KEY WEST, Fla. — Key West commissioners are scheduled Tuesday to consider authorizing negotiations for City Manager Brian Barroso’s departure from City Hall, less than three weeks after a commission majority rejected an effort to preserve the city’s right to modify or terminate his contract before it automatically renews for another two years.
Vice Mayor Donie Lee is sponsoring a resolution directing part-time contract City Attorney Mayanne Downs to negotiate an “amicable separation agreement” with Barroso on a time-sensitive basis and report back to commissioners on the progress of those negotiations Oct. 1 — the next city commission meeting.
The resolution also authorizes Barroso to negotiate directly with Downs. It does not establish a departure date or set a maximum amount for severance, accrued leave, benefits or other financial consideration that could be included in a proposed agreement.
Vice Mayor Donie Lee discussed the resolution Monday morning on “Morning Magazine” with US 1 Radio’s Joe Moore.
“I’m bringing a resolution forward at tomorrow’s meeting that asks my fellow commissioners to consider authorizing the city attorney to engage in an amicable separation agreement with the city manager,” Lee said.
Lee also said commissioners’ rejection of a motion to invoke a notice provision in Barroso’s contract allowed the agreement to renew automatically.
“I think that regardless of how you want to get rid of a city manager, it costs money,” Lee said. “So I’m hoping that this, this, if we could come to an amicable separation, I’m hoping that this will potentially not cost us as much money.”
Lee said firing Barroso for cause was the only option under the contract that would avoid severance payments. Even then, he said, the city could face legal expenses.
“But it doesn’t end there. Even if you fire the city manager with cause, and he may not get severance, then what happens is when you fire with cause, usually that person will end up suing the city for wrongful termination, and that costs a whole lot of money trying to defend,” Lee said. “And just imagine if that person wins and comes back, so they not only do they come back, then you got to pay them back pay, then you have to pay them damages.”
His concerns about legal expenses come as the city faces several high-profile lawsuits, including one brought by the American Civil Liberties Union and a negligence suit involving the city’s Community Services Department, Burke Construction and RS3 Sports over turf work at city-owned facilities.
“It sounds like an easy proposition, but it’s not. So I’m hoping that there’s a way that we could come to some amicable separation agreement,” Lee said. “And yes, that it will cost money. It’s going to cost money regardless.”
Newly-elected District V representative told Above the Fold that he liked Lee’s resolution.
“I applaud Vice Mayor Lee’s efforts to finding a resolution to this. The resolution states that we are directing the city attorney to negotiate a separation on behalf of the city and I support that,” said Massicotte.
Lee also explained why he was proposing a separation agreement after joining three other commissioners in rejecting the notice motion, allowing Barroso’s contract to renew automatically with a pay raise.
“It appears to me that it that this has turned into just the difference of just irreconcilable, and I think that it’s reached a point to where it’s become a distraction to not only the commission but to to the employees, city hall, and the public at large,” Lee told Moore. “And I just think we need to bring this to to finality.”
The resolution follows a Sept. 3 special commission meeting called by Mayor Sam Kaufman to invoke a provision in Barroso’s employment agreement requiring at least 120 days’ written notice if either side intended to modify or terminate the agreement before its existing term ended.
The Right to Review, Modify or Terminate — Denied
The proposal would not have fired Barroso. It would have formally notified him that the city was preserving its contractual right to revisit, modify or terminate the agreement before it automatically renewed.
Kaufman and Commissioners Monica Haskell and Chris Massicotte voted to provide the notice. Lee and Commissioners Aaron Castillo, Lissette Carey and Mark Rossi voted against it, defeating the proposal 4-3. Sources close to the commission say that the four votes were swayed by what many believe was a faulty opinion rendered by Downs that was in contravention of an earlier appellate court ruling having to do with the same sort of provision.
Barroso’s existing term ends Jan. 7, 2027. His agreement provides that it automatically renews for another two years unless either the city or Barroso gives written notice at least 120 days before expiration of an intent to modify or terminate the agreement.
That deadline was Sept. 9.
Because the commission declined to give notice, Barroso’s agreement is now set to renew through January 2029. His current base salary is $265,000. The renewal includes a 5% increase, or $13,250, bringing his base salary to $278,250.
Lee’s latest proposal therefore would begin separation talks after the contractual notice period expired and after Barroso gained the benefit of the automatic two-year renewal.
The Unknown
The financial terms of any separation agreement remain unknown.
Barroso’s current agreement provides 15 weeks of severance if he is terminated without cause. The city may terminate him for cause by majority vote under provisions defining cause to include substantial violations of city policies and procedures or violations of ordinance or law.
Lee’s resolution does not limit Downs to the 15 weeks of severance in Barroso’s contract. It authorizes negotiations that could include a departure date, transition terms, severance, accrued leave, benefits and other provisions, with any agreement ultimately returning to the commission.
The city previously negotiated Barroso’s compensation in February. Commissioners approved a $265,000 salary, retained the two-year term and automatic two-year extension provision, kept his $500 monthly transportation allowance and preserved 15 weeks of severance.
Lee, Carey, Castillo, Haskell and then-Commissioner Greg Veliz supported the amended agreement. Kaufman and then-Mayor Dee Dee Henriquez voted against it.
Let’s Talk About Repetition… Again
There already has been one attempt to reach a negotiated separation.
Following the Sept. 3 vote, Kaufman approached Barroso through Downs about a possible agreement. Kaufman later disclosed those discussions during his Sept. 9 inaugural mayoral press conference. No agreement was reached.
Kaufman also has called for an independent investigation into Barroso, citing concerns involving workplace conduct, intimidation, representations made to commissioners and potential interference with elected officials. Some involve documented events; others remain allegations or unanswered questions. No independent investigation has established those allegations as fact.
Downs subsequently advised Kaufman that an outside investigation and negotiations over Barroso’s departure could proceed simultaneously.
The commission therefore faces two separate questions: whether to pursue a negotiated separation and whether the city should independently examine allegations involving Barroso’s tenure regardless of whether he leaves.
If commissioners approve Lee’s resolution, Downs would be directed to report on the negotiations at the Oct. 1 commission meeting. The resolution does not identify an interim manager, establish a search process for Barroso’s successor or place him on administrative leave while negotiations proceed.
The item is scheduled for the commission’s 5:05 p.m. Tuesday meeting at City Hall, 1300 White St. and will be streamed live on the City website.














