Key West Chooses Change

Key West voters decided they wanted something dramatically different Tuesday night.

City Commissioner Sam Kaufman defeated incumbent Mayor “DeeDee” Henriquez in one of the city’s most closely watched and hard-fought mayoral contests in recent memory.

According to results available on the Monroe County Supervisor of Elections website, at the time of this publishing, Kaufman captured 57.60% of the votes in what many speculated would be a much closer race.

But not, Kaufman. The candidate projected confidence in the weekend leading up to the vote and was convinced he would run away with the lead. He was astoundingly close in his estimates and proved much better at forecasting the size of his victory than many pundits who saw him eking out a narrow win.

The victory elevates Kaufman from the City Commission, where he served for more than a decade, to the mayor’s seat after a campaign built strikingly around one promise: change.

Change in the way City Hall communicates, makes decisions, and conducts public business.

"Yes, we will have change," he knowingly responded in an interview with MCTV.

For Kaufman, the result is more than just a promotion.

While some sources who worked at City Hall speculated that the commissioner had his eye on the top job well before last year’s announcement, the environment in which Kaufman launched his commanding bid for mayor seemed particularly suited to receiving his message about resetting Key West’s central hub of power.

Throughout the race, Kaufman repeatedly argued that residents had grown frustrated with inadequate communication, inconsistent decision-making, and a lack of accountability at City Hall.

A coalition that included progressives, moderate Democrats, Republicans crossing party lines, the LGBTQ+ community, snowbirds registered to vote here, first generation conchs, small business owners, environmentalists, and artists, seemed poised from early on to amplify this message.

Henriquez and her supporters, meanwhile, defended her record and argued that her experience, relationships, business background, and approach to governing were being undervalued and that without her, Key West could face an unpredictable future, particularly economically.

Tuesday’s vote suggests, however, that enough Key West voters were ready to try something different.

A Race That Got Heated

The mayoral race became increasingly divisive as summer wore on.

Supporters of the two candidates battled openly on social media, while arguments about development, city leadership, transparency, affordability, local identity, and the tone of Key West politics frequently ceded ground to personal attacks.

At times, supporters on both sides openly questioned why neither candidate appeared able to get their respective camps to turn the temperature down.

Countless mailers sent by outside groups claiming to support the mayor's re-election were a huge source of contention and may have ultimately cost her and turned off uncertain voters.

The intensity was unusual even by the standards of a small city that had seen its fair share of controversies play out in the public. After this election, it may be safe to assume that politics and City Hall have entered the realm of spectator sport.

Even while hoping, then expecting a Kaufman victory, voter John Petro felt uneasy. "

It feels like there is a lot of anger out there. I don't know if it just goes away."

Erin McKenna, who headed to the polls Tuesday, shared a similar concern. She expected roughly equal numbers of unhappy and happy islanders, with residents' social circles often filled with people who reinforced their own view of the race.

"There's gonna be no change unless we stop the divide," she said.

The Unpredictable Voters