Delete. Delete. Delete.
The Key West mayor’s race tops my “back burner” list. That’s what I call those important-but-not-urgent things needing attention, just not today. Eventually I’ll get around to it, but for now, it’s delete, send to spam, scroll past.
As things stand now, on Aug. 18, either incumbent Mayor Danise Henriquez or longtime City Commissioner Sam Kaufman will win. But you can be forgiven if, based on your inbox, social media feeds and chats with friends, you feel like the election is tomorrow. I think we can let that pot simmer a bit and remember that a lot can change in four months.
I’m frequently asked why I haven’t written about the race. Same answer for decades: Most voters pay little attention to political campaigns until six weeks or so before they go to the polls. They sure aren’t agog here in March and April unless they’re part of the hardcore, partisan marketing machines that support the candidates.
I don’t know whether I’m voting for Henriquez or for Kaufman. Both are veterans of public life with productive career track records. Both are longtime islanders with their own deep-rooted constituencies. Neither has deal-breaking liabilities. But, wow, do they differ on this: One undershares. The other overshares.
That’s a problem.
Key West mayor’s race: What I hope to learn before August
Mayor Henriquez keeps her thinking so close to the vest that no onlooker can guess why she votes as she does. As mayor, she’s the last to vote during a City Commission roll call. Head down, sometimes with a long pause, particularly if it’s a controversial issue, she quietly says “yes” or “no.” No explanation. No context. Just a motivational void begging to be filled.
And filled it gets. Her detractors claim she’s told how to vote by unnamed right-wing, nefarious, big-development cabals. Then there are the rightly confused and angry voices after she shows up on the front line for a photo op and later votes against the same bloc’s interests. Since Henriquez offers no explanations for her vote-versus-photo-op decisions, speculation is unforgiving.
Like many of you, I got what appears to be the Henriquez campaign’s silly “how do you feel” survey. Those kinds of marketing surveys are ubiquitous. Anyone can crank them out. But from the reaction to the loaded questions in this one, you’d think (see above) cabals were at work. Let’s not waste our time getting overexercised.
For Key West’s undecided voters, including me, Henriquez’s failure to share more than her up-or-down votes can be a deal breaker. Before August, we need to hear a more forthcoming Henriquez. We need to know her values, politics and priorities — in context and with explanations. Silence, thinking it passes for neutrality, doesn’t cut it.
If by some miracle you don’t know where, why and how Commissioner Kaufman votes as he does, just ask. He’s likely to hold forth for 20 minutes and share a multi-page legal brief. He could give half his word allotment to Henriquez and have enough left over for two commission meetings. After his 10 years on the commission, we’ve learned we can take a bio break and not miss anything too important. Cuz he’ll reiterate. That’s Sam.
Looks like Kaufman’s running his campaign similarly. So much sharing. Lots of email blasts and social media posts. His early-season openness is a counterpoint to Henriquez’s reticence. It has the potential to fizzle. His diehard supporters won’t be swayed; they run his fan club. Undecided voters either aren’t paying attention or we’re turning away from the firehose.
Kaufman’s got a conundrum to answer before August. For five years or so, he has styled himself as the most aware, most experienced, most hands-on and most government-savvy commissioner.
Heck, he might be. And if he is, it raises this question: How could Kaufman not have at least heard the rumors about — and taken earlier action on — the corruption nightmare that resulted in criminal indictments against our former city attorney, chief building official and code compliance director? He sat on that dais with former Mayor Teri Johnston when those three were actively undermining city law.
Given the effectiveness of the Coconut Telegraph and his persona as the hyper-vigilant commissioner, Kaufman needs to explain. Either he’s not as plugged in as he says he is or he didn’t have the chops to expose the rot before the grand jury did.
Before Aug. 18, Henriquez needs to open up her shroud of inexplicable, baffling lack of rationales and Kaufman needs to explain how the smartest guy in the room appears to have been caught off guard by corruption that was likely table talk at lunch.
I’m shocked you think neither has deal-breaking liabilities.
(1) Henriquez was THE mayor during the corruption. Kaufman’s an attorney, and just one Commissioner, steeped in an objective mind and objectivity, by profession. Expectation he should act on “rumors” is reckless. Governance requires detail, data, and objectivity. Not “feelings” or “coconut telegraph” rumors.
