Barbara Hutton inherited a Woolworth five-and-dime fortune as a child — by some estimates around $50 million at the depth of the Great Depression, when that sum was almost unimaginable — and spent the next five decades giving it away to husbands, hangers-on, jewelers, and hotels. When she died in 1979 at the age of 66, she is widely reported to have had only a few thousand dollars left.
The press named her the ‘Poor Little Rich Girl’ when she was still a teenager, and the cruel paradox stuck because it was true: Hutton had everything money could buy and almost nothing it could not. Her mother died when she was four (likely a suicide); her father, the stockbroker Franklyn Hutton, was distant and exploitative of her trust. She grew up fabulously rich and profoundly alone, and she spent her life trying to purchase the affection that had been missing from the start.
She married seven times, almost always disastrously and almost always expensively. Several husbands were titled Europeans who left the marriage richer than they entered it; one, the actor Cary Grant — the only husband who reportedly took none of her money and whom the papers dubbed ‘Cash and Cary’ in unfair anticipation — was the exception that proved the rule. Each divorce cost her a settlement; each marriage cost her more.
Hutton is the defining case of the heir’s ruin: a fortune large enough to last many lifetimes, dissolved in a single one through a combination of grief, generosity, exploitation, and the simple fact that a great deal of money spent steadily for fifty years on the most expensive things in the world will eventually run out.
When Cornelius “Commodore” Vanderbilt died on January 4, 1877, he left the largest fortune anyone in America had ever assembled — roughly $100 million, a sum so vast it was said to exceed the cash then held in the entire United States Treasury. Built first on steamships and then on the consolidation of the New York Central and Hudson River railroads, it was the foundation of what looked like an unassailable dynasty. The Commodore, distrustful of his children’s competence, left about 95 percent of it — some $95 million — to a single son, William Henry Vanderbilt, in the deliberate belief that concentrating the capital would preserve it.
For one more generation, the strategy worked spectacularly. William Henry roughly doubled the fortune, to an estimated $194–200 million by the time of his own death in December 1885, briefly making him the richest man in the world and the only heir ever to increase the Vanderbilt fortune. But he broke from his father’s logic and divided the money widely among his eight children — and that third generation, raised to spend rather than to build, set about converting the greatest cash fortune in America into marble, art, yachts, and social rank.
The Vanderbilts of the Gilded Age built more grand houses than any family in American history: a row of palaces on Fifth Avenue, “The Breakers” and “Marble House” at Newport, the 250-room Biltmore in North Carolina — still the largest private home in the country. None of it generated income; all of it consumed capital, demanded armies of servants, and locked the family into a ruinous competition for social supremacy. The fortune was steadily spread thinner across more heirs and poured into assets that only ever cost money to keep.
Within about thirty years of the Commodore’s death no Vanderbilt was among the richest Americans, and the Fifth Avenue mansions were eventually torn down for commercial real estate. In his 1989 history Fortune’s Children: The Fall of the House of Vanderbilt, family member Arthur T. Vanderbilt II recorded that when 120 members of the family gathered for a reunion at Vanderbilt University in 1973, not one of them was a millionaire. It remains the textbook case of a dynasty that spent, rather than grew, what it inherited — the mirror image of Cornelius Vanderbilt’s self-made rise chronicled on our sister site, Up From Nothing.
William Frederick “Buffalo Bill” Cody was, for a stretch of the late nineteenth century, plausibly the most famous human being on earth — a frontier scout turned showman who packaged the American West into a touring spectacle and sold it to millions of people across the United States and Europe. Buffalo Bill’s Wild West, founded in 1883, earned him several fortunes over three decades. He spent or lost every one of them, and died in 1917 effectively broke, his great show foreclosed and auctioned out from under him.
Cody made money the way few entertainers ever have, and he gave it away and gambled it away with equal abandon. He was famously, almost compulsively generous, handing cash to old friends, broke cowboys, and anyone with a hard-luck story. He was also a serial sucker for investment schemes wholly outside his expertise: an Arizona gold-and-tungsten mine that swallowed money for years, irrigation and land-development ventures in Wyoming, a hotel, ranches. The show kept refilling the well, and the schemes and the generosity kept draining it faster.
The two enterprises that defined his decline were a mine and a loan. The Campo Bonito mine near Oracle, Arizona, which he organized into a $600,000 company around 1910, never came close to paying back what he sank into it. And in January 1913, short of cash to keep his combined “Two Bills” show afloat, Cody borrowed twenty thousand dollars from Harry Tammen, a Denver Post owner and circus operator — a loan that, when Cody fell behind, gave Tammen the lever to seize and auction the entire Wild West show that July.
For his last years the most famous showman in the world was, in effect, an employee — performing for the very circus interests that had taken his show, unable to retire because he could not afford to. He died in Denver on January 10, 1917. By the most cited accounts his once-enormous earnings had dwindled to under a hundred thousand dollars in assets, much of it encumbered. Buffalo Bill is the classic case of the great earner undone not by a single crash but by a lifetime of bad bets and open-handedness that no income could outrun.
