Let’s be honest, when you think of Key West, you probably picture frozen margaritas, six-toed cats, and stunning sunsets at Mallory Square. And you wouldn’t be wrong. But lurking just beneath that sunny, postcard-perfect exterior is a wild, twisted history full of mafia bosses, haunted dolls, and international conspiracies.
If you want to know where the bodies are buried—literally and figuratively—you need to talk to David Sloan. He’s an author, storyteller, self-proclaimed “my-storyan,” and the guy who knows more about Key West’s quirky and dark past than pretty much anyone else on the island.
David recently stopped by the podcast (welcome back for episode 161!) to spill some serious tea on his latest research. We talked about everything from his groundbreaking book How Key West Killed JFK to a missing fire chief who dressed like a Santeria saint. Huge shoutout to iWitness Crime Tour for sponsoring this episode—if you love the stranger, true-crime side of Key West history, you definitely need to book a tour with them.
Grab a café con leche and pull up a chair. We are about to go down a massive Key West rabbit hole, and trust me, you are going to love every weird second of it.
From Ghost Tours to Great-Grandfathers
You don’t just wake up one day and become the premier ghost expert of the Florida Keys. David’s journey actually started in Scotland. After growing up in Texas and working in the hospitality industry on cruise ships, he took a Scottish ghost tour and had a lightbulb moment. People were actually making a living telling ghost stories. Um, yes please.
He quit his job, moved to Key West, and spent the last 30 years uncovering the island’s secrets. But the wildest part? It took him almost two decades of living there to realize he already had deep island roots.
His great-great-great-grandfather was part of the Pennsylvania 47th Volunteers, the Union regiment in charge of Key West during the Civil War. They actually built Fort East Martello—which ironically happens to be exactly where David spends a massive chunk of his time researching and running ghost tours today. Talk about the universe pulling you exactly where you need to be.
How Key West Killed JFK (Yes, Really)
Okay, let’s talk about the elephant in the room. When you see a book title like How Key West Killed JFK, your first thought is probably, “Is this a joke?” That is exactly what David thought when he first stumbled across the connections.
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He wasn’t even looking for Kennedy. He was looking for Bum Farto (more on him in a minute). But while digging through recently unredacted FBI and CIA files, he kept seeing Key West pop up in the JFK assassination documents.
We are talking about reports of Jack Ruby selling guns out of an Islamorada motel room. Lee Harvey Oswald fueling up a boat in Marathon and Stock Island. The director of the Key West airport, George Feraldo, even reported seeing Oswald and Ruby together at the airport waiting for a flight to Cuba. Feraldo’s wife Norma later confirmed to David that the CIA files on her husband were entirely true.
The Local Baker Who Might Have Changed History
David, who grew up in Dallas just 15 minutes from Dealey Plaza, realized he had to write this book. He didn’t want to write a crazy conspiracy manifesto with string and pushpins. He wanted to write a solid beach read about Key West’s role in the Cold War. But then he found Gilberto Policarpo Lopez.
Gilberto was a local baker in Key West who came over from Cuba in 1960. He is an actual suspect in the JFK assassination. The night Kennedy was killed, Gilberto crossed from Texas into Mexico, and the Mexican authorities flagged him as a suspect. The CIA and FBI completely downplayed his importance to the Warren Commission, only pursuing him after he was safely on a plane to Cuba.
The parallels between Gilberto and Lee Harvey Oswald are absolutely insane. They both left their wives right before the assassination, both were members of the Fair Play for Cuba Committee, and both got into public fistfights over Fidel Castro. David actually tracked down Gilberto’s daughter, who shared 60 years of hidden history, including the fact that her father admitted to being in Dallas the day Kennedy was shot. David even unearthed Gilberto’s passport photo, giving researchers the very first clear look at a major suspect.
The Mafia, the Teamsters, and Cold War Chaos
Why was Key West such a hotspot for all this drama? Simple: everybody operating in South Florida wanted Kennedy dead.
The CIA had a massive base in Miami and thousands of Cuban exiles furious over the botched Bay of Pigs invasion. The Tampa mafia, led by Santo Trafficante, was losing a fortune after Castro shut down their Cuban casinos. They already ran the “bolita” illegal lottery in Key West and trafficked heroin straight up the island chain.
Add Jimmy Hoffa and the Teamsters to the mix, who literally owned a third of the island (including the La Concha and Casa Marina hotels), and you have a powder keg of powerful people who all hated the President. History totally repeats itself, and reading about the missile drills and cold war paranoia in Key West is wildly fascinating.
Where in the World is Bum Farto?
Before David got sidetracked by the Kennedy assassination, he was hunting for the ultimate Key West legend: Bum Farto.
