Billionaire Private Island Tier List: The Wildest Flexes Money Can Buy

Billionaires Buying Islands: A Totally Normal Hobby...Right?

Welcome to the only tier list that matters: The Billionaire Private Island Flex-Off. Because when you've got more money than moral restraint, what do you do? You buy your own chunk of Earth, of course—and some go harder than others.

F-Tier: "Why Did You Even Bother?"

Paul Allen’s Island (Allen Island, WA)
Bought for $8 million in 1992, it’s not even named after him. No amusement parks, no robot butlers, not even a volcano lair. Just a regular ol’ patch of land. For a tech guy, this was giving "Ctrl+Alt+Nope."

John Lennon’s Hippie Experiment (Dornish Island, Ireland)
Lennon got a deal: 19 sad little acres for $2,000. Populated it with 25 hippies who quickly realized acid doesn’t keep you warm. They dipped after two years. Yoko Ono flipped it later for 30 grand. Imagine buying an island for less than a used Honda.

C-Tier: "You Tried, Bless Your Heart"

Tyler Perry’s Half-Finished Dream (White Cay Bay, Bahamas)
Bought himself an island for his 40th birthday (as one does). Imported palm trees from Miami like it was a Pinterest DIY project. Still under construction… 15 years later. We’re calling this the “Madea Builds a Mansion” saga.

Ted Turner’s Turtle Hangout (St. Philip’s Island, SC)
Bought in ’79, it’s basically a nature preserve with one house and some hiking trails. He saved endangered turtles, so we’ll give him eco-points. But for a man who founded CNN, this island lacks breaking news energy.

B-Tier: "You're Rich, But Are You Branson Rich?"

Craig McGaw’s Anti-Millionaire Power Move (Vancouver Island, Canada)
Bought 780 acres to stop millionaires from building on it. Then he built his own mansion, airstrip, and a fake Wild West town. It’s like saying “no loud parties” and then throwing a full-blown rodeo.

David Copperfield’s Real-Life Disneyland (Musha Cay, Bahamas)
The magician bought 11 islands like it was Monopoly, then turned Musha Cay into a custom adventure park. For $57,000 a night, you get cast members acting out storylines. It's like LARPing, but with caviar.

A-Tier: "Next Level, But Still Earth-Based"

Larry Ellison’s Lanai Takeover (Hawaii)
Oracle’s co-founder bought 98% of Hawaii’s sixth-largest island and then built an eco-wellness tech resort that makes you wear sensors and eat based on your biometric data. It’s a little Black Mirror, but the golf course is probably amazing.

Jiri Smej’s Maldives Paradise (Velaa Island)
Didn’t know anything about hospitality, but still turned this into one of the most exclusive resorts on the planet. You can rent the whole island for $1.3 million a night—cheaper than Twitter, more peaceful than Elon’s X feed.

S-Tier: "Insanity? Nope. Just Peak Billionaire"

Dietrich Mateschitz’s Fijian Hideaway
Red Bull’s co-founder hated people so much, he bought an entire island to hide on. Eventually he got bored and built a luxury resort with its own submarine and airstrip. Dude drank 12 Red Bulls a day and died chillin’ on a beach. Respect.

Richard Branson’s Necker Island (British Virgin Islands)
Bought it for $180,000 because he was trying to impress a girl (spoiler: it worked). Now it’s a $100 million celebrity playground with flamingos, imported art, and a 10-bedroom villa. He literally built a space company and a supermodel vacation club from one romantic flex.

Larry Page’s Nature Guardian Collection
Not to be outdone, the Google guy just bought five islands—didn’t even build on most of them. Why? To protect endangered species. Rich enough to buy islands just to leave them alone. Now that’s serene boss energy.

D-Tier: "The Cringe Billionaire Bracket"

The Barclays' Evil Villain Arc (Sark, English Channel)
These twin billionaire brothers went full "Island Bond Villain" mode—built a gothic castle, tried to secede from the UK, created their own flag, and got slapped by the UK Supreme Court. This isn't island ownership. It's colonial cosplay.

Stephen Deckoff’s “Rebrand from Hell” (Little St. James, USVI)
He bought Jeffrey Epstein’s old islands. Plans to turn them into high-end resorts. Not sure how many piña coladas will erase that history, my dude. Might wanna sage the island first.

Honorable Mention: Aristotle Onassis—From Friendzone to Honeymoon

In 1963, Onassis went from dating Jackie Kennedy’s sister to marrying Jackie herself after buying a Greek island and glamorizing it with sand, villas, and charm. If islands could talk, Scorpios would drop tea.

Billionaire Island Ownership – Flex or Fail?

Some billionaires buy islands to escape. Some build utopias. A few just collect them like Pokémon. Whether it's to impress a date, protect turtles, or start a “spa-slash-health cult,” these islands tell us one thing: insane money leads to even more insane decisions.

But hey, if you ever hit that Powerball jackpot, maybe you can be the next island overlord. Just don’t forget the flamingos.