Almost half (47.86 percent) of Key West’s registered voters showed up Aug. 18 to decide whether Sam Kaufman or Danise “Dee Dee” Henriquez would wield the mayor’s gavel for the next two years. When the 6,701 votes were certified, voters chose Kaufman with 57.59 percent over Henriquez’s 42.41 percent.
The last time we voted for a mayor was in 2022 and about 42 percent, or 6,094, of registered Key West voters cast ballots in race between Teri Johnston and Margaret Romero. Johnston won 56.24 percent to 43.76.
I’m not sure how much clearer the majority of Key West voters can be. Since November 2018, when three-term mayor Johnston was first sworn in, nearly 6 of 10 mayoral voters consistently hammered home these points: We’re not willing to sacrifice our quality of life to the pursuit of unfettered tourism, or to failing infrastructure, depleted environmental resources and developers bent on extracting cash from the island. We are not willing to swap One Human Family for “some exceptions apply.” And we’re not beholden to the legacy names that hold fast to birthright entitlements.
Even Johnston’s Republican predecessor, four-term Mayor Craig Cates, hewed mostly to the middle. He was a champion of affordable housing for older residents, environmental protection, One Human Family and quality of life for locals. Cates was named Key West’s Mayor Emeritus in 2018.
This past two-year hiatus when unelected Henriquez held the mayor’s position by default (she had no opponent, a fact due more to political chicanery than to disinterest by potential candidates), was no exception. Key West voters remained remarkably consistent in those messages, protesting by the hundreds when Henriquez and her commission majority capitulated to State of Florida threats over rainbow crosswalks, local police entanglement with Immigration and Custom Enforcement and Border Patrol, and water quality testing on top of rampant corruption and dysfunction in City Hall.
Though Kaufman built his campaign on the need for change, his success is rooted not so much in change as in a return to pre-2024 sensibilities — minus, of course, the criminal corruption woven into those years. Kaufman will face headwinds that Cates and Johnston could not imagine — and that Henriquez could not or would not navigate.
Say hello to the 10-letter word from hell: preemption.

Preemption: Trade rainbow crosswalks for a new hospital provider
Since 1968, when Florida voters extended home rule to cities and charter counties, the Florida Legislature has chipped away at local control. Gov. Ron DeSantis and his enablers raised preemption to an art form that could reach its apex in November when Amendment 3 — a poorly crafted Constitutional promise of lowered property taxes — goes before voters.
Even if Kaufman has a commission majority (which he doesn’t have yet and might not even after the November election), he can’t repaint the rainbow crosswalks, erect a rainbow arch on city property, stop the cruise ships cold, control development of the Outer Mole, forbid city cops from assisting immigration roundups or kick the developers out. That’s just for starters. He can’t mandate affordable housing at Key Plaza or stop open carry at our polling places.
If he tries, he’ll run smack into costly legal fights with the state, even if he wins. Kaufman will have to pick his battles very carefully to avoid squandering tax dollars in an already imperiled city budget, likely to get worse if Amendment 3 passes or if the city goes on an infrastructure binge that will cost millions of dollars in bonding debt service.
Kaufman’s smart, so I’m not telling him anything he doesn’t know. He’ll be far more nimble than Henriquez in navigating disappearing home rule and in negotiating the political compromises that are integral in conflicts. I’m not sure his voters understand just how limited the city’s options are for the most visible and controversial state mandates. Best to take a page from the Fence Fairy: Can’t paint your fence pickets? No worries. Add a mini-fence, that legal, colorful middle finger wagged at the haters.
But there are five things Kaufman can do. I hope to see these top on his early agenda.
(1) Get the Corradino Report in front of the full commission and the public and get that corruption mess cleaned up as the grand jury demanded. That includes making City Hall a good place to work — for real and not just in platitudes.
(2) Hire a qualified city manager and city attorney. It will take a commission majority, but Key West deserves and needs better than a good ol’ boy and his cousins and a contract lawyer from the mainland.
(3) Partner with Monroe County on the long-range Keys infrastructure study, which was given nod-approval to move forward on Aug. 19.
(4) Restart harbor water quality testing, and
(5) Bring us a new hospital provider. Kaufman’s the champion of this extraordinary grassroots project, which has largely been ignored by the Henriquez commission. In response to its Request for Proposals, Our Hospital Key West expects to hear from interested providers on Oct. 6.
As much as I’d like to see those rainbow crosswalks back at Duval and Petronia, I’ll trade them for 1, 2, 3, 4 and 5.
(Featured image photo of Sam Kaufman swearing in by Ralph De Palma.)





The loss of the Outer Mole was a true debacle! How did that happen? WHO “directed” the City Manager to negotiate with the Navy???? That was pure stupidity. Who did that benefit? Not the citizens. We already voted, as a City, we did not want MONSTER cruise ships. Votes don’t count? Let’s see what the island thinks about Port Key West. Let’s just see. It’s open season… Buses were not a priority. Giant cruise ships were.
Well stated!
great and honest take on the new mayor’s task and what has occured in the past!!! hoping for the best and his continued support from everyone