If you don’t know the name, Bum Farto was the Key West fire chief from 1964 to 1976. He was convicted of selling cocaine and marijuana out of the fire station, and shortly after, he vanished into thin air. He is basically the Jimmy Hoffa of the Florida Keys.
People love to turn him into a caricature. He wore head-to-toe red, sported rose-colored glasses, and draped himself in gaudy gold jewelry. But David’s upcoming book, Where Is Bum Farto?, sets the record straight. David uncovered that the cocaine conviction was likely a total setup—an undercover cop essentially bribed the jewelry-obsessed fire chief with a gold diamond ring.
More importantly, Bum wore red because he honored Shango and Santa Barbara from the Santeria religion. He was a powerful man who controlled fire in a town where the Tampa mafia regularly used arson as a weapon of distraction and intimidation. Understanding who he really was changes everything about why he disappeared.
The Beatles’ Unexpected Key West Vacation
Did you know The Beatles got stranded in Key West? In 1964, right at the peak of Beatlemania, a hurricane diverted their flight from Canada to Jacksonville. A press agent suggested they wait out the storm in Key West.
They stayed at the Key West Resort near the airport for 48 chaotic hours. David tracked down locals who shot pool with them and hung out in their hotel rooms.
But the island actually changed The Beatles, too. They were scheduled to play the Gator Bowl in Jacksonville, which was still racially segregated. While drinking in Key West, they refused to play unless the stadium desegregated—and Jacksonville caved. That trip also sparked a deeply emotional, tear-filled night of drinking between Paul McCartney and John Lennon as they processed the crushing weight of their sudden fame and the loss of their mothers. Paul even referenced it later in a song, asking, “What about the night we cried?”
Oh, and if Key West had an official Beatles theme song? David says it would definitely be “Here Comes the Sun.”
Robert the Doll Isn’t Evil (He’s Just Magic)
If you have ever Googled “haunted Key West,” you already know about Robert the Doll. He lives at Fort East Martello, and tourists are terrified of him. People claim he inspired Chucky (a total lie) and that you have to ask his permission to take a photo or he will curse you (also a lie).
David spent years reverse-engineering the Otto family legends and discovering Robert’s true origins. He is a Steiff doll made in the Black Forest of Germany, stuffed with “Excelsior” wood wool. According to David’s research, Robert isn’t a demon. He houses an elemental spirit tied to nature and the earth.
He is magic, not evil. If you approach him looking for a bad time, you might get one. But if you respect him, it is like he takes your hand and walks you through the dark forest, bringing you out a better person on the other side. You can actually meet him properly on one of Sloan’s Ghost Tours right inside the fort.
David Sloan’s Key West Hit List
You didn’t think I would let a 30-year local off the hook without asking for food recommendations, did you? If you are heading down to the Conch Republic, here is where David goes when he’s not chasing ghosts:
- Coffee & Breakfast: El Mocho on Stock Island. Order a café con leche (no sugar) and a plate of scrambled eggs and grits with hot sauce.
- Pastries: La Grignote. Their homemade croissants will change your life.
- Happy Hour: The Green Parrot. A total classic, no explanation needed.
- Dinner: Onlywood for incredible pizza, or hit up Hogfish Bar & Grill and Roostica on Stock Island for top-notch local flavor.
Frequently Asked Questions About Key West History
Is Robert the Doll really cursed?
No! According to David Sloan’s research, Robert the Doll is inhabited by an elemental spirit tied to nature, not a demonic curse. The rules about asking for his photo were completely made up by tourists over the years.
Did Lee Harvey Oswald visit Key West?
Newly unredacted government files show multiple reports of Lee Harvey Oswald being spotted in the Florida Keys shortly before the JFK assassination, including fueling up a boat and being seen at the local airport.
Who was Bum Farto?
Bum Farto was a flamboyant Key West fire chief in the 1970s who was convicted of drug trafficking before mysteriously disappearing. He remains one of the island’s most famous unsolved mysteries.
Are there still mafia ties in Key West?
During the mid-20th century, the Tampa mafia and the Teamsters union (including Jimmy Hoffa) owned massive portions of Key West real estate and ran illegal gambling rings. Today, it is mostly just a fascinating piece of local history.
Ready to Chase Your Own Key West Legends?
If this conversation didn’t make you want to immediately book a flight to the Florida Keys, check your pulse. The island is crawling with ghosts, spies, and secrets just waiting for you to uncover them.
To hear the full conversation and get all the juicy details, make sure you listen to episode 161 of the podcast. Do yourself a favor and pick up a copy of How Key West Killed JFK or The Key West Bucket List over at phantompress.com. And seriously, if you are visiting soon, book a spot on the iWitness Crime Tour to walk the exact streets where the mafia ran their numbers and legends went missing.
