Ed. Note: There is a difference between Republican’s and MAGA supporters, just as there is between Democrats and Communists. This isn’t intended for three out of the four user groups.
KEY WEST — We were somewhere around the intersection of politics and golf cart fraud on North Roosevelt Boulevard when the code enforcement letter kicked in.
Tom Crane — a Tinley Park, Illinois, transplant who showed up in Key West, opened a jeep rental lot at 3424 N. Roosevelt Blvd. and apparently decided the island’s political landscape needed his particular brand of suburban Chicago scorched-earth warfare — has built himself a little media empire surrounded by a moat of bile.
His crown jewel is stopthepython.com, a website so unhinged it should come with a prescription. The entire operation exists to destroy District V City Commission candidate Chris Massicotte, whom Crane has rechristened “Python Christos Massicottus”(sic) — the man’s name Latinized like a species classification, the banner draped over a doctored photo of City Hall with a serpent slithering across the front lawn.
You cannot make this up. But Crane can. And does. Daily. See for yourself by clicking on the image below and be sure to checkout Cucko, err I mean Crane’s fan mail:
He is a featured speaker at the Southernmost Republican Club. His Facebook page is a monument to paranoid political theater — every post tagged to the rafters with Republican clubs, candidate pages and enough hashtags to crash a server.
He champions Mayor Henriquez, District IV candidate Juan Llera, District II candidate Mark Rossi and District V candidate Greg Sullivan — whether they want the public bear-hug of a man who posts memes for a living or not.
The targets of his fork-touched wrath?
Mayoral challenger Sam Kaufman. Massicotte. District IV candidate Sarah Compton, whose personal Instagram posts from a European vacation Crane screen-grabbed and weaponized into a political dossier accusing her of hating America, Christians and the Fourth of July. And District II candidate Bobi Lore.
He occasionally lauds common-sense District IV candidate Wayne Garcia — who likely wouldn’t touch that with a 10-foot paintbrush.
But Massicotte gets the full frontal treatment — the website, the Latin name, the snake imagery. The man devoted an entire domain name to calling a City Commission candidate a reptile.
That takes a special kind of commitment, the kind that happens at DePoo Hospital and comes with a brand-new pair of nonskid brown socks (IYKYK.)
The Golf Cart Problem
Who ever said God (if you believe in her) doesn’t have a sense of humor?
Because here is the beautiful, rotten irony at the center of this whole den of vipers: While Crane was busy hunting pythons on Facebook, the City of Key West Code Enforcement was hunting him.
On July 9, Code Compliance Officer Alma Montano — after a routine internet investigation, the kind where somebody in a city office Googles your business and finds out you’re advertising services you’re not licensed to provide — dropped a four-count Notice of Code Violation (Case CC2026-02149) on KWJA, Inc., Crane’s corporate entity. Four counts. Like a grand jury return for a man who rents jeeps.
Key West wasn’t conquered by pirates, hurricanes, or developers. It was slowly suffocated beneath an endless tide of wheezing rental golf carts, each one buzzing like an angry refrigerator with a learner’s permit. The legal operators are bad enough. The outlaw fleet has turned the island into an amusement park where every intersection feels like the opening scene of a low-budget disaster movie, and somehow everyone has agreed to call it “transportation,” like the electric wheel chairs used by the elderly as a primary mode of transport to Publix.
The charges:
Count 1 (Sec. 18-354): Operating golf cart rentals without the required recreational rental vehicle permit. Crane’s business tax receipt covers jeeps. Period. Not golf carts. Not mopeds. Not scooters. Jeeps. And yet there they were, golf carts plastered all over his website, ready to rent, no permit in sight.
Count 2 (Sec. 18-355): No conditional use approval. You want to rent golf carts in Key West? You go before the Planning Board. Crane did not.
Count 3 (Sec. 18-351): Failure to register his rental fleet. Every operator must file serial numbers with the city annually. Crane did not.
Count 4 (Sec. 18-359): No city identification decals on the vehicles.
The penalty: $250 per day per violation. $500 for repeats. Unpaid fines become liens on your property. The kind of math that makes a man reconsider his career as a political blogger; maybe golf carts don’t suck.
Crane’s response, posted to Facebook — because that is where all serious legal disputes are adjudicated in the 21st century (other than Truth Social) — addressed “Mr. Montano.”
He misgendered the code officer. The letter was signed by Alma Montano (alma.montano@cityofkeywest-fl.gov, 786-697-6756). The irony of a Red Hatter — such staunch defenders of one gender identity per person — likely eludes them.
Crane declared his attorneys had reviewed the matter and the planning department had concluded “we have no problem with anything Mr. Crane is doing.”
The city’s four-count violation notice begs to differ.
The Competitor He Is Undercutting
This is not some harmless paperwork snafu. Crane’s unlicensed golf cart operation puts him in direct, unfair competition with legally permitted businesses — businesses that paid for their permits, went before the Planning Board, registered their fleets and stuck the city’s decals on every last cart.
Businesses like HydroThunder of Key West, which has been doing it by the book since 1994 — and which has donated $2,000 to Mayor Henriquez’s campaign across two entities.
Read that again.
