Even celebrities make bad investments. Here are 20 times their financial gambles went terribly wrong. So, if you’ve made some mistakes, you’re not alone.
#1. Kim Basinger’s Town Purchase
Kim Basinger bought the town of Braselton, Georgia, for a staggering $20 million, aiming to turn it into a film production hub. She sold it for a mere $1 million, swallowing a massive $19 million loss.
#2. Bono’s Tech Misfire
Bono invested in Palm through his investment company just before smartphones dominated the market. The company’s value plummeted, and Bono’s stake lost nearly 50% of its worth.
#3. Kevin Bacon’s Ponzi Scheme Loss
Kevin Bacon and Kyra Sedgwick were among the high-profile victims of Bernie Madoff’s massive Ponzi scheme, losing millions in what they thought was a safe investment.
#4. Nicolas Cage’s Real Estate Disaster
Nicolas Cage’s investment in multiple luxury properties backfired during the 2008 financial crisis, forcing him to sell many at a loss due to foreclosure threats.
#5. Johnny Depp’s Expensive Island
Johnny Depp spent millions on a private island in the Bahamas but didn’t account for the hefty maintenance and staff costs, which contributed to his financial issues.
#6. Chris Tucker’s Real Estate Collapse
Chris Tucker faced foreclosure on at least one of his properties and had a run-in with the IRS over $11 million in back taxes, thanks to high-risk real estate investments.
#7. Evander Holyfield’s Financial Knockout
Evander Holyfield earned over $230 million during his career but filed for bankruptcy due to poor investment choices and lavish personal spending.
#8. Brendan Fraser’s Film Flops
Brendan Fraser invested in several film projects that never saw the light of day, contributing to financial strains exacerbated by personal expenses.
#9. Michael Vick’s Illegal Venture
NFL star Michael Vick invested in an illegal dog fighting ring, costing him a $130 million contract and a 21-month prison sentence.
#10. Wesley Snipes’ Tax Scandal
Wesley Snipes was convicted of failing to pay $7 million in taxes after following dubious financial advice, leading to a three-year prison stint.
#11. Curt Schilling’s Video Game Failure
Curt Schilling invested $50 million into his video game company, 38 Studios, only to see it collapse, leaving him and his employees stranded financially.
#12. Heidi Montag’s Pop Star Dreams
Heidi Montag spent over $2 million on a pop album that flopped, selling fewer than 1,000 copies in its first week.
#13. MC Hammer’s Fast Money Drain
MC Hammer went through $30 million, filing for bankruptcy in 1996 because his lavish lifestyle far outstripped his rap earnings.
#14. T-Pain’s App Mishaps
T-Pain lost $500,000 on a startup app venture that failed to catch on, showing that not every celebrity touch turns to tech gold.
#15. Drew Barrymore’s Wine Wobble
Drew Barrymore’s wine brand, Barrymore Wines, struggled to compete in the crowded luxury wine market, facing mixed reviews and modest sales.
#16. Donald Trump’s Casino Bankruptcies
Donald Trump’s casino ventures in Atlantic City, including the Taj Mahal, went bankrupt, totaling combined debts of $1.2 billion.
#17. Kanye West’s Fashion Flop
Before his Yeezy success, Kanye West poured $30 million into a high-fashion line that crashed before it could even take off, nearly bankrupting him.
#18. Larry King’s Bagel Bust
Larry King attempted to revolutionize the bagel world with Bagel Bakers, but the company folded after a few years, proving even icons can misjudge the market.
#19. Ja Rule’s Fyre Festival Fiasco
Ja Rule faced multiple lawsuits after the disastrous Fyre Festival, which promised luxury and delivered chaos, tarnishing his reputation and finances.
#20. Steven Spielberg’s Sinking Restaurant
Steven Spielberg’s restaurant venture, Dive!, submerged under its high concept theme, closing its doors after failing to attract a steady crowd.
Before You Judge Your Own Flops…
Seeing these colossal missteps might make your own investment blunders seem a bit less daunting. Take it as a learning experience—every loss is just a step towards a smarter investment.
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Featured Image Credit: Shutterstock / Andrea Raffin.
The content of this article is for informational purposes only and does not constitute or replace professional financial advice.
For transparency, this content was partly developed with AI assistance and carefully curated by an experienced editor to be informative and ensure accuracy.