The Key West Voters Making Both Sides Sweat

As Key West's race for mayor between incumbent "DeeDee" Henriquez and Commissioner Sam Kaufman heads into its final days, it continues to live up to expectations that it will go down as one of the hardest-fought mayoral elections in recent memory.

Both sides have had their share of fervent supporters taking to social media to blast their opponents in a race that, at times, became downright nasty. But that's politics in America in 2026. Though some might be surprised that that's also politics in Key West in 2026.

Throughout it all, there remained a very real wedge of undecided, cross-party, reluctant, and otherwise persuadable voters who were determined to cast a ballot in this race even if they weren't particularly enthused about either candidate or had to break from their traditional voting patterns.

For this story, I checked in with five of them as they discussed their criticisms, frustrations, praise, and ultimately what, if anything, either candidate could do in the final stretch to influence their vote.

All five opted to appear under pseudonyms so they could freely discuss the election without fear of rankling friends, colleagues, or patrons. All were committed to casting a vote. Sitting this one out was not an option.

An Unfortunate Vote

Sandra, a longtime transplant to the island who has traditionally supported moderate and liberal candidates, spent much of the campaign waiting for just a single good moment to decisively break for one candidate. Something that would give her a reason to back someone with enthusiasm.

That day never came.

While she wishes she could be all in for the incumbent mayor, who she thinks does represent stability in some ways, she also believes Henriquez has failed to visibly take action when it comes to "people issues" — matters of equality, immigration, and even City personnel.

As far as Kaufman is concerned, Sandra thinks he talks a good game but questions whether he really is a changed man. Her skepticism comes from familiarity with some of his prior professional dealings.

She described him in highly critical terms, at one point calling him "ruthless," while acknowledging that her impression of his professional life may not necessarily describe his political one.

After toying with the idea of sitting out the race, she decided against it.

"Oh, I'll vote, and unfortunately for DeeDee. I'd vote for Sam if I thought him believable."

"I'm Watching Who Candidates Align Themselves With"

Lacey, an islander with extensive professional and personal ties to the community, has also largely supported liberal-leaning and Democratic candidates throughout her life. Still, she has found this an especially frustrating race to watch.

"We have one candidate that presents as the school kid running for class president by promising 'pizza, more recess, and no homework,' and the other relying on voters to research facts, but not taking advantage of the opportunity to share more of themself," Lacey said, without specifying which candidate was which.

"We have to do better as voters," she added, stressing how important it was that locals resist the dog whistles that create anger and further division and avoid sharing "garbage" on social media.

"I'm watching who candidates align themselves with, and that is unfortunately contributing to more division," she said.

Beyond the obvious question of what each candidate says they stand for, Lacey wanted to know what evidence supported their records and what tangible results each could actually point to.

Weeks after we initially spoke, she decided to cast her vote for Henriquez. She felt Henriquez's track record of public service, bolstered by her history as tax collector, stood better than Kaufman's time on the dais.

"In comparison," Lacey said, "Sam has been in office for multiple terms as a commissioner and postpones dealing with issues. It appears he has paralysis by analysis."

Another deciding factor for Lacey was that Kaufman's years on the City Commission overlapped with the tenures of Ronald and Rajindhar Ramsingh, the City's former city attorney and chief building official, respectively, who were later indicted on multiple felony charges.

"DeeDee was not [in office]," she said of the mayor, who was sworn in two years ago in 2024, "yet has had to navigate the consequences."

The Less Sketchy Candidate

Mia, who works in the arts, describes herself as more uninformed than undecided when it comes to the mayoral race.

It is an interesting distinction, one she attributes to her ability to block out the, at times, avalanche of information that hits voters.

"I guess I never tuned in to it. I tend to ignore most political campaign stuff, be it texts, Facebook posts," she explained.

Mia believes there is almost always one candidate who is less bad than the other, and that is ultimately the person she will vote for.

At the moment, many of the people she considers her friends, who are active in the community, are supporting Kaufman. She isn't aware of anyone in her circle supporting the mayor. She's taking that as a sign that Kaufman may be the "less bad" choice in this situation.

But she still intends to read about both candidates' platforms before voting.

Specifically, Mia will be paying attention to their plans for affordable housing, curbing the presence of ICE, and determining who appears to be the "less sketchy" candidate when it comes to any histories of corruption.

"Like I said, least bad option."

When asked about her level of satisfaction with the mayor's first term in office, Mia acknowledged that things had definitely changed on the island but did not automatically lay those changes at the feet of Mayor Henriquez.

"Well, with the presence of ICE now and with our police force working with them, I'd say there has been a very significant change in the mood and actual makeup of the people in Key West. How much of that is to blame on the mayor, I'm not sure."

The Attack Ads Backfired

Tiffany, a more recent transplant who just launched her own small business, admits she is later than most in seriously looking into the election.

She attributes that, in part, to what she saw as a major rise in negative campaigning and attack ads.

"I am honestly just starting to look into it," she said. "I have a feeling I know how I'm leaning, but I need to do more research. When the smear campaign started I honestly took some distance from the race. Now I need to start getting involved again."

When Tiffany started receiving flyers in the mail and texts on behalf of Henriquez attacking Kaufman, she began to dismiss the contest as more of a "high school debate" than a legitimate race between people with real plans and priorities for the residents of Key West.

"Which was a pretty knee-jerk reaction and maybe unfair to all candidates," she confessed.

But to her, it felt inconsiderate to degrade the race into a smear campaign.

Despite her leanings, Tiffany's vote is still up for grabs. She would like to see more energy directed toward explaining plans for affordable housing and the implementation of a livable wage.

Even with just days left in the campaign, she urged the candidates to be more genuine with their messages.

"There will always be issues and not every goal can be reached, but having someone be understanding and honest about how they feel it's going — it can make it easy to trust them when tough calls need to be made."

A Conservative Impressed with the Other Side

Valentina, who seems to be constantly on the move tending to her entrepreneurial endeavors and side hustles, has typically voted Republican throughout her life.

Yet, when it comes to Key West's interests, she believes they are usually better served by having more liberal-leaning candidates in City Hall.

"I think Key West generally needs Democrats in office," she confessed.

She typically does not pay much attention to party when considering local politicians. City races are nonpartisan, in any event. But when she looks at the decisions being made for Key West, she finds herself more often siding with Democrats.

"The Republicans tend to be the Bubbas in Key West. On the flip side, in national elections, I tend to agree with the Republicans. Not on every issue — I actually like the environment and I'm good with LGBTQ+. Be who you are," she said.

She believes Kaufman has proven himself as a commissioner over the years, demonstrating a knack for researching and questioning issues, considering both sides, and voting for what she thinks has been best for the city and its constituents regardless of the politics surrounding a particular matter.

"I do not agree with many of the decisions DeeDee has made recently. And I do not appreciate the spam texts and the spam email I've received from DeeDee's side."

She thinks the surge of mailers and messages reflects a certain level of desperation by the mayor.

On the flip side, Valentina signed up for Kaufman's emails and has appreciated his updates as commissioner.

When asked whether she had any outstanding questions about Kaufman as the race tightened, she laughed after giving a decidedly simpler answer.

"No, I mean, I speed sometimes too."