Editor’s note: A full recap of Mayor Sam Kaufman’s first press conference will be published tomorrow.
KEY WEST, Fla. — Mayor Sam Kaufman called Wednesday for an independent investigation of City Manager Brian L. Barroso, citing what he described as months of intimidation, workplace misconduct, questionable representations to the City Commission and potential interference with elected officials.
Kaufman announced the request during his inaugural weekly press conference, attended by Above the Fold, Keys Weekly, The Keys Citizen and other media outlets.
“The public, city employees and every member of the City Commission deserve to have the facts concerning the City Manager available to them,” said during the presser.
The request marks a significant escalation in the conflict between Key West’s newly elected mayor and its chief administrative officer.
It came less than a week after four commissioners rejected an effort to preserve the city’s right to modify or terminate Barroso’s employment agreement before an automatic-renewal deadline.
BACKGROUND
BREAKING: Barroso Questions Kaufman’s Sincerity and Accuracy in Citywide Email
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.
Kaufman said his concerns extend well beyond the heated dispute over Barroso’s contract.
“These concerns did not begin last week,” Kaufman said. “Serious issues involving the City Manager have developed over a period of months. Some involve documented events or matters I personally witnessed. Others involve allegations or unanswered questions that require independent investigation.”
Kaufman explained to members of the press why he was releasing the information now:
“I believed the responsible course was to allow a reasonable period for that possibility to be explored rather than publicly escalating the situation,” he said.
“No separation agreement has been reached.”
Kaufman said he therefore believed transparency was now the better course.
“I am releasing my September 1 and September 2 memoranda, together with my September 3 statement, so that the public, City employees and members of the City Commission have the information necessary to evaluate these issues for themselves.”
Above the Fold was the only local news outlet to previously report extensively on the contentious issues between Kaufman and Barroso before the mayor publicly called for an investigation.
A ‘Fit Of Rage’
Kaufman’s request follows an Aug. 31 meeting with Barroso which went well according to both, then a Sept. 1 meeting that the mayor described in a contemperaneous memorandum and a subsequent addendum on Sept. 2.
Kaufman said Barroso flew into a “fit of rage” during the meeting and made statements including calling him a “child,” “coward,” saying their working relationship was “all out the window. He also said that Barroso yelled “if you think you have the four votes, terminate me.”
Those statements, Kaufman believes, raised questions about Barroso’s temperament, professionalism and ability to continue working effectively with the city’s elected leadership.
Kaufman’s description also echoed complaints from city employees about Barroso’s temperament and management style.
According to employees within City Hall who experienced Barroso’s wrath and filed complaints with the city’s Human Resources Department alleging a toxic work environment, workers began using the phrase “going Barroso” to describe such encounters.
Kaufman did not coin the phrase, but did say the reasons outlined are precisely why a review removed from Barroso’s control and the city’s administrative chain of command is necessary.
Human Resources is not a charter position and reports directly to the city manager and could potentially be too politicized. It was unclear at deadline if an outside investigator could be engaged — like the Florida Department of Law Enforcement, detectives from the Monroe County Sheriff’s Office or the State Attorney’s Office.
Among the recommendations in the initial grand jury report that led to the felony indictments of former City Attorney Ron Ramsingh, his brother, former Chief Building Official Raj Ramsingh, and Code Enforcement Director Jim Young was that the city hire an independent inspector general or auditor.
A majority of the former City Commission, however, declined to act on that recommendation.
A Laundry List of Concerns
Other than personal interactions following his landslide victory over former Mayor Danise Henriquez, Kaufman outlined a host of other issues and questions that he believed should be investigated, including:
Threats of Arrest and Intimidation: “While I was serving as a City Commissioner, I received multiple email communications from the City Manager accusing me of criminal conduct and urging me to ‘self report,’” Kaufman wrote. “There was never a legitimate claim of criminal conduct.”
Kaufman said that during their Aug. 31 meeting, Barroso told him that the city attorney had instructed him to send the communications and indicated that he was not acting of his own volition.
Cybersecurity Breach Representations: The city manager represented to the City Commission that a cybersecurity breach had occurred in connection with posts made on City and Key West Police Department social media pages promoting a then-Mayor Danise Henriquez campaign event.
“Law enforcement has since concluded that no cybersecurity breach occurred,” said Kaufman. “This leaves important unanswered questions: What was the factual basis for telling the Commission that a cybersecurity breach had occurred? What investigation had occurred before that representation was made? And once law enforcement determined that no breach occurred, why was the Commission not clearly informed and the record corrected?”
BACKGROUND
BREAKING: Kaufman Files Ethics Complaints Against Mayor, City Manager Over Alleged Use of Public Resources
KEY WEST, Fla. — City Commissioner and mayoral candidate Sam Kaufman has filed ethics complaints against Mayor Danise Henriquez and City Manager Brian Barroso, alleg…
Commission Dais Allegations: Barroso accused Kaufman of causing damage to the dais while filming campaign content. “Questions remain concerning how those allegations were developed, investigated and communicated,” he said.
BACKGROUND
BREAKING: Kaufman Denies Allegations, Seeks Evidence in Dispute With City Manager
KEY WEST, Fla. — An email obtained and reviewed by Above the Fold shows that Key West City Commissioner and mayoral candidate Sam Kaufman formally denied allegations raised by City Manager Brian Barroso concerning the alleged misuse of City Hall facilities and city resources, while demanding the release of evidence supporting the claims before any furth…
Access to City Staff: Kaufman said that after he took office on Aug. 27, he received an email directly from the City Manager informing the Mayor’s Office that permission from the City Manager’s Office was required before he or the Mayor’s assistant met with City staff.
