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Mike Tyson -

Mike Tyson, the once-undisputed heavyweight boxing champion of the world, fell into crippling debt that cost him many millions. Tyson finally was forced to file for bankruptcy in 2003.

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Elizabeth Holmes -

The infamous progenitor of the Theranos start-up scam was once one of the fastest rising stars in finance. That all came crashing down when it was revealed that her revolutionary start-up was actually a scam. Ultimately, Holmes was sentenced to more than 11 years in prison.

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Donald Trump -

President Elect Donald Trump is renowned for his real estate empire. He is also a bankruptcy champion, one could say. He has faced multiple business setbacks, including the bankruptcies of his Atlantic City casinos. Although he managed to rebound, these financial hurdles left a big dent on his business legacy.

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Sam Bankman-Fried -

In March 2024, Sam Bankman-Fried, the fallen “Crypto King,” was sentenced to 25 years in prison for defrauding customers and investors. The prosecution accused him of funneling billions from FTX into his other company, Alameda Research. The 31-year-old was the founder of FTX, a cryptocurrency exchange company created in 2019 that became a multi-billion-dollar empire, but crumbled within three years. It’s estimated that his net worth went from US$26 billion to zero within a matter of months.

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Wesley Snipes -

The actor was faced with legal trouble for tax evasion, which resulted in a prison sentence. The financial repercussions, including hefty fines and legal fees, took a substantial toll on his once-impressive wealth.

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Bernie Madoff -

Infamous fraudster Bernie Madoff stole billions through the largest Ponzi scheme in history. After amassing over US$60 billion over the course of 11 years, Madoff was caught, charged, and sentenced to no less than 150 years in prison.

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Allen Stanford -

Bernie Madoff ran the largest Ponzi scheme in history, and Allen Stanford ran the second largest. Stanford's 18,000 duped investors lost a grand total of US$7 billion. In 2012, Stanford was charged and convicted on 13 counts of fraud, and is currently serving a 110-year prison sentence, with a net worth of exactly US$0.

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Nicolas Cage -

Famous for his eclectic film roles, Nicolas Cage went on a spending spree that included buying castles, rare artifacts, and a dinosaur skull. His extravagant purchases and financial mismanagement led to legal troubles and significant debt.

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Mark Twain -

Celebrated writer Mark Twain invested heavily in a typesetting machine, believing it would revolutionize publishing. Unfortunately, the machine failed, and Twain faced severe financial difficulties during his later years.

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Michael Jackson -

Despite his unparalleled musical talent and success, Michael Jackson's extravagant lifestyle and a series of legal battles drained his fortune. Spending over US$500 million on cars, houses, and a zoo left him in a precarious financial situation at the time of his death.

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Curt Schilling -

The former baseball star's post-retirement venture into the video game industry turned into a disaster. His company, 38 Studios, declared bankruptcy after failing to produce a successful game, resulting in significant financial losses.

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Martha Stewart -

Domestic diva Martha Stewart infamously faced legal troubles, including insider trading charges, which had a significant impact on her media empire and personal finances. She served five months in prison, at Alderson Federal Prison Camp in West Virginia.

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Johnny Depp -

Known for his iconic roles in Hollywood, Johnny Depp found himself embroiled in a bitter legal battle with his former management team. Combined with lavish spending habits, which include a private island and a French castle, this lawsuit took a toll on his finances. Despite earning millions per film, the actor faced dire financial straits and sold off valuable assets.

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Michael Vick -

Former NFL quarterback Michael Vick's involvement in a notorious dogfighting scandal led to his imprisonment and the loss of tens of millions of dollars in endorsements and salary. His once-soaring career was marred by this shocking fall from grace.

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50 Cent -

The rapper and entrepreneur filed for bankruptcy in 2015. It all happened several days after a court ordered him to pay US$7 million to Lastonia Leviston for posting a sex tape online without her consent. The alleged revenge post was just the tip of the debt and lawsuits thread. Despite his financial woes, however, 50 Cent managed to reorganize his finances and return to the music industry.

