as mayor, Kaufman cited a series of concerns and allegations, including restrictions on his access to City Hall staff and information, what he described as the mischaracterization of a cybersecurity breach, and a contentious September, 1 encounter that Kaufman said resulted in Barroso telling him, “If you have the four votes, then terminate me.”

Kaufman, for his part, wants to see what is actually proposed before determining his next steps. He does not currently appear positioned, however, to treat any separation agreement as an automatic substitute for further review of Barroso’s tenure.

"A separation agreement and the question of whether certain matters should be reviewed are not necessarily the same thing," he said.

"My focus is on resolving this responsibly, protecting the interests of the City, and making sure any matters that warrant further attention are appropriately addressed."

Asked what would determine whether further review was necessary, Kaufman said he did not want to get ahead of the process. He plans to evaluate any proposal as a whole before deciding whether additional independent review or public discussion is warranted.

In other words, a departure by Barroso may not necessarily signal the end of scrutiny surrounding his time at City Hall.

Barroso did not respond to questions asking whether, in the event the Commission authorizes negotiations, he would be willing to pursue an amicable separation or whether he believes unresolved allegations concerning his tenure should still be independently reviewed.

Lee, meanwhile, previously voted against the September, 3 effort to preserve the Commission’s ability to revisit or terminate Barroso’s agreement.

Asked what had happened since then to prompt his proposed negotiated separation, the District III commissioner said nothing had changed other than his desire to offer another option for resolving what he described as apparently irreconcilable differences between the mayor and City Manager.

Crucially, Lee said he would not support further investigations into the unresolved allegations surrounding Barroso if a separation agreement is reached.

Lee pointed to the cost of “long protracted investigations,” money he believes would be better spent on a potential severance package that could bring “finality to the dispute” and avoid costly litigation.

“I understand the public’s desire to know,” Lee said, “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.”

“Ultimately, we have to make business decisions that aren’t always perfect.”

Lee said his concerns about investigative costs are both general and informed by the city’s past experience. He provided Palm and Prejudice with 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.

That invoice does not estimate what an investigation into the matters raised by Kaufman would cost. It does, however, offer a recent example of how even a single outside investigation can quickly run into five figures.

Lee said he will wait to see if the resolution passes before setting limits or beginning negotiations

That leaves the Commission with two potential questions: whether Barroso should continue working for Key West, and whether the disputes and allegations surrounding his tenure should still be examined if he does not.

Kaufman has stopped short of saying a separation agreement should end further scrutiny. Lee has now said that, if a deal is reached, he believes it should.

A separation agreement could ultimately determine whether Brian Barroso remains at City Hall. What it may not determine is who was right about what happened while he was there.

No matter the outcome of the next meeting, islanders are unlikely to have seen the last of this episode.