KEY WEST, Fla. — City Manager Brian L. Barroso questioned Mayor Sam Kaufman’s sincerity Tuesday in an email distributed to all 402 employees of the city of Key West after the newly elected mayor called a special City Commission meeting that could determine whether Barroso’s contract is extended — or potentially terminated.
By 10 a.m. Tuesday morning, city employees were sharing screen shots of the communications all over the Island City, and Barroso — according to several witnesses in City Hall — stormed into Kaufman’s office, interrupted a meeting with another member of senior city staff and began verbally berating the Mayor.
In the initial email, Kaufman told Barroso that he had asked Assistant City Attorney Kendal Harden to draft a resolution formally preserving the commission’s right to reconsider the city manager’s employment agreement before the Sept. 7 deadline. Without written notice at least 120 days in advance, Barroso’s contract would automatically renew for two years on Jan. 7, 2027, with a 5% raise on top of his previously negotiated compensation.
THE EMAILS
Emails obtained and reviewed by Above the Fold establish a timeline for Barroso’s response:



The broad distribution elevated the temperature of what began as a contractual matter between the mayor, city manager and commission into a citywide confrontation just days after Kaufman took office.
In the original email sent at 9:30 a.m. as well as the secondary email to all city staff, Barroso said Kaufman’s decision appeared to conflict with a private conversation the two had Monday.
“Thank you for providing advance notice,” Barroso wrote. “I must express my disappointment with this decision, particularly in light of our conversation yesterday.”
Barroso said the conversation left him with “a very different understanding” of Kaufman’s intentions and the direction of their working relationship.
“Given this action less than a day later, I am left questioning the sincerity and accuracy of what was represented to me,” Barroso wrote.
Kaufman has called a special commission meeting for 4 p.m. Thursday to formally preserve the city’s right to modify or terminate Barroso’s employment agreement. The commission faces a looming contractual deadline: If the city does not provide notice at least 120 days before the end of Barroso’s current term, the agreement automatically renews for another two years.
“I meant what I said about putting past disagreements aside and working together professionally,” said Kaufman. “That commitment does not mean allowing an employment contract to automatically renew for another two years without review by the full Commission.
“Thursday's action simply preserves the Commission's options and gives all seven commissioners the opportunity to determine what is in the best interests of the City and our community.”
The proposed action would provide that notice without immediately terminating Barroso. It would keep the commission’s options open while preventing the automatic extension from taking effect.
But the meeting could go further. If commissioners express an interest in considering Barroso’s termination, the commission reserves the right to address the matter during the special meeting via an amendment to the resolution.
Barroso told the city’s workforce that Kaufman’s decision contradicted the mayor’s acceptance speech, in which Kaufman called for putting past disputes aside and working together to move Key West forward.
“Rather than providing the stability and fresh start discussed, this action only perpetuates uncertainty among City staff at a time when our organization needs clarity, consistency, and confidence in its leadership,” Barroso wrote.
Thus far the only two people facing instability and uncertainty appear to be Barroso and Downs.
Kaufman campaigned in part on changing the leadership and culture at City Hall, including replacing Barroso, dismissing Downs and hiring an in-house city attorney. His election shifted the balance of power on a commission that has frequently clashed with the city manager.
Barroso’s relationship with some members of the commission has been contentious since the administration of former Mayor Danise Henriquez. Those disputes have included questions about transparency, administrative authority and the city manager’s handling of commission directives.
BACKGROUND
BREAKING: Kaufman Calls Special Meeting on Barroso Contract
KEY WEST, Fla. — Mayor Sam Kaufman has called a special Key West City Commission meeting for 4 p.m. Thursday to consider providing City Manager Brian Barroso with the 120 days’ notice required to preserve the city’s right to modify or terminate his employment agreement.
Barroso acknowledged that the decision ultimately belongs to the seven-member commission and said he would reserve further comment until he reviewed the proposed resolution and consulted an attorney.
“In the meantime, I will continue fulfilling my responsibilities professionally and remain focused on the City, our employees, and the community we serve,” Barroso wrote.
The email provides the first public indication that Barroso believed he and Kaufman had reached at least a tentative understanding about working together before the mayor moved to protect the city against the automatic contract renewal. Barroso did not describe what Kaufman allegedly told him during their private conversation.
Barroso did not respond to a text for comment; Kaufman responded, but did not address Barroso’s characterization or severity of their conversations.
All three meetings will be streamed live on the city’s website.
This is an evolving story. Watch this space.
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