The Key West Mystique

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7-8-25 City Commission Overflow

Key West 287(g) | The politicians caved. Could this be a good thing for the island?

Key West 287(g) | The politicians caved. Could this be a good thing for the island?

By Linda Grist Cunningham, editor and proprietor

Linda Grist Cunningham is editor and proprietor of Key West Island News and KeyWestWatch Media LLC. She and her husband, a park ranger at Fort Zach, live in Key West with their Cat 5s.
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07/11/2025

By now you know the Key West City Commission voted 4-2 on Tuesday, July 8, to enter officially into a 287(g) memo of agreement with Immigration and Customs Enforcement. That decision commits city police officers to being trained as and to act as ICE agents with the authority to arrest and detain for deportation people suspected of being in Key West illegally.

The vote upends the longstanding Key West law enforcement practice — in place under former Police Chief-now-Commissioner Donie Lee and, his successor Sean Brandenburg — of assisting ICE when called upon, but never proactively acting as ICE enforcement agents.

Commissioners surrendered the last vestiges of island home rule, endorsed the suspension of due process and placed political expediency ahead of basic human rights. They drove a wedge between our police and the people who now may fear to report a crime or help with investigations. Then they attempted to redeem themselves by voting to support a resolution to extend Temporary Protected Status to Haitians — but only after making absolutely sure that vote would have no effect except as a bit of political theater.

There was, I am sure, chortling and high-fiving up Tallahassee way. After all Gov. Ron DeSantis loves messing with Key West’s home rule, from overturning our cruise ship referendums to stripping the Tree Commission of authority. Attorney General James Uthmeier, fresh off his Everglades concentration camp tour, likes nothing better than flouting the courts and the law. He’s been held in civil contempt for ignoring a court order blocking a new Florida law that forbids anyone without legal status to enter or re-enter Florida. On Wednesday, the U.S. Supreme Court told Florida it could not enforce that law — at least for now.

Maybe there was a touch of disappointment. Those two would have enjoyed, I suspect, making Key West the poster child for what happens when one defies them. Had commissioners refused to sign, imagine the fun and red-meat headlines as DeSantis and Uthmeier sent in the Florida State Guard, the Florida National Guard, rallied for more ICE agents, plucked the dissenting commissioners off the dais, replaced the police chief and maybe even got the Commander in Chief down for a Key West sunset media op.

287(g)
Standing room only among the overflow crowd at City Hall on July 8. About 200 were in the main chambers and another 100 scattered throughout the building and outside.

ICE and 287(G) | Once for the heart. Once for the head

That commission vote rankles, though. A lot. I wanted commissioners to stand up to the governor and attorney general. I am tempted to conjure conspiracy theories and claim that if I were on that dais, I would have torn up the agreement. But, for now and until proven otherwise, I’m going to cut them a sliver of slack. Perhaps on June 30, they voted their hearts, and on July 8 they voted to keep state government from taking over our island with a sideshow and its pick of compliant replacements.

Commissioners Monica Haskell (on Zoom) and Mary Lou Hoover voted against the 287(g) agreement. Mayor Danise Henriquez and Commissioners Lissette Carey, Aaron Castillo and Lee voted in favor. Commissioner Sam Kaufman was out of the country and said he could not connect via Zoom. Had Kaufman been present to vote “no,” the result would have been the same: Key West sold out.

They didn’t have to. They could have postponed the 287(g) decision until the courts weigh in. While state law requires county sheriffs to sign on, no such law applies to municipal law enforcement. In fact, the Florida Legislature refused to take up bills this year that would have mandated municipal participation. The City of South Miami is seeking court clarification — and though Key West commissioners have said they support South Miami’s lawsuit, they declined to support a resolution to join. In short, all hat, no cattle.

Let’s go back a minute to that Temporary Protected Status for Haiti resolution. Estimates put the Key West Haitian community at about 5,000 and the mayor admitted there were city employees who could be affected — and then she voted “no” on the resolution. Unless a court intervenes, TPS ends Sept. 2 for Haitians and Cubans. After that, Haitians and Cubans with TPS status are fair game for ICE agents. So, yeah, a big deal.

What was so striking about that attempt at redemption was that commissioners and staff seemed to have little idea what TPS was about. To be fair, at least Commissioner Castillo did wonder aloud if the resolution ought not include other countries and Commissioner Haskell tried to help explain. But no one could come up with the other immigrant home countries at risk.

For the record, the Trump administration has suspended protective status for immigrants from Nicaragua and Honduras. Next up are Cuba, Haiti, Venezuela, Afghanistan, Cameroon and Nepal. Though court cases may slow deportations and those with green cards may be allowed to stay, the Department of Homeland Security is encouraging self-deportation: Get out now or we’ll kick you out.

It was a shocking lack of awareness, and one more example of commissioners’ failure to grasp current federal and state immigration policies. There’s nothing about today’s draconian immigration efforts that even marginally resembles “the way it used to be.”

The commission majority sent a two messages Tuesday night: “Hey there, Guv and AG, we’ll be good little boys and girls.” And then they said to our island, “We don’t have your backs. One Human Family? Not if you’re on the state’s gotta-go list.”

Commissioners may come to regret that unprincipled vote. Their decision solidified a new community leadership — a youthful, grassroots political force that could upend the current commission. Upwards of 300 smart, compassionate and determined locals overflowed City Hall. Few were the “usual suspects” who regularly come to city meetings. Of the three dozen who spoke for themselves and as representatives of churches, businesses and other organizations during almost three hours of impassioned public comment, only two sided with the commission majority.

There is work to be done. We’re going to have to figure out what to do once the grief over Tuesday’s 287(g) decision dissipates. ICE will remain on the island, likely ramping up as it tries to prove its toxic mission of fear and control. Our local police will be in untenable positions on the street. Our businesses are struggling. We all know that, even if few are speaking aloud. Our neighbors, those with and those without papers, even those with U.S. citizenship, remain in jeopardy, living in such ceaseless fear that they stay hidden rather than reporting for the jobs vital to the island’s success.

The next generation of Key West leaders was in that room Tuesday night. They give me hope that this is the catalyst for a dramatic shift in who runs this island. If I were a commissioner afraid of losing my job to Tallahassee threats, I’d be more concerned about what happens come next election.

Read my earlier posts on ICE and 287(g)

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