Kaufman said that the basis and authority for this restriction, who it applies to, and whether it has been applied consistently should be determined.
Access to City information: “During a recent budget review meeting with the City Manager and senior staff, the Finance Director offered more than once to provide me with written materials responsive to questions I was asking,” said Kaufman. “I personally heard the City Manager respond that he had instructed her not to send those materials to me.”
Whether information responsive to requests from elected officials has been withheld, under what circumstances, and pursuant to what authority or policy should be reviewed.
Employee Morale and Workplace Concerns: “Current and former City employees have communicated concerns to me regarding management and the working environment at City Hall,” Kaufman said. “I am not presenting those concerns as established facts. They should, however, be taken seriously enough to determine what the evidence shows.”
Kaufman said that he believes relevant exit interviews, employee complaints and other available information should be independently reviewed to determine whether there are recurring workplace or management concerns and to fairly assess the current state of employee morale.
Creation of City Departments: “The City Manager established or designated a Growth Management Department and a Licensing and Permitting Department without a vote of the City Commission,” said Kaufman. “I recently asked City legal staff whether the City Manager had the legal authority to create these departments without Commission approval. As of the date of this statement, I have not received an answer. The legal authority for these organizational changes should be determined.”
Personnel Decision Requiring Investigation: “I have received information indicating that an individual hired by the City Manager may be related to him,” Kaufman wrote. “That employee subsequently resigned but, according to information provided to me, continued working for the City after allegations of fraud had arisen.”
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KEY WEST, Fla. — Another management-level resignation has added to growing scrutiny and turmoil surrounding the City of…
Kaufman said that he had not yet independently established those facts, but as in the other instances of possible conduct and misfeasance, that an independent investigation should determine whether there was:
A familial relationship
What role the City Manager had in the hiring and continued employment of the individual
What allegations were known to management and when
Whether applicable City policies and laws were followed.
Barroso was previously removed from the Board of the Florida Keys Aqueduct Authority for similar conduct— resulting in the appointment of the late, longtime board member Cara Higgins — before eventually being cleared by the state ethics commission.
Kaufman said an investigator should determine the nature of any relationship between Barroso and the individual, Barroso’s role in the hiring or continued employment and what city management knew about the alleged fraud.
2026 mayoral election: “A witness has provided information alleging that the City Manager approached or encouraged individuals to become candidates for Mayor during the 2026 election,” wrote Kaufman. “I am not presenting that allegation as established fact, but again believe it should be independently investigated.“
Commission Authority and Policy Decisions: This has been a huge issue of contention for Kaufman since Barroso was hired.
“There have also been concerns regarding significant City policy matters being decided, communicated or implemented administratively without appropriate consideration or authorization by the City Commission,” he wrote. “One matter warranting review involves decisions concerning the Outer Mole. The Commission and the public should know what decisions were made, by whom, what authority existed for those decisions, and whether matters requiring Commission approval were brought before the Commission.”
BREAKING:Navy Terminates Key West Mole Pier Lease After Months of Growing Tension Over a Lack of Cruise Revenue Repairs
KEY WEST, Fla. — The U.S. Navy has formally terminated the City of Key West’s lease agreement for use of the outer Mole Pier at Naval Air Station Key West, escalating a growing d…
Taken together, however, Kaufman said they raise legitimate questions concerning the accuracy of information provided to the Commission, access by elected officials to City employees and information, employee relations, significant administrative and policy decisions, and respect for the respective responsibilities of the City Manager and the elected City Commission in addition to clarity and transparency for the public.
“The purpose of that investigation is not to validate my concerns or reach a predetermined result,” said Kaufman. “It is to determine the facts.
“The investigation should include review of relevant emails, text messages, records and other communications and interviews of individuals with firsthand knowledge,” he went on. “It should also include relevant personnel policies and records, organizational changes, employee exit interviews and complaints, and policies or directives concerning elected officials’ access to City employees and City information.”
Kaufman said that he believed where decisions were made concerning significant City policy, organizational structure or personnel, the investigation should determine who made those decisions, what authority existed for them, and whether applicable City policies, ordinances, the City Charter and other legal requirements were followed.
“The investigation should follow the evidence wherever it leads, including evidence that supports or contradicts any allegation.
Two Separate Questions
“The first is whether the City Manager and the elected leadership of the City can maintain the professional working relationship, communication and trust necessary to effectively operate City government.” he said. “The second is what the facts establish concerning the additional matters described in my briefs.
“Those questions deserve a fair and independent investigation.”
Kaufman said that the events of September 1 events were particularly significant to the first question.
“The City Manager told me that our discussion about working together was “all out the window,” told me to terminate him if I had four votes, and shortly thereafter our regularly scheduled weekly meetings were cancelled,” said Kaufman.
Barroso did not attend the press conference on Wednesday.
“Those are facts that the City Commission and the public are entitled to consider,” said Kaufman. “I am not asking anyone to simply accept my conclusions.
“This is not about a personality conflict. It is about whether City government can function effectively, professionally and transparently; whether elected officials have the information necessary to perform their responsibilities; whether City employees are being treated appropriately; and whether the respective responsibilities of the City Manager and the elected City Commission are being respected,” said Kaufman.
“The people of Key West deserve the facts, and they deserve a City government they can trust.”
This is an evolving story. Watch this space.
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