Come August 2026, Key West voters will be asked to choose a mayor and a couple of city commissioners in three nonpartisan races that could be decided in the Aug. 18 primary.
Mayor Dee Dee Henriquez, who confirmed to the Keys Weekly on Oct. 28 that she plans to seek reelection to her second term, drew a challenger on Oct. 27, when City Commissioner and local attorney Sam Kaufman, who has represented District 2 on the city commission since 2015, filed paperwork to run for mayor.
Prior to Kaufman’s announced candidacy, resident Chris McNulty had thrown his hat in the ring in July, but told the Keys Weekly on Oct. 27 that he is withdrawing from the race to support Kaufman. McNulty’s candidacy was borne of frustration with the commission over their decisions about immigration enforcement and the rainbow crosswalks.
“Throughout these recent decisions at Key West City Hall, I witnessed Sam Kaufman consistently speaking up for the people of Key West, articulately fighting for our rights and sovereignty as an island community in the face of federal and state overreach,” McNulty said. “I firmly believe Commissioner Kaufman is the right person for the job of mayor of Key West….”
In addition to representing District 2 for a decade, Kaufman served as vice-mayor under former mayor Teri Johnston, from 2018 through 2024.
“Key West deserves leadership that listens, unites and works for everyone,” Kaufman said. “Our greatest strength is our people and I intend to bring the community together to face our challenges head-on with fairness, collaboration, and respect.”
He said his campaign will focus on consensus-building, transparency, fiscal responsibility and community participation.
“As a city commissioner and vice-mayor, Kaufman has provided steady leadership through some of the city’s most difficult years, including the COVID-19 pandemic and periods of major hurricane response and recovery, working to keep local government responsible and accessible,” states a campaign press release.
“During the pandemic and hurricane recovery, we learned what true community means,” Kaufman said. “Key West showed compassion, resilience and courage and I will continue to lead with those same values as mayor.”
Kaufman has also played a role in the ongoing process to select the next operator of the Lower Keys Medical Center, emphasizing transparency, stakeholder input and accountability to ensure the best outcome for local health care, the press release states.
“Our hospital is at the heart of our community,” Kaufman said. “We must make sure the next operator puts patients first, treats our local health-care professionals with respect, and provides the quality of care our residents deserve.”
“These past 10 years have given me a deep understanding of how our city works and, just as importantly, how it can work better,” Kaufman said. “I believe we can balance growth with preservation, fiscal discipline with compassion and progress with respect for what makes Key West unique.”
Kaufman’s campaign emphasizes unity and participation, building consensus across all parts of the community and ensuring that residents’ voices guide the city’s future.
Kaufman’s candidacy is not a complete surprise, as he previously considered a mayoral run before former Mayor Teri Johnston decided to run for a final term four years ago.
Mayor Dee Dee Henriquez ran unopposed in 2024 and succeeded Johnston.
Henriquez told the Keys Weekly this week, “Yes, I am running for re-election as mayor of Key West. Our city faced serious challenges and legal issues before I took office, and I’ve spent my term confronting them head-on. We’ve made real progress addressing those inherited issues, but the work is not finished — and neither am I. My commitment to the City of Key West and its people remains unwavering. I’m seeking re-election to see our vision through and to continue building a stronger, better Key West.”
For more information about Kaufman and his campaign, email Sam@KaufmanforKeyWest.com or visit KaufmanforKeyWest.com.
About Sam Kaufman
Sam Kaufman has been a resident of Key West for 27 years. His community involvement beyond City Hall includes:
• Serving as a mentor for the Take Stock in Children program
• Serving as an executive board member of the Key West Art & Historical Society
• Serving on the board of the Florida Keys SPCA
• Chairing the Florida Keys Outreach Coalition, where he has served for over 25 years helping individuals and families in need of housing, food and recovery services.