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Floyd Mayweather -

Boxing star Floyd Mayweather may have earned millions in the ring, but his penchant for extravagant spending and high-stakes gambling have often left him on the brink of financial instability.

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Larry King -

The legendary talk show host went through a series of divorces and made questionable financial decisions, ultimately leading to his bankruptcy filing in the late 1970s.

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Aubrey McClendon -

Chesapeake Energy, co-founded by Aubrey McClendon, was worth US$1.2 billion. But McClendon eventually found himself wrapped up in charges of fraud after it was discovered he manipulated bids for drilling rights. McClendon died in a car accident just after filing for bankruptcy.

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Jocelyn Wildenstein -

Socialite Jocelyn Wildenstein famously received more than US$2 billion in her divorce from art dealer Alec Wildenstein. As famous for her spending habits as she was for her cosmetic surgery procedures, Wildenstein could reportedly drop $1 million in a single shopping spree. This excessive spending eventually led to Wildenstein filing for bankruptcy in 2018.

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Vijay Mallya -

Liquor and airline baron Vijay Mallya was once one of the most famous men in India, known for his extravagant lifestyle. But after racking up a considerable amount of debt, Mallya was accused of bank fraud and was forced to file for bankruptcy.

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Eike Batista -

Brazilian businessman Eike Batista was once the seventh richest person in the world, thanks to his oil company OGX. Unfortunately for Batista, his business wasn't managed very well, and eventually began hemorrhaging money. Batista fell from a net worth of US$30 billion to filing for bankruptcy in 2012.

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Sean Quinn -

Once known as the richest man in Ireland, business magnate Sean Quinn's bad business dealings and unpaid debts forced him to file for bankruptcy in 2012.

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Björgólfur Guðmundsson -

Icelandic banker Björgólfur Guðmundsson singlehandedly dealt intense damage to the Icelandic economy through his shady business dealings. Guðmundsson eventually fell into debt and went bankrupt in 2008.

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Adolf Merckle -

German businessman Adolf Merckle once had a net worth of over US$9 billion, but a string of bad investments caused him to lose everything. Just when he would have been forced to file for bankruptcy, Merckle took his own life in 2009.

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Patricia Kluge -

The former wife of media mogul John Kluge once indulged in an extravagant wine-making venture in Virginia. With a vineyard estate that boasted opulent wine cellars and Tuscan-inspired villas, she spared no expense. However, her dream project crumbled when the global financial crisis hit, and the real estate market tanked. By 2011, Patricia Kluge was forced to file for bankruptcy, and her once-magnificent estate was sold at auction.

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Bernie Ebbers -

The former CEO of WorldCom was once heralded as a telecom titan. However, his legacy took a dark turn when it was revealed that he had masterminded one of the largest corporate accounting scandals in history. In 2005, he was convicted of fraud and conspiracy, sentenced to 25 years in prison, and became a symbol of corporate greed gone awry.

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Bill Hwang -

His Archegos Capital Management firm was a financial behemoth until it imploded in 2021. Hwang's massive use of leverage in risky bets on stocks led to billions in losses for his firm and a tarnished reputation in the investment world. Bill Hwang and CFO Patrick Halligan were arrested and charged with 11 criminal counts, including racketeering conspiracy and securities fraud.

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James Altucher -

Former hedge fund manager James Altucher experienced a spectacular fall from grace, going from a net worth of over US$15 million to bankruptcy. Ill-fated investments and unsuccessful business ventures were the main reasons for his financial woes.

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Chuck Feeney -

Unlike the others on this list, the "James Bond of Philanthropy" and co-founder of Duty-Free Shoppers had a hidden philanthropic agenda. Chuck Feeney secretly donated his vast fortune to charitable causes, leaving himself with US$2 million to live on. His story is a unique one, demonstrating that not all rich individuals lose their wealth due to financial recklessness.

Sources: (Bloomberg) (The Guardian)

See also: Your guide to hosting a memorable charity event

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