Key West mayoral race heats up as filings reveal money, alliances

Money was the clearest early signal in Key West’s mayoral race: by March 31, City Commissioner Sam Kaufman had raised $115,245, outpacing Mayor Danise “Dee Dee” Henriquez, who had collected $68,890. The gap matters because Key West’s Aug. 18 election will decide not only the mayor but also commission seats in Districts II, IV and V, and the first campaign-finance filings showed which local blocs were moving fastest to shape the field.

Kaufman entered the race on Oct. 27, 2025 after representing District 2 since 2015, and his bid drew immediate support from former candidate Chris McNulty, who withdrew and backed him. Henriquez, who was automatically elected in 2024 when no one else filed, had already raised $51,695 in that uncontested campaign, a sign that this year’s contest is far more expensive and competitive. The city’s election materials say Key West voters will choose a mayor at large and commissioners from six single-member districts, with any runoff pushed to the national general election in November.

The donor lists show two distinctly Key West coalitions. Henriquez’s campaign drew support from prominent Conch families, business leaders and companies including Waste Management, Key West Theater and Rams Head, along with local professionals and restaurateurs. Kaufman’s filings included writers, architects, philanthropists, local restaurants and civic activists, including people tied to transportation, environmental and political causes. In a city where housing, tourism, development and basic city services drive daily politics, those names suggest the race is already reflecting deeper arguments over who should steer growth and who should pay for it.

The broader ballot is also crowded. Sarah Compton, Wayne Garcia and Juan Llera were running in District IV, while Keys Weekly reported no incumbents were running in Districts II, IV and V, leaving several seats open and the potential for late volatility. Under the city’s election rules, candidates seeking to qualify by petition had to submit signatures by noon on Monday, May 11, 2026. If no candidate clears 50% plus one on Aug. 18, the top two would move to a November runoff.

Monroe County had 54,550 active registered voters as of April 15, a reminder that Key West’s biggest political fights play out inside a relatively small electorate. With filings in hand and alliances already hardening, the mayor’s race has become an early count of money, organization and influence long before the first ballot is cast.