KEY WEST, Fla. — Sam Kaufman took the oath of office Monday as Key West’s new mayor, beginning a new era at City Hall after winning one of the most decisive mayoral victories in recent city history.
The ceremony represented more than a change in municipal leadership. Kaufman’s oath placed him in Key West’s history as the first Jewish person to serve as mayor and opened a new chapter for a city approaching its third century.
Kaufman was sworn in at noon in the commission chambers at Key West City Hall, completing his transition from District II city commissioner to the city’s highest elected office.
The Hon. Mark Jones administered the oath of office to Kaufman, who was accompanied by his wife and son.
The ceremony also welcomed two members to the Key West City Commission and three members of the Utility Board of the City of Key West.
Kaufman entered office on the strength of a landslide victory in the Aug. 18 election, defeating incumbent Mayor Danise Henriquez by more than 1,000 votes and 16 percentage points after one of the most contentious and expensive mayoral campaigns in city history.
Henriquez did not attend either the election night function at Harvey Government Center or the swearing in ceremony. District IV Commissioner Carey was also conspicuously absent, as commissioners Donie Lee and Aaron Castillo applauded from the dais.
Voters appeared to want change away from a regime that seemed to avoid transparency and openness — especially when it came to recommendations from two Monroe County Grand Jury reports highlighting failures in governance and organization under Henriquez and City Manager Brian Barroso.
Kaufman received 3,848 votes, or 58%, while Henriquez received 2,832 votes, or 42%, according to final election results.
The commanding margin gave Kaufman a clear mandate after a campaign dominated by concerns over city management, government transparency, affordable housing, development and public confidence in City Hall.
Another key item will be the selection of a new City Attorney if current part-time contractor and Orlando City Attorney Mayanne Downs is dismissed — which appears likely.
“I want everyone to know, that if you did or didn’t vote for me, we can work together. There has been so much division, and now I want to be able to work for every resident of the City of Key West,” Kaufman told Above the Fold. “We need to get back to One Human Family.”
Kaufman, an attorney who has lived and worked in Key West for roughly 30 years, begins his term facing major decisions involving city leadership, housing, development, transportation, the municipal budget and Key West’s relationship with the cruise industry.
The latest scandal to hit is a 44-page whistleblower complaint filed against the Key West Police Department by officer Dustin Christina.
During the campaign, Kaufman called for changes in city leadership and greater transparency from the municipal government.
His move to the mayor’s seat created an opening in District II, where voters elected former Commissioner Mark Rossi to return to the dais.
Rossi Returns to District II Seat
Rossi earned the chair after defeating Bobi Lore in the District II race.
Rossi received 256 votes, or 55%, compared with 206 votes, or 45%, for Lore.
The owner of Rick’s entertainment complex on Duval Street and former city commissioner, Rossi returns to the commission after previously representing District II roughly a decade ago. He succeeds Kaufman as the district’s representative.
“I just want to say that I am very, very humbled and want to thank the District II people that elected me, “Rossi told a near standing-room only crowd. “I want to do the best job that I can for everybody here and help bring consistency and clarity to City Hall and make sure that everybody’s voice is heard.”
Rossi joins a commission confronting major decisions involving the city budget, housing, transportation, development and the direction of the municipal government under a new mayor.
Massicotte Scores Commanding District V Victory
Christopher Massicotte also took the oath Monday as the new commissioner for District V after securing one of election night’s most decisive victories.
Massicotte defeated Waste Management’s Greg Sullivan by 14 percentage points, receiving 710 votes, or 57%, to Sullivan’s 535 votes, or 43%.
The commanding win followed an unusually bitter campaign in which Massicotte faced a sustained series of personal and political attacks. Voters nevertheless handed him a clear victory and a seat on the City Commission.
Massicotte succeeds Greg Veliz, who was appointed to complete the term of Commissioner Mary Lou Hoover following her death in November 2025.
“I want to thank all of the District V voters,” said Massicotte. “
Massicotte brings a new voice to the commission as the city begins another budget cycle and continues to wrestle with rising living costs, workforce housing and pressure on public services.
The victories by Kaufman and Massicotte represented two of the clearest outcomes in the city election. Both won by double-digit margins despite facing sustained opposition during the campaign.
One City Commission race remains unsettled. Sarah Compton and Wayne Garcia advanced to a November runoff for the District IV seat after neither candidate received the 50%+1 majority required to win outright Aug. 18.
Three Utility Board Members Sworn In
The ceremony also included the swearing-in of three members of the Utility Board of the City of Key West, which oversees Keys Energy Services.
Mona C. Clark took the oath for Seat A, Steve Wells was sworn in for Seat B, and Tim Urbanski took the oath for Seat D. Clark and Wells are Key West residents, as required for Seats A and B, while Urbanski represents one of two seats reserved for residents living outside Key West but within Keys Energy’s service area, which extends to the east end of the Seven Mile Bridge.
The six officials were sworn in at City Hall, 1300 White St., less than a week after voters cast ballots in the Aug. 18 election.
