BREAKING: Henriquez seeks second term; District II’s Kaufman to challenge in 2026 Key West mayoral race
The mayor, tied to the island’s Conch and Chamber of Commerce establishments, seeks reelection amid fallout from a grand jury probe that brought 21 felony indictments under her watch.
Mayor Danise Henriquez said Friday she will seek a second term, setting up a 2026 mayoral contest against District II City Commissioner Sam Kaufman, who announced his bid earlier this week.
The nonpartisan primary is Aug. 18, 2026.
Kaufman, who has represented District II since 2015 and served as vice mayor from 2018 to 2024, is campaigning on consensus-building, transparency, and fiscal responsibility.
Henriquez, who represents an old-guard, Conch-led and Chamber of Commerce affiliated political movement long tied to Key West’s traditional power structure, took office in 2024.
Shortly after taking office, the city began reeling from a sweeping grand jury investigation by the Monroe County State Attorney’s Office.
That probe resulted in 21 felony indictments against former City Attorney Ron Ramsingh, his brother and Chief Building Official Raj Ramsingh, and longtime Code Enforcement Director Jim Young.
The resulting grand jury report delivered a stinging rebuke of City Hall, alleging backroom deals, mismanagement, and an overall lack of transparency at 1300 White Street.
While Henriquez campaigned on restoring public trust and reforming internal operations, her administration has since found itself mired in the fallout of those indictments and the continuing perception of opaque governance.
Despite the controversies, Henriquez has highlighted several achievements during her first term, including advancing long-stalled infrastructure projects such as the Duval Street Revitalization and Resiliency Project and awarding a long-delayed water-quality monitoring contract — which has yet to be finalized by the dais.
The 2026 primary is scheduled statewide for Aug. 18. If no candidate wins a majority in the mayor’s race, a runoff would follow on Nov. 3, 2026.