Diamonds. Superyachts. Entire islands. A ticket to space. Somebody actually paid for every single one of these — ranked most expensive first, in every category.
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The five diamonds that turned an auction paddle into a nine-figure decision.
Cut from a rough stone the size of a golf ball, the largest internally flawless fancy vivid pink diamond ever graded sold in under ten minutes.
The largest fancy vivid blue diamond ever to reach auction sold to a phone bidder at Christie's Geneva.
An 18.96-carat fancy vivid pink diamond, kept in the same family for generations, sold to jeweler Harry Winston Inc.
A 12.03-carat internally flawless blue diamond, bought by tycoon Joseph Lau and renamed for his young daughter.
A 24.78-carat pink diamond, locked away in one family's vault for 60 years, before it ever reached an auction floor.
The five vessels that turned "boat" into a nine-figure understatement.
Built for Roman Abramovich, Eclipse is widely reported as the most expensive yacht ever built — a private vessel armed like a small warship.
Built for the family of the UAE's late president, Azzam held the title of the world's longest yacht for years — longer than a football field and a half.
Built for metals billionaire Alisher Usmanov, Dilbar's onboard pool alone reportedly holds enough water to fill several backyard pools combined.
Built for Sheikh Mansour bin Zayed Al Nahyan, Topaz stretches 482 feet and was, for a time, chartered out at roughly $2 million a week.
At 446 feet, Flying Fox is one of the largest charter yachts in the world, with a beach club, spa, and garage space for jet skis and mini-submarines.
The five islands billionaires bought outright instead of renting a beach house.
Oracle co-founder Larry Ellison purchased nearly the whole of Hawaii's sixth-largest island, all 141 square miles of it, in a single deal.
Shipping magnate Aristotle Onassis's legendary private island, site of his 1968 wedding to Jackie Kennedy, changed hands decades after his death.
Illusionist David Copperfield purchased this private Bahamian island chain and turned it into one of the world's most exclusive rental retreats.
Red Bull co-founder Dietrich Mateschitz bought this Fijian island as an undeveloped plantation and rebuilt it into one of the most expensive resort islands on Earth.
Branson bought Necker as an uninhabited scrap of land in the British Virgin Islands, decades before it became his signature private retreat.
The five aircraft that turned commercial-grade jets into billionaire-only real estate in the sky.
A bare Boeing 747-8 airframe runs roughly $400 million; once outfitted with a private owner's custom cabin, the total bill often exceeds half a billion dollars.
Prince Alwaleed bin Talal commissioned a private Airbus A380, the largest passenger jet in the world, reportedly fitted with a concert hall and a garage for his cars.
One of the world's wealthiest monarchs outfitted a personal Boeing 747 with finishes more commonly seen in palaces than airplanes.
Several Gulf royal families and billionaires have converted Boeing 787 Dreamliners — designed for commercial airlines — into ultra-private long-range jets.
Gulfstream's flagship business jet is the go-to aircraft for tech billionaires and hedge fund managers who want the best without a full widebody conversion.
The five private residences where "house" stopped being the right word.
Indian billionaire Mukesh Ambani's personal residence is widely reported as the most expensive private home ever built.
This French Riviera estate, built by King Leopold II of Belgium for his mistress, has repeatedly been floated on the market at a price no other private home has matched.
The largest home ever built in the U.S., a 105,000-square-foot Bel-Air megamansion, collapsed into bankruptcy before finally selling far below its ambition.
Bill Gates's Lake Washington estate took years to construct and remains one of the most technologically advanced private homes ever built.
Industrialist Ira Rennert built one of the largest private residences in America on New York's exclusive East Hampton coastline.
The five paintings that turned brushstrokes into nine-figure decisions.
This depiction of Christ, attributed to Leonardo da Vinci, shattered every auction record and has not been publicly displayed since.
Willem de Kooning's abstract expressionist masterpiece sold in a private transaction to hedge fund manager Kenneth Griffin.
Paul Cézanne's series of card-playing peasants includes this version, reportedly sold privately to Qatar's ruling family.
Paul Gauguin's Nafea Faa Ipoipo, painted during his time in Tahiti, sold in a private deal reportedly brokered for Qatar's museums.
Jackson Pollock's Number 17A, a hallmark of his signature drip technique, sold privately to the same collector who bought Interchange months earlier.
The five vintage cars that turned collecting into a nine-figure sport.
One of only two ever built, this 1955 racing coupe was sold directly by Mercedes-Benz itself in a closed-door sale.
This Ferrari 250 GTO, one of just 36 ever built, changed hands in a private sale reported at a then-record price.
A second Ferrari 250 GTO sold at RM Sotheby's Monterey auction just months after its sibling's record-setting private sale.
This 1956 DBR1, driven by legendary drivers including Carroll Shelby and Stirling Moss, remains the only Aston Martin to win the 24 Hours of Le Mans outright.
This 1956 Ferrari 290 MM was raced by five-time Formula 1 World Champion Juan Manuel Fangio before later changing hands at auction.
The five competition cars that turned checkered flags into eight-figure paydays.
This 1954 Mercedes W196, driven by Fangio to victories on his way to that season's World Championship, remains the record holder for the most expensive F1 car ever sold at auction.
This 1970 Porsche 917K, a Le Mans-winning prototype, was famously used in the filming of Steve McQueen's racing film Le Mans.
The Brawn GP team formed from the ashes of Honda's withdrawal from F1 in 2009 and won the World Championship in its only season, driven by Jenson Button.
This Ferrari F2001, driven by Michael Schumacher during his dominant championship-winning 2001 season, sold at auction.
This McLaren MP4/8, driven by Ayrton Senna during the 1993 season, sold at auction decades after his death.
The five artifacts and documents that put a price tag directly on the past.
One of the most complete Tyrannosaurus rex skeletons ever discovered sold at Christie's to a then-anonymous buyer.
This 72-page manuscript, handwritten and illustrated by Leonardo da Vinci himself, sold to Bill Gates and remains the record holder for the most expensive book ever sold.
This 1297 copy of the Magna Carta, one of only a handful ever to leave England, sold to private equity billionaire David Rubenstein.
One of only eleven surviving copies of the first book printed in British North America sold at auction, setting a record for a printed book.
One of only 26 known surviving copies of the original 1776 printing of the Declaration of Independence sold at auction.
The five ways billionaires — and a few civilians — paid their way off the planet.
Payments-processing billionaire Jared Isaacman personally funded and commanded the first orbital spaceflight crewed entirely by civilians.
Fashion billionaire Yusaku Maezawa bought out an entire SpaceX Starship flight for a private lunar flyby, inviting artists from around the world to join him for free.
Private citizens have been buying seats to the International Space Station for over two decades, starting with businessman Dennis Tito's pioneering 2001 flight.
Blue Origin auctioned off a single seat on its first-ever crewed New Shepard flight, with bidding closing at $28 million.
Virgin Galactic's suborbital spaceplane tickets, priced at $450,000 per seat, have sold to hundreds of people on a years-long waiting list.
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