No one pays much nevermind to what a small town with a meager 25,240 residents does. But when that tiny town welcomes more than a million visitors annually and when the Key West Mystique enchants millions more who simply wish they were here, well, folks pay attention.
So on June 30 when the City of Key West extended its collective middle finger to the state and national absurdity that is 2025 immigration policy — and I use that term loosely — trust me, millions listen. Tiny Key West, with its outsized clout and libertarian bent, took its slingshot and stood in all its legendary flip-flop, tank-top, frizzy-hair, out-of-my-face defiance and told Florida Gov. Ron DeSantis, his minions and ICE to, well, get lost.
The question is, though, will we have the same fortitude next week to stand up again to the bullying intimidation from the state? City Commission will meet in a second special session at 5 p.m., Tuesday, July 8, to vote on a resolution to formally enter into the 287(g) memo of agreement.
The new ICE resolution isn’t unexpected, and it’s likely a procedural necessity. The commission could vote as it did on June 30, a move that would make it absolutely clear Key West is standing firm against unwarranted state and federal overreach. But there’s also the danger that commissioners could endorse the agreement, voting “yes with a gun to our heads.” Understandable, I guess, since they face, as does Police Chief Sean Brandenburg, the governor’s threat to yank them from office.
Two of the seven commissioners won’t be at the meeting. Monica Haskell, who sponsored the successful June 30 resolution will be out of town. Sam Kaufman, who also championed the resolution, will be away, but will attend via Zoom. That means there will be six voting commissioners, including the mayor who is sponsoring the July 8 resolution. Without Haskell’s vote, defeating the resolution becomes more challenging.
I don’t like not having all commissioners in place to vote on something so important. It is what it is, and all the more important that the remaining commissioners hold fast.
This past Monday our commissioners did the right thing. Tuesday they will have to do it again. And perhaps again. There can be no fainting hearts if this island is to be more than a lackey for those destroying the state and national constitutions.
The ICE memo | The power of Key West clout
Here’s why it matters:
In the most stunning vote taken by a Key West City Commission in recent memory, commissioners voted 6-1, at 7:16 p.m., June 30, to void a 287(g) agreement with Immigration and Customs Enforcement.
Doing so put the city, commissioners and the police department squarely at odds with DeSantis’ mandate that all local law enforcement must agree to train and deploy their officers as ICE agents. Only Commissioner Lissette Carey voted to keep the agreement, signed on March 4, 2025, in place.
The resolution, which passed quickly with resounding affirmation from commissioners, brought cheers and applause from a standing-room only audience. Dozens of speakers during the public comment portion of the meeting hammered home the points that ICE activities on the island were unwarranted, overly aggressive and an affront the One Human Family culture that has made Key West a beacon for people seeking freedom, opportunity and community.
Threats of retaliation were swift. By midnight, less than four hours after the vote, Florida Attorney General James Uthmeier posted on X: “The City of Key West will be hearing from my office very soon.”
Uthmeier spent Tuesday high-fiving with DeSantis, President Donald Trump and Homeland Security Department Secretary Kristi Noem for the grand “soft” opening of a massive concentration camp in the Florida Everglades. The tent city will incarcerate in deplorable conditions upwards of 3,000-5,000 detainees, including children, until they can be deported. They call it Alligator Alcatraz. I prefer Kill The Glades Hater Gator Gulag. It’s more accurate.
DeSantis weighed in, too. The governor told reporters at the concentration camp opening that Key West officials could face suspension as a result of not upholding the agreement.
“I think the attorney general has weighed in on that,” DeSantis told the Miami Herald, “and I’ll let him do the analysis and send them whatever warnings need to be sent. But, the reality is, you have a responsibility for full participation. And, you can virtue signal and try to make political statements, but the reality is, local governments have to abide by Florida law.”
Then came “the letter,” the one Uthmeier sent to all commissioners on July 2 (well, except for the mayor whose name he missed. But who cares about details, right?). Uthmeier reiterated Florida’s threats: Get with the program or we’re gonna take over.
The ICE memo | After the euphoria, the real work begins
Here on the island there was no denying the jubilation rippling through the community over the defiant opposition to ICE depravity. It takes courage to do the right thing when going along would be the more pragmatic, if not also the more cost effective, path. After all, the governor has removed recalcitrant elected officials before, and Uthmeier makes no bones about threatening to relieve sheriffs and police chiefs of their duties, fine local governments and generally muck up their lives.
Commissioner Donie Lee, our former police chief, said Monday night he had come to the meeting “with a gun to my head” prepared to accept that the 287(g) memo of agreement would remain in place. But after listening to the residents, he said he would “make a decision from the heart and I hope it doesn’t get the city in trouble.” He then added his “yes” vote to the resolution, which was sponsored by Commissioner Monica Haskell and seconded by Commissioner Aaron Castillo.
