Buffalo Bill Cody — the Showman Who Made and Lost Several Fortunes

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.

Michael Jackson — the King of Pop Who Died Half a Billion in Debt

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.