(2) Henriquez showed up for the crosswalk photo, and voted NOT TO OPPOSE the crosswalk removal. Kaufman, opposed removal.
(3) Henriquez voted NOT to oppose the hateful 1101 / 1135 anti-diversity bills. Kaufman voted to oppose hate.
Any 1 of these 3 of these subjects, is disqualifying for another Henriquez term. Let alone 3 failures.
And, when Our Hospital Key West organized to bring more bidders to bid on our public hospital so we had a choice of suitors, versus status quo with the current operator for another 30 year lease, it took all of 3 minutes for him to say he’s all in. Since then, two years running, he’s fought for transparency along with us at every hospital district meeting, and together with his city task force, we were successful at making the next hospital operator lease competitive, with Baptist and Sinai vying for it too. Kaufman did this. Henriquez, as you say, remained quiet. In over two years of hospital commissioner meetings, only after the decision to make the process competitive, and public, nearly two years later, did Henriquez show up. Once. Like the photo op of the crosswalk.
It’s not an apples to apples comparison.
Kaufman, also known as Sam, saw the threat to our public hospital healthcare system and showed up day 1. Assembled a city task force to help Our Hospital Key West.
Kaufman fights, and votes, against hate and our ONE HUMAN FAMILY proclamation. Kaufman assembled, organized, and helped bring the decision to open our next 30 year Hospital lease to more hospitals, an achievement which will ensure the best sole hospital for our island, not just the status quo. This will affect the quality of our hospital for generations.
I’m with Sam, and you should be too.
Spencer, I don’t disagree with anything you say. Those points, which will weigh heavily, and how both candidates come forth over the next couple months will make my decision. I do want to clarify one point: Teri Johnston was mayor during most of the time frame of the corruption evidenced in the grand jury report. The grand jury considered evidence related to events between 2021-2024. Henriquez was sworn in on August 26, 2024. The grand jury issued its report in April 2025.
Until the City Commission voted to chop Al Childress off as City Manager,I paid more attention to the upcoming band list at the Parrot than I did to City politics.Never went to a Commission meeting.Knew Terri Johnson’s name but didn’t know my District 6 Commissioner from the chef at Santiago Bodega.
And I had never met Sam Kaufman.Shame on me.
Why didn’t Kaufman ring the bell on City corruption? Given some of the current decisions,even after the corruption scandal,by the Commission that seem to favor the same “unnamed,right wing ,nefarious big development cabals.”Why or how could he make a difference? At best he gets one vote to deter. the Gang of 5.
Heaven forbid I was on the City Commission,but would I have voted to renew the Conch Train Incoporated for 10 years,with 2 more years left in the current contract and then this week donated some of our most valuable real estate (Higgs and Mallory) to yet unknown and the Conch Train Corp again? Probably not.Maybe he tipped off the Attorney General But it looked to me like he didn’t need too.
As far as his hefty responses,I would rather have an ultra full response to issues that affect our City,than a nothing response.More information is better than less. I’m not an attorney and often don’t know the legal or political ramifications of an issue.And I’m old.I want someone ,except Attorney Smith,to explain it to me.
And speaking of saying too much, I am voting for openness,for full disclosure,for honesty and fairness’.I’m voting for Sam.
Kaufman did take action. But he was always in the minority throughout the 11 years. He voted no to fire Childress. He asked multiple times to have the Corradino Report discussed (which was the start of the corruption exposure). But city management wouldn’t put it on the agenda. That’s from sworn, under oath testimony to the FBI.
The problem isn’t Kaufman sitting back. The problem was a similarly corrupt Commission majority constantly hiding what was going on. They still hide it today and they lie about it.
Henriquez said at the meeting this week that the College cancelled the water quality testing. It’s a complete lie and she has said it multiple times. And so the cabal of a majority terminated the funding for harbor testing (Kaufman voted yes for the testing).
Finally we have a movement to allow a change of majority so Kaufman can get something done. The opposition against him are the people and organizations who want the status quo including the deep corruption that many, including me, have documented. Recognize that we are nearly a year into a recommendation by the Grand Jury that one commissioner resign because she is not fit for the job. Oh, by the way, she voted against funding the water quality testing this week too.
It’s way past time for a massive change. August 18th, 2026 is the day where it happens.
Open dialogue by politicians is essential. For that reason I would not vote for the incumbent.