The commissioners, buoyed on a wave of teal t-shirts emblazoned with “Immigrants Keep This Island Alive,” boldly chose One Human Family over Florida’s draconian, unholy alliance with a run-amok ICE. The power of community organization was triumphant.
The Key West Immigrant Support Network, which started less than a month ago with two women and snowballed into a juggernaut of businesses, churches, organizations and individuals, took up the heavy lifting of organizing the grassroots efforts that resulted in this commission meeting and its subsequent resolution.
But If you’re not appalled by the authoritarian, legally questionable usurpation of basic the American rights of due process and home rule, you’re probably not paying attention.
Key West is the miraculous dog that caught the car. We’re going to have to figure out what to do with it once the euphoria dissipates. ICE will remain on the island, likely ramping up as it tries to prove its toxic mission of fear and control. Our immigrant neighbors, those with and those without papers, 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 city and its taxpayers likely will face lawsuits and retribution. It’s one thing to say we’re prepared for the fight. It’s another when legal bills come due. And another entirely if a vengeful governor fires the commissioners and chief. I am, however, squarely with the speaker who on Monday said, “I’d rather pay more taxes for this than paying for corrupt officials,” a reference to payouts related to the terminations of three criminally charged city officials earlier this year.
On April 23, 1982, Key West seceded from the United States and formed the Conch Republic. It was a fanciful but defiant gesture, complete with Cuban bread and jolly times, that lasted one minute, followed by a declaration of war, a surrender and a demand for foreign aid. But a few days later the U.S. Border Patrol removed the unwelcome drug and immigrant interdiction roadblocks that were devastating Key West’s tourism. We celebrate each year with mock battles, conch fritters and toasts all round to island independence.
Monday’s defiance is born of the same libertarian — not liberal — gene pool. It is not, despite the governor’s say-so, “political theater.” We are Key West. We aren’t Monroe County or the Keys. We aren’t Florida. Heck, we’re not always the United States. We squabble among ourselves, live on island time, go along to get along, scrape together a living and periodically have to clean house to get city government unstuck from casual and criminal corruption. But don’t, don’t, mess with us.
Show up Tuesday, my friends. Ensure the commission and the chief know we’ve got their backs. Give them the cover they’ll need to once again prove One Human Family trumps a soulless government bent on replacing the American way with a dystopian world that once was relegated to apocalyptic fiction. Resistance begins at home.
Learn more
AG’s threat to Key West
KWISN call to action
KWISN legal opinion
- Key West 287(g) | The politicians caved. Could this be a good thing for the island?
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… Read more: Key West 287(g) | The politicians caved. Could this be a good thing for the island? - Key West ICE | The tiny island with outsized clout and a libertarian bentNo one pays much nevermind to what a small town with a meager 25,240 residents does. But when that tiny town welcomes more than a million visitors annually and when the Key West Mystique enchants millions more who simply wish they were here, well, folks pay attention. So on June 30 when the City of… Read more: Key West ICE | The tiny island with outsized clout and a libertarian bent
- Key West City Commission voids agreement with ICE and reaffirms its status as a “welcoming city.”In what is the most stunning vote taken by a Key West City Commission in recent memory, commissioners at 7:16 p.m., voted 6-1 to void the 287(g) agreement with Immigration and Customs Enforcement. Doing so puts the city, commissioners and the police department squarely at odds with Florida Gov. Ron DeSantis’ mandate that all local… Read more: Key West City Commission voids agreement with ICE and reaffirms its status as a “welcoming city.”
- Those tricky 287(g) ICE memos | Why didn’t county and city commissioners review them first?
I was baffled a couple weeks ago when friends and local officials seemed shocked that the Key West police chief and the Monroe County sheriff had signed 287(g) memorandums of agreement with federal Immigration and Customs Enforcement. Both had signed task force memos with ICE, agreeing to designate and train selected city and county officers… Read more: Those tricky 287(g) ICE memos | Why didn’t county and city commissioners review them first? - ICE in Key West | What you can do
Two Key West residents are petitioning Key West City Commission to clarify its policies and practices on local law enforcement working with ICE. Hundreds of local businesses, churches, pastors and Keys residents have already signed the petition. (Ranger Ed and I have signed as has Key West Island News. My church (Peace Covenant Presbyterian Church)… Read more: ICE in Key West | What you can do - Our disappearing e-bikes, or how ICE is changing Key West
The North Roosevelt Boulevard Promenade, that palm-lined, tourist-attracting raceway alongside the car lanes, is shockingly empty these days. Same is true along Staples Avenue, another e-bike path across the island. Gone are scores of locals on their e-bikes. They were easy to recognize. Destination-focused, wearing the branded uniforms of their local employers, ready for another… Read more: Our disappearing e-bikes, or how ICE is changing Key West
We want ICE to round up and deport ALL illegals. They are a drag on our community. No matter what paint brush you use, they are illegals and need to be deported.
Let stand firm.