20 Millionaires Who Blew Fortunes On Bizarre Obsessions

Sarah Winchester was the wife of William Wirt Winchester, heir to the Winchester rifle wealth. Following the deaths of both her husband and baby daughter, she embraced spiritualism and purchased a farmhouse in San Jose, California, where she kept carpenters working around the clock for the remaining years of her life. It is said that a medium warned her that construction must never stop. At the time of her passing, the mansion contained approximately 160 rooms, including staircases that terminated in ceilings and doors opening onto blank walls. It cost about $5.5 million to build.

The oil-tool heir Howard Hughes Jr. was an accomplished pilot and Hollywood producer. He invested over $23 million in the 1940s in a giant flying boat, the H-4 Hercules, with a wingspan longer than a football field. It was intended to carry troops across the Atlantic during the Second World War and was built of laminated birch because metal was in short supply. It flew exactly once, lifting off and covering less than a mile before coming back down. Years later, he retired to an isolated suite at a Las Vegas hotel. He bought the hotel outright after the owners tried to evict him from his suite.

William Randolph Hearst inherited and grew a newspaper empire, and from 1919, he began building a massive estate called San Simeon on a Californian hilltop. He bought out whole Spanish monasteries and shipped back whole medieval ceilings, tapestries, and sculptures in crates. When he finished the castle, it had 115 rooms and was home to the world’s largest private zoo. His spending of about $10 million helped push his media company into court-ordered debt restructuring in 1937. After that, trustees gave him a fixed allowance.

In 1864, Ludwig II succeeded to the Bavarian throne. An ardent Romantic, he became infatuated with Germanic mythology and grand opera. Instead of spending state funds, he used his royal private purse and borrowed heavily from overseas bankers to construct his dream castles: Neuschwanstein, Herrenchiemsee and Linderhof. His personal debt ballooned to 14 million marks, leading ministers to have him declared incompetent in June 1886 and deposed. Days later, he was found dead in a lake, though the circumstances remain a matter of scholarly debate.

Harry Kendall Thaw got his money from a Pittsburgh coal and railroad fortune and received an enormous annual income. He became obsessed with the architect Stanford White, who had courted Evelyn Nesbit, a chorus girl who later became Thaw’s wife. At Madison Square Garden, Thaw shot White dead. Thaw’s mother paid more than $1 million for top attorneys and medical experts, who won an insanity verdict. He was sent to an asylum, escaped from it twice, was later pronounced sane, and went free for decades.

A wealthy Welsh surgeon and landowner named Dr. William Price declared himself a High Druid, dressed in a green suit topped by a fox skin, and erected a round temple at Llantrisant. He was brought to court after attempting to cremate his dead infant son atop a local hill. An autopsy revealed that the boy had died from natural convulsions, so the real question for the court was whether or not cremation itself was legal. Price paid for his own lawyers and ultimately won his case and set a precedent that cremation was not illegal under British law.

The 5th Marquess of Anglesey, Henry Cyril Paget, inherited a sprawling British estate upon coming of age. He converted the family chapel into a theater and performed his own dances wearing expensive silk robes and diamond tiaras. He also rigged the cars he owned to spray perfume out of their exhaust pipes. Within a few years, he’d racked up enough debt to be declared bankrupt and watched his costumes get sold off at auction. He died broke shortly thereafter, in his 20s.

Dr. John Harvey Kellogg ran the Battle Creek Sanitarium in Michigan, where he treated rich clients with a regimen of pure food and healthy living. He put a great deal of money into producing bland cereal from grains and into physical treatments like vibrating chairs, hydrotherapy, where patients were kept under running water for hours, and yogurt enemas. He believed, based on his religious views, that digestive health and sexual urges were closely linked. While testing one of his diets, he accidentally patented flaked corn cereal alongside his brother, Will Keith Kellogg, who later built the cereal company on his own.

The 5th Duke of Portland, William Cavendish-Scott-Bentinck, was one of the wealthiest landowners in Britain. But he also suffered from social anxiety. Over the course of 20 years or so, he commissioned hundreds of men to excavate about two and a half miles of tunnels beneath his sprawling country seat, Welbeck Abbey. Among these were an underground library and a gas-lit carriage tunnel stretching over a mile. And yet despite the scale of the project, the duke dealt with the men only via notes slipped under doors.

Carlos de Beistegui was a Franco-Mexican collector of art, heir to a silver and real estate empire. He commissioned the architect Le Corbusier to build him a surrealistic penthouse apartment in Paris that contained moving hedge walls and a periscope so he could survey the city below. It was later torn down. Later, he spent millions to throw Le Bal du Siècle in his palatial Venetian home, walking through a sea of 1,500 costumed partygoers in 16-inch platform shoes.

