Key West voters elected a new mayor on Aug. 18, choosing longtime city commissioner Sam Kaufman over incumbent Dee Dee Henriquez, who was seeking a second term.
Though Key West city elections are officially nonpartisan, the divide between Republicans and Democrats was apparent, and Democrats carried the night, winning three of the four city races. Mark Rossi, a bar owner and former commissioner, is the only Republican who won, having defeated Bobi Lore for the District II seat.
In addition to Kaufman defeating Henriquez, Chris Massicotte handily beat Greg Sullivan in District V, and in District IV, the two Democrats — Sarah Compton and Wayne Garcia — are heading to a November runoff. They both earned more votes than Republican Juan Llera, but neither secured 50% plus one vote, which was needed for an outright win. (See page 9 for details on the commission races.
Kaufman dominates after contentious campaign
Predictions of the outcome varied wildly among local politicos and armchair strategists. In the end, the race was not particularly close. Kaufman received 58% of the vote, compared to Henriquez’s 42%. Of the 6,680 votes cast, Kaufman received 3,848 while Henriquez got 2,832.
The campaign divided Key West for nearly a year, as supporters on both sides turned Facebook into a pit of grievance and ridicule. A political action committee raised more than $25,000 from prominent businessmen to support Henriquez by attacking Kaufman with inflammatory mailers, TV commercials and letters to the editor.
The Key West Chamber of Commerce also supported Henriquez, endorsing her and the other three Republicans — Rossi, Sullivan and Llera — despite never having endorsed candidates before in its 100-year-plus history.
The support wasn’t enough to give Henriquez a second term, and Kaufman will be sworn in before the end of the month along with newly elected commissioners Rossi (District II) and Massicotte (District V).
The District IV race was narrowed from three candidates — Compton, Garcia and Llera — to two. Compton and Garcia, both registered Democrats, will face each other in a November runoff. The current commissioner in District IV, Lissette Carey, will remain in place until after the November election.
Kaufman said after his win that the aligned slate of candidates was an intentional strategy, “because I knew if I were elected mayor, that’s just one vote. It’s not enough to make change and get things passed.”
In an interview after his victory, Kaufman reiterated his position that the current city manager, Brian L. Barroso, is not the right person for the job.
“We have these divisions now … but we’re going to get past that,” Kaufman said. “I don’t hold grudges against anybody. It’s not about grudges. It’s not personal. But we need the person that can help lead city staff, bring the commission together and do it in a way that is more effective than what we have now.”
Finally, Kaufman spoke to Henriquez’s supporters, saying, “If you supported Mayor Henriquez and you feel like there’s something important that we can work on and we can partner together, I want you to come to City Hall. I want us to partner. I don’t care what your politics are. I want to know that we’re aligned on an issue and we can partner and we can improve that for our community. That’s what I want.”
Henriquez had not released a statement as of 6 a.m. Aug 19. Her campaign’s Facebook page was also unavailable at that time. She did not stop at the Harvey Government Center on election night, where several candidates awaited the results and were interviewed.
Key West City Races (winner’s name is in bold)
Mayor
Dee Dee Henriquez
Sam Kaufman
City Commission, District II
Bobi Lore
Mark Rossi
City Commission, District IV (November runoff election)
Sarah Compton
Wayne Garcia
Juan Llera
City Commission, District V
Chris Massicotte
Greg Sullivan
