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.
The Stroh Brewing Company was founded in Detroit in 1850 by Bernhard Stroh, a German immigrant, and grew over five generations into one of the largest brewers in the United States — and one of the largest private family fortunes the country had ever produced. At its 1980s peak the family was worth at least $700 million by Forbes’s reckoning, with the family name on the Forbes 400 and Stroh’s the third-largest brewing empire in America, behind only Anheuser-Busch and Miller.
Then, in the space of roughly two decades, it all came apart. A debt-fueled gamble to go national — above all the 1982 takeover of the failing Joseph Schlitz Brewing Company, financed with hundreds of millions in borrowed money — left the company saddled with debt just as the industry consolidated around two giants. Stroh’s missed the light-beer wave, lost market share year after year, and could never out-earn its interest payments.
By February 1999 the family was selling the 149-year-old brewery for parts, its brands divided between Pabst and Miller. The proceeds went largely to debt and pension obligations; what trickled to the family through trusts ran out within a few years. Forbes later estimated that, had the family simply sold the business at its peak and invested in the S&P 500, the fortune could have been worth roughly $9 billion by 2014. Instead it was essentially gone.
The Stroh story has become a textbook case of generational wealth destruction — the old proverb of “shirtsleeves to shirtsleeves in three generations,” here stretched across five or six. It was not a swindle or a market crash but a slow, self-inflicted unwinding: a strategic bet too big for the balance sheet, made in a brutally consolidating industry, by a family that gambled a profitable status quo on becoming a national champion and lost.