Timothy Dexter was a self-styled “Lord” and a Newburyport, Massachusetts, merchant who amassed his fortune by purchasing depreciated wartime currency at a discount and waiting until the bills had appreciated beyond belief before cashing in. After rivals suggested it as a joke meant to ruin him, Dexter shipped bed-warming pans to the West Indies, and plantation owners bought them anyway. They used them as ladles for molasses. Dexter erected dozens of wooden statues of prominent people, including himself, in and around his estate. And later, he published a book that contained no punctuation.

Edward James, the British poet who had inherited an American railroad fortune and who patronized Surrealist artists like Salvador Dalí, came to Mexico and found that his precious orchids had been destroyed by frost. Rather than lose them again, James would build flowers out of concrete, flowers that would never die. He spent millions over the next few decades on 80 acres of concrete staircases, Gothic arches, and sculpted blossoms, deep in the rainforest near the town of Xilitla. He worked with a local builder, Plutarco Gastélum, using no formal blueprints.

George Whittell Jr. inherited a San Francisco banking and real estate fortune. He was selling off a massive block of shares just before the 1929 market crash, preserving the fortune he would later spend on Lake Tahoe. In the mid-1930s, he purchased 27 miles of Lake Tahoe shoreline in Nevada and constructed Thunderbird Lodge. It had a long tunnel that stretched underground and a cardhouse on the lake for high-rolling poker games. Whittell also had a pet lion named Bill that rode in his car. An elephant, added to his menagerie, came to him one summer, but the cold weather drove it away after a few months.

Thomas W. Lawson was a wealthy copper-stock speculator known for his extravagant spending. He spent millions building a mansion called Dreamwold in Scituate, Massachusetts. He paid for the 153-foot Lawson Tower in Scituate, which was basically a giant wooden shell containing a ten-bell chime, to disguise a hideous municipal water tank. He financed the only seven-masted schooner ever built. It went down off England on a Friday the 13th, the same title he used for one of his novels.

John “Mad Jack” Mytton inherited an estate in Shropshire that paid him a fortune each year. He maintained thousands of hunting hounds and dozens of horses, purchased a parliamentary seat, which he attended for half an hour, rode a tamed bear into his dining room, and once set fire to his nightshirt in a failed attempt to cure his hiccups. A contemporary biographer recorded these feats in his memoirs of Mytton’s life. The costs of his extravagance depleted his family’s wealth and ended with him dying in a debtor’s prison at a young age.

Fonthill Abbey was built for William Beckford, the richest commoner in England, who was an English novelist and sugar-plantation heir. It sits on a Wiltshire estate funded by his enormous private income. Beckford paid the architect James Wyatt to build the tower, which is 300 feet high and in the Gothic style. He had crews working day and night without proper foundations. The tower collapsed in a storm and was rebuilt. Beckford later sold the abbey to pay off debts, and the tower’s final collapse came after he had already moved on.

Henry Ford, founder of the Ford Motor Company, built a fortune worth hundreds of billions in today’s money. In pursuit of a reliable source of rubber, he purchased millions of acres near the Tapajos River in Brazil to construct a settlement known as Fordlandia. He invested over $20 million in paving roads and building homes in the style of the American Midwest, and forbade alcohol, tobacco, and any food besides a strictly American menu for his employees. Leaf blight destroyed the rubber plantations, workers rebelled against the regulations, and Ford ultimately sold the desolate settlement back to Brazil at a fraction of the cost, without ever visiting.

James Gordon Bennett Jr. inherited the New York Herald from his father and was one of the richest media men in the country. Bennett paid for the explorer Henry Morton Stanley’s expedition across Africa in order to locate the missionary David Livingstone because he wanted the scoop. At one point, he became irritated at having a bulge of money in his pocket, pulled the bills from his pants, and tossed them in a fireplace. According to a Gilded Age legend, he also once purchased a restaurant outright because it had failed to reserve his table. It’s probably from Bennett that the Brits got their exclamation, “Gordon Bennett.”

Florence Foster Jenkins had a huge inheritance from her father, a wealthy Pennsylvania lawyer and banker. She truly thought she was an excellent singer, even though she lacked pitch or rhythm. She started New York’s Verdi Club and spent big money on private recitals, vanity recordings, and flamboyant stage wear. At age 76, she rented out Carnegie Hall for a public performance, and all 3,000 tickets were gone in minutes. She had a heart attack and died a few weeks later.

Edward “Ned” Green was the son of Gilded Age miser Hetty Green, who made her fortune by refusing to spend any of it. Upon her death, Ned inherited $100 million and spent the rest of his life doing the exact opposite. He purchased the only known sheet of 100 “Inverted Jenny” airmail stamps and acquired all five known 1913 Liberty Head nickels. He also encased a 19th-century whaling ship in concrete and constructed a private airfield and radio laboratory on his estate.

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