Evalyn Walsh McLean was the last private owner of the Hope Diamond, the most famous and most fabled “cursed” gem in the world, and one of the great spenders of the American Gilded Age. The daughter of a poor Irish immigrant who struck it rich with a Colorado gold mine, she married into the family that owned The Washington Post, and for a time she commanded a fortune that let her treat money as something that simply appeared.
In January 1911 her husband bought the Hope Diamond from the Paris jeweler Pierre Cartier for $180,000, and Evalyn wore the 45-carat blue stone to parties as a casual ornament — even, by her own telling, letting her great dane wear it. She delighted in its reputation as a bringer of doom, but her own life would deliver tragedy after tragedy: the death of her young son, the disintegration of her marriage, the loss of her daughter, and the steady erosion of the wealth that had once seemed inexhaustible.
McLean’s spending was legendary and ceaseless, and the family’s income could not keep pace. Her husband, Edward “Ned” McLean, drank himself into mental collapse, lost control of the Post, and was eventually declared legally insane. In one of the most notorious episodes of her life, she was swindled out of more than $100,000 by the con man Gaston Means, who claimed he could recover the kidnapped Lindbergh baby through underworld contacts.
By the time she died in 1947, the great Walsh-McLean fortune had largely dissolved into debt, and her jewels — including the Hope Diamond — were sold to settle her estate. The diamond passed to the jeweler Harry Winston and, in 1958, was donated to the Smithsonian Institution, where it remains. Evalyn Walsh McLean’s life stands as a parable of inherited wealth spent faster than it could ever be replaced.
Ludwig II came to the throne of Bavaria in 1864 at the age of eighteen, a strikingly handsome and intensely romantic young man with little taste for the duties of state and a consuming passion for art, music, and architecture. Over the next two decades he poured his wealth into two enthusiasms above all others: the operas of Richard Wagner, whom he rescued from his creditors and bankrolled for years, and a series of extravagant fantasy palaces — Neuschwanstein, Linderhof, and Herrenchiemsee — built to satisfy a private vision of medieval and Bourbon splendor rather than any public need.
Crucially, Ludwig financed these projects not from the Bavarian state treasury but from his own civil list — the personal income granted to the crown — and, when that ran out, from a mounting pile of personal loans. By the mid-1880s his debts had reached roughly 14 million marks, an enormous sum, and he was demanding that his ministers raise still more, threatening to dismiss the entire government when they balked. The building never stopped; Linderhof was completed, Neuschwanstein and Herrenchiemsee remained unfinished, and the king’s appetite for new and grander schemes showed no sign of slowing.
Unable to control the king’s spending or to extract more credit, Ludwig’s ministers moved against him in June 1886. They assembled a medical commission, headed by the psychiatrist Dr. Bernhard von Gudden, which declared Ludwig insane — paranoid and unfit to rule — without, by most accounts, ever personally examining him. On that basis he was deposed and placed under custody at Berg Castle on the shore of Lake Starnberg.
Three days later, on the evening of June 13, 1886, Ludwig and Dr. von Gudden went for a walk along the lake and never returned. Both were found dead in the shallow water hours later, in circumstances that have never been satisfactorily explained and remain disputed to this day — officially ruled a drowning, variously suspected to have been suicide, an escape attempt gone wrong, or even murder. The castles that ruined and arguably killed him became, within a generation, among the most visited and most profitable tourist attractions in Germany.
Michael Jackson was one of the highest-earning entertainers who ever lived, generating an estimated $1 billion or more across his career and, from 1985, owning one of the most valuable assets in popular music: the ATV catalog containing most of the Beatles’ songs. Yet by the time he died on June 25, 2009, at age 50, he was reported to be roughly $400 million to $500 million in debt, his finances hollowed out by decades of spending that vastly outran even his colossal income.
Jackson’s earnings in his peak years — reportedly $50 million to $100 million annually from the mid-1980s to mid-1990s — were matched by an extraordinary outflow: Neverland Ranch and its private amusement park, art, antiques, jewelry, and a lifestyle estimated at tens of millions of dollars a year. To sustain it he borrowed heavily, most consequentially a roughly $270 million loan secured against his music-publishing assets, and by the end he was said to be accruing debt faster than even his catalog could service it.
What makes Jackson nearly unique in this catalogue is what happened next: the ruin reversed after his death. His estate, run by executors John Branca and John McClain, sat atop assets — above all his 50% stake in Sony/ATV Music Publishing — that proved far more valuable than the debt. The “This Is It” documentary, Cirque du Soleil shows, reissues, and a series of landmark catalog sales generated billions, retired every dollar of debt, and turned a deeply insolvent estate into one of the most profitable in entertainment history.
This entry concerns only the financial story. The 1993 and 2005 child-abuse matters are noted strictly as documented public-record events with financial consequences — a reported civil settlement in 1993 and a full criminal acquittal in 2005 — and not relitigated here.