Incumbent Henriquez and Commissioner Kaufman Launch 2026 Key West Mayoral Campaigns

Two established city leaders have moved the 2026 Key West mayoral race into active campaigning, sharpening contrasts over local governance and priorities that will shape city policy and services for voters.

Mayor Danise “Dee Dee” Henriquez, first elected in August 2024, formally kicked off her re-election bid with a campaign event held Saturday, Jan. 24. Henriquez announced her intention to seek another term in November 2025 and has since been running publicly across the island, including walking Duval Street during the Martin Luther King Day parade. She said, “She added that while progress has been made, there is still more work to do and she is seeking another term to continue those efforts.”

Challenging Henriquez is City Commissioner Samuel (Sam) Kaufman, who has represented District II since 2015 and served as vice mayor from 2018-2024. Kaufman, a Key West resident for 27 years, has framed his campaign around institutional reforms and broad civic participation. Kaufman said his campaign centers on “transparency, fiscal responsibility, inclusion and community participation.” His campaign website describes him as “an advocate for affordable housing, health care and working families.”

The field narrowed when former candidate Chris McNulty withdrew and endorsed Kaufman. The city’s active candidate list currently shows Henriquez and Kaufman as pre-filed for mayor; Chris McNulty is listed as withdrawn. Several other municipal contests are already active with pre-filed entries for commission seats in Districts II, IV and V.

Administrative rules and deadlines will play a decisive role in who appears on the ballot. Candidates seeking to qualify by petition must collect the required number of valid signatures - the mayoral threshold is 137 petitions - and submit petitions to the Supervisor of Elections for verification by Monday, May 11, 2026 at 12:00 PM. Petitions can be picked up at the Supervisor of Elections office. The city posts candidate lists and procedural information and provides public contact details at 1300 White Street, Key West, FL 33040; phone 305-809-3945; Email: Webmaster. Voter information, early voting dates, vote-by-mail guidance, demographic data and historical results are also available through county and city election resources.

Campaign activity to date has emphasized public appearances, fundraising and message development, but detailed policy plans and campaign finance disclosures have not yet been provided. Voters seeking to evaluate candidates should watch for platform documents, fundraising reports and full texts of kickoff remarks as campaigns accelerate.

For Key West residents, the contest will influence decisions on housing, municipal budgets, service delivery and how city government engages neighborhoods and visitors along corridors such as Duval Street. With the May 11 verification deadline approaching, Henriquez and Kaufman are moving from visibility events to the next phase of petition gathering, outreach and issue definition. Voters should monitor filings, review candidate materials, and use city election contacts to confirm ballot status and deadlines as the campaign unfolds.