The Key West mayor’s race is getting ugly as accusations fly, investigations open and campaign ethics complaints surface. It could make for an interesting city commission meeting on Thursday, June 4.
The recent mudslinging appears to have started on May 21, when City Manager Brian L. Barroso sent commissioner Sam Kaufman, who is challenging incumbent Mayor Dee Dee Henriquez for the mayor’s gavel, a lengthy email with the subject line, “Use of City Hall and City Resources by your campaign.” Barroso also copied the two city attorneys on his email to Kaufman.
In his email, Barroso describes a situation that allegedly occurred on Dec. 26, 2025, a day on which city hall was closed due to the Christmas holiday.
“Based on a recent Citizen’s complaint, the City has reviewed building access records, security camera footage, and internal IT documentation,” Barroso writes. “Those records show that on Friday, December 26, 2025, a day on which City Hall was closed to the public for the holiday, you entered the building by requiring a City employee to provide you access, even though that employee had the day off. You attempted to use your security badge, issued to you in your capacity as a city commissioner, to access the building, but you hadn’t renewed it, so it didn’t work. You were accompanied by individuals who are not City employees and who had no independent authorization to be on the premises.”
Barroso alleges that Kaufman and another individual accessed city hall and the commission chamber to film a campaign-related video. In so doing, they allegedly moved the nameplates that identify each commissioner’s and the mayor’s seats on the dais.
Barroso writes that the nameplates were not returned to their original positions and that the “dais veneer” had been visibly damaged, requiring “several hours” of staff time to restore.
“A political advertisement promoting your candidacy has since been published depicting footage filmed inside the commission chamber,” Barroso’s email states. “In that footage, the dais nameplates are shown turned backward in precisely the condition staff discovered them on December 30, and a non-City videographer is plainly visible. No person with authority to do so, including me, approved the use of the commission chamber to produce campaign material, the after-hours entry of non-City personnel into City Hall, or the handling of City equipment for those purposes.
“That this appears to have occurred through your unauthorized (and inappropriate) use of a city employee, who you requested travel to city hall to let you in makes this a serious matter,” the email states.
Barroso then lists portions of state statutes pertaining to candidates’ use of government resources for campaign purposes, including:
- “Section 106.15(3), Florida Statutes, prohibits a candidate from ‘using the services of any state, county, municipal, or district officer or employee during working hours’ in furtherance of his or her candidacy.”
Kaufman told the Keys Weekly that city hall was specifically closed that day and was not used during working hours.
In his email to Kaufman, Barroso demands that Kaufman submit a response within 10 business days, which would be Friday, June 5.
On Monday, June 1, Kaufman emailed Barroso acknowledging receipt of Barroso’s initial email. “I also note that, despite your statement in your May 21, 2026 correspondence directing that I respond within ten business days, you elected today to publicly release substantive communications and allegations regarding this matter prior to expiration of the deadline you established,” Kaufman wrote. “That decision raises additional concerns regarding fairness, impartiality and whether this process was truly intended to allow for a good-faith response before public dissemination.”
In his email, Kaufman denies “any violation of law, policy, election laws, ethics rules or damage to city property.” Kaufman also requests from Barroso a list of items, including security footage, notice that was provided to commissioners about a security update that would have rendered Kaufman’s access badge to city hall unusable, the identity of the person who made the complaint about the December incident, estimates for the cost of alleged repairs to the dais and access logs.
“Given your stated intention to potentially refer these matters to outside agencies, or discuss them publicly, I respectfully request that the requested materials be provided as soon as reasonably possible. … Further, given the pending mayoral election, and my status as Mayor Henriquez’s current opponent, I respectfully request that any review, referral or public discussion of these matters be handled in a neutral, evidence-based, and politically impartial manner, and in a way that avoids even the appearance of selective enforcement or use of city processes for political purposes.”
Then what happened?
On May 26, Key West resident Marilyn Kellner, a Kaufman supporter, emailed a letter to city attorney Mayanne Downs, outlining her concerns about the city’s social media accounts being used to “unfairly promote Mayor Henriquez and her reelection campaign.”
Kellner describes “hundreds” of social media posts that prominently feature the mayor, and no other commissioners, at ribbon-cuttings, events, announcements, ceremonies and photo ops.
One specific social media post on the city’s and the police department’s Facebook pages that Kellner describes promoted a Memorial Day event at a city park. “The post expressly promoted the reelection of Mayor Dee Dee Henriquez and stated the event was paid for by her political campaign.”
Kellner asks the city attorney to look into the matter to ensure that city resources are not being used for political purposes.
In her response, Downs reminded Kellner that by virtue of the mayor’s elected position, she would naturally be expected to appear in social media posts about city events.
Downs also writes that an internal IT investigation revealed that no city personnel had posted the message in question, and said there had been a “cybersecurity breach” that had been reported to the FBI for further investigation.
“Mayor Henriquez had no involvement and did not authorize the posts,” Downs wrote.
Ethics complaints
Kellner’s letter to the attorney prompted Kaufman to file ethics complaints to the Florida Commission on Ethics against Barroso and Henriquez, alleging they have used, or failed to prevent the use of, city social media resources “in a manner that has disproportionately benefited Mayor Henriquez and her reelection campaign.”
When asked about the situation, Henriquez told the Keys Weekly, “As for the city manager’s investigation into matters at City Hall involving Commissioner Kaufman, I have no comment at this time.
“Regarding the ethics complaint filed against me, I view it as no more than petty politics born out of desperation. I am fully confident that the Ethics Committee will conclude that I have complied with all election laws and ethical standards in my role and capacity as mayor. I welcome a thorough review of the facts and am confident that this complaint will ultimately be found to be without merit.”
Pending questions
The Keys Weekly submitted the following follow-up questions, and was told by city spokeswoman Alyson Crean that the city does not comment on pending investigations.
- May we request the result and findings of the internal IT investigation into the recent cybersecurity breach?
- How is it known there was a cybersecurity breach?
- May we request the communication that the city of Key West sent to the FBI, alerting the FBI to the cybersecurity breach?
- Did the breach affect any other city accounts, emails, websites or social media pages? Or was the Memorial Day post the only thing targeted in the cybersecurity breach?
- Is there a mechanism in place whereby city commissioners can submit photos of themselves at community and city events for possible inclusion on the city’s social media accounts?
- Who manages the city’s social media accounts? Who decides which events get covered, and which photos get posted on the city’s social media accounts?
- Is there a city policy pertaining to the city’s social media accounts? If so, I’d like to request a copy of the policy.
