Jeffrey Epstein and a Brief History of the Billionaire Sex Island

Wealthy child sex offender Jeffrey Epstein may have avoided a long and ugly trial by dying in his jail cell — no doubt you have your own theory about how that happened — but the bizarre and creepy details of his life have unraveled a secretive world that goes well beyond his own crimes. At the same time, we continue to learn more about what Epstein was up to: working contacts with prestigious universities, running a “sexual pyramid scheme” through a modeling agency, figuring out how to inseminate as many women as possible at a New Mexico “baby ranch,” etc.

Yet Epstein is probably most synonymous with Little St. James, his 70-odd-acre Caribbean hideaway among the U.S. Virgin Islands. The place has come to be known as “Pedophile Island,” “Orgy Island” and the “Island of Sin,” and most reports bear that reputation out. In addition to the rumors and horror stories surrounding the tropical enclave, there are cult-like touches to on-site developments that were enough to raise alarm: both a massive sundial and a blue-striped cube building (initially topped with a golden dome), whose purpose no one has been able to explain, make the place look like a set for the next season of True Detective. 

This week, we got a better understanding of how Epstein had bought a second private island, Great St. James Cay, despite the previous owner’s reluctance to deal with a known sex trafficker. It involved using the name of a royally connected Dubai businessman — who had forbidden him to do so — as a cover identity in the $22.5 million deal. Almost simultaneously, we learned that the prime minister of Lebanon, Saad Hariri, had given $16 million to a South African bikini model he met at The Plantation Club, an exclusive resort in the Seychelles, a remote archipelago country in the Indian Ocean, north of Madagascar. The model, along with others, had been recruited at age 19 to travel to the club — according to the New York Times, “passports were taken when they arrived and they were forbidden from taking photos.” 

All this had people asking, “Does every mega-rich guy have some kind of sex island?”

While anyone in the market for their own island these days has the advantage of online realtors specializing in such properties, these private oases were a hot commodity even in pioneer days. Fisher Island, a man-made island off Miami Beach that now claims the highest per capita income of anywhere in the U.S. — many members of the only-accessible-by-boat retreat are millionaire tax refugees — is named for Carl Graham Fisher, the entrepreneur who snapped it up in 1919, when the mainland coast was still a mangrove swamp. He then traded it to William Kissam Vanderbilt II, an heir of the prominent shipping and railroad family, for a luxury yacht. By 1963, Fisher Island had fallen into the possession of another group of elites that included former Vice President Richard Nixon.

Now, do I believe that everyone who at some time owned the island (or a stake in it) used it as some kind of fuck pad? I wouldn’t venture to speculate, since we can’t really confirm such details — which you’ll agree is probably the point. We’ll never know!  

Looking at the celebrities currently known to have private islands doesn’t inspire much confidence, either; you wouldn’t relish a night in their company, let alone miles away from civilization, surrounded by shark-infested waters. The magician David Copperfield, who has a chain of 11 islands in the Bahamas, last year stood accused of drugging and sexually assaulting a teen model in the 1980s. Alleged domestic abuser and all-around loose cannon Johnny Depp also has a spot in the region. I can’t imagine feeling safe on Mago, Mel Gibson’s island in Fiji. I’d be surprised if Nic Cage even remembers buying Caribbean real estate. Supposedly, Leonardo DiCaprio is turning his island in Belize into an “eco-resort,” to which I can only say… sure, that’s a thing. Why not take the leader of the Pussy Posse at his word on that one. No, I’d be far more comfortable staying with Tyler Perry.  

See, as ever, how Oprah is the reasonable one here. The woman is worth billions, but does she go around waving a red flag by bidding on uninhabited sandbars beyond the reach of state authority? Of course not! She simply invests in a grand estate on a lovely island where other people also live. Anything more extreme is for the ego-driven freaks like Virgin founder Richard Branson, who a musician has said abruptly motorboated her cleavage during a party at his famous Necker Island compound. And just to remove all doubt that going after one of these lonely pieces of land is the sign of an unwell mind: Donald J. Trump tried, in the 1990s, to acquire Davids Island, off the coast of New Rochelle, New York, losing a $500,000 deposit in the process. More recently, his daughter Ivanka was said to be interested in the amusingly named Rat Island, near the Bronx’s City Island. 

It’s the colonizers of this sort who put you in mind of the ethics-violating vacation Canadian prime minister Justin Trudeau enjoyed on an island owned by the Aga Khan, a billionaire royal — or, to pick a chilling case with parallels to Epstein’s, the story of Francis Shelden, a millionaire who ran a pedophile and child pornography ring on North Fox Island, between the two peninsulas of Michigan, through the 1960s and 1970s. As owner of the island, he’d had an airstrip built there and flew kids in on the pretense of hosting a nature camp, and though he would go on to escape justice, his activities have since prompted theories of a link to a series of child murders in Oakland County, Michigan. Who knows what Mark Zuckerberg could get away with if he seals off a few hundred more heavily guarded acres of property on the Hawaiian island of Kauai, or if Peter Thiel thinks he’ll be king of New Zealand after the apocalypse. At the very least, these incursions would seem to demand a wealth tax, but let’s not mince words: should you “need” a private island, it’s certainly not for anything good.  

So credit to Céline Dion, who said au revoir to hers, paving the way for another loaded Quebecois to start throwing Eyes Wide Shut masquerades there. We always knew you were better than that!       

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Miles Klee

Miles Klee is MEL’s resident tank-top dirtbag, shitposter and meme expert. He’s also the author of the novel ‘Ivyland’ and a story collection, ‘True False.’