The mayor’s self-appointed political hit man, née python hunter, is undercutting one of the mayor’s own big financial supporters by renting golf carts outside the law. I am half-way surprised he didn’t try to say that Python massicottus had learned to use a pen, conquered the English language and slithered into 1300 White St. to fill out a code complaint form.
If this were a novel, the editor would send it back. Too on the nose.
The Money Behind the Mud
Crane is not the only weapon in the Henriquez arsenal. He is the loudest. But the most dangerous operation runs quieter and carries a much bigger wallet.
Families & Friends for the Keys is a political action committee that has carpet-bombed Key West voters with unsolicited attack texts and glossy four-color mailers savaging Sam Kaufman. The shadowy PAC is chaired by Jack Niles — the former standout Conch jock, auto dealer, devoted Henriquez loyalist and one of KW baseball’s most enthusiastic athletic supporters.
As Above the Fold first reported, Historic Tours of America the multi-state trolley and tour empire owned by Ed Swift and partner Chris Belland, bankrolled the PAC with an opening $10,000 — more than 95 percent of its total receipts at the time.
The money kept coming.
The Spottswood family — likely the Keys’ most entrenched real estate and development dynasty, whose holdings stretch from Fleming Street to the horizon — opened their checkbook for $15k.
Hollywood-based developer Jeffrey Cornfeld who bamboozled another city commission — a longtime ago in a Key West far, far way — dropped another $10,000. Cornfeld is the man behind the Peary Court fiasco — the deal where a previous City Commission handed him $12.5 million to buy the property, he promised affordable housing and 44 new units, and Key West got neither. Now he is bankrolling the effort to keep the status quo alive. Surprised? You shouldn’t be.
Planning Board member Michael Browning serving his third consecutive appointed term on the very board that oversees land use and development in this city, contributed $500.
Marathon realtor Denise Holland Schmitt sent $520 from 50 miles up the road. Stock Island restaurateur Bobby Mongelli (Roostica Wood-Fire Pizzeria; Hogfish Bar & Grill) kicked in a modest $250.
Here is where the numbers get interesting: the PAC has collected more than $36,000 in contributions but reported a grand total of $21.10 in expenditures — an electronic processing fee.
Twenty-one dollars and ten cents.
Meanwhile, pissed off voters are having their phones blow up with inflammatory, libelous texts about Kaufman while their mail boxes overflow with professionally designed four-color glossy mailers.
These things do not write, design, send/print or mail themselves.
Under Florida Statute 106.19, any PAC officer who knowingly fails to report expenditures commits a first-degree misdemeanor — up to a year in jail, a $1,000 fine per count and a civil penalty of three times the unreported spending.
That is not a suggestion. It is not a guideline. It is not a grand jury recommendation.
It is the law.
The Big Lie
Mayor Henriquez has spent months pushing a public narrative that the negativity in this election is coming from the other side — from Kaufman, from the reform candidates, from the people trying to make a difference and clean up 1300 White St. rather than preserve its rotting furniture.
The facts in evidence tell a different story entirely.
The attack texts that voters could not stop? Niles’ PAC. The mailers? Niles’ PAC. The website dedicated to calling a commission candidate a snake? Crane — a Henriquez supporter running an outlaw golf cart rental operation on a street where the other rental shops actually follow the law.
Kaufman has publicly pledged not to go negative. So have the other candidates.
Henriquez has not disavowed a single text message, a single mailer, a single post from Crane’s digital fever swamp or any of Nile’s dirty baseball.
The silence is the tell.
Tonight, all of the candidates that Crane has been doing the heavy lifting for, have the opportunity before the League of Women Voters and a passionate electorate to do so. In the words of Nancy Reagan in betweeen bottles of amphetamines and a healthy Screwdriver poured with a heavy hand, “Just Say No.”
Oh, except for one. Mayor Henriquez won’t be there tonight, supposedly, because her schedule conflicted with truth, honesty and transparency.
The Juneteenth Question
And then there is this.
Circulating in Key West political circles is a racist Juneteenth screed posted June 19 under the name “Tom Crane” — a stomach-turning rant invoking fried chicken, watermelon, “greens and grits” and calling the federal holiday “dumbas” and “another racist holiday that some dumb f---ing demcrat thought was a great idea.” The post exhorts readers to vote against “any dumbass Democrats” in November.
It cannot be confirmed that this post belongs to the same Tom Crane who operates Key West Adventures at 3424 N. Roosevelt Blvd. But a search of that name on the social media platform returns the post tied to a profile bearing it, and the rhetorical fingerprints — the political tags, the candidate shout-outs, the raw and unapologetic tone — are disturbingly familiar.
If it is the same man — and even if it isn’t, everything that came before is reason enough — the candidates who have accepted his public support have a decision to make. And the clock is ticking.
Voters head to the polls Aug. 18.
At this point, nothing would surprise me. Maybe Python christos massicottus learned how to type with no arms, no hands, no fingers and created a fake FB account just to attack the renegade rental agent.
It is Key Weird, after all.
Ed. Note: This content is not affiliated with, authorized by, endorsed by or produced on behalf of any candidate, campaign or political committee in Monroe County.
