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From financial ruin to jail time, here are the big billionaire downfalls that compete with Sam Bankman-Fried’s $17 billion FTX collapse. The world watched in shock last week as the floor fell out from under Sam Bankman-Fried. Over the course of just a few days, the 30-year-old founder and former CEO of cryptocurrency exchange FTX went from one of the 50 richest people in America and one of crypto’s most influential figures to the poster boy of the biggest crypto collapse to date.

A skeptical report from Coindesk about the finances of FTX’s sister company, Alameda Research, kicked off the decline. The revelation that at least $5.8 billion of Alameda’s assets were tied to FTX’s native token, FTT, caused investors to frantically withdraw their funds from the exchange. Later reports from The Wall Street Journal and others alleged that Alameda Research used as much as $10 billion of customer funds from FTX to make its bets–something that is highly illegal. Bankman-Fried essentially admitted to trading using FTX customer assets in an exchange with a Vox reporter. Bankman-Fried’s estimated fortune went from $17 billion to less than $1 billion in days. Forbes figures now it might be closer to zero. Alameda Research, FTX and FTX U.S. filed for bankruptcy on Friday, November 11, and Bankman-Fried stepped down as CEO the same day. (SBF might have hidden away some cash from a stake he reportedly sold to investors or from $2.7 billion in loans he took from Alameda Research.)

While the fallout from FTX’s implosion is still being uncovered, one thing is clear: Few other billionaires have fallen as far and as fast as Bankman-Fried. Among those who lost nearly their entire fortunes within the course of just a few days or weeks are investor Adolf Merckle, once one of Germany’s richest people who was wrecked by the 2008 financial crisis, and Kanye West, whose antisemitism proved his undoing.

Two superrich tycoons who never made the Forbes billionaires list but also had massive blowups: Bernie Madoff (d. 2021), the infamous fraudster who ran the biggest Ponzi scheme in history, and Archegos Capital Management’s Bill Hwang, whose investment firm collapsed almost overnight last year leading to an estimated $10 billion in losses for some of the world’s biggest banks.

Over the past 20 years, other fortunes have imploded for a wide variety of reasons including fraud and deceit. Many of these blowups have led to lawsuits and even jail time. That includes Elizabeth Holmes, the founder of now-defunct blood testing firm Theranos, who was sentenced on Friday to more than 11 years in prison for defrauding investors. Two others are now behind bars while one is on house arrest and another is awaiting trial.

The final page in SBF’s increasingly bizarre story has yet to be written. While the world watches to see what fate faces him and FTX, here’s a look at the biggest billionaire downfalls of recent history—and where these individuals stand today. (In descending order from most recent):

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1. Kanye West: A shoe empire toppled by antisemitism Peak net worth: $2 billion in April 2022 Net worth now: $400 million Date of blowup: October 2022 After Kanye West put forth a stream of antisemitic comments, conspiracy theories and other controversial behavior, the rapper and designer now known as Ye was dropped by Yeezy’s key business partner Adidas in October. That followed Ye’s termination the previous month of what was supposed to be a 10-year contract with clothing retailer Gap. Also cutting ties with Ye were French fashion house Balenciaga, retailer Foot Locker, his talent agency CAA and his banker JPMorgan. Despite the meltdown of his business empire, Ye is still worth an estimated $400 million from the value of his personal real estate, music catalog, cash and a 5% stake in Skims, the $3.2 billion shapewear brand started by his ex-wife, billionaire Kim Kardashian.

Jamel Toppin/The Forbes Collection

2. Rishi Shah: Accused of fraud, awaiting trial Peak net worth: $3.6 billion in 2017 Est net worth now: $0 Date of blowup: 2018 Rishi Shah turned heads as the young, college-dropout founder of buzzy healthcare media startup Outcome Health, which raised $600 million at a $5.6 billion valuation in May 2017. Within two years of Shah entering the billionaire ranks, however, he and two top executives from Outcome were charged with fraud for allegedly stealing about $1 billion from clients, lenders and investors by misrepresenting the company’s financial performance and the success of its products. The trio all pled not guilty after they were charged in 2019, and are set to stand trial in 2023.

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3. John Kapoor: Disgraced drugmaker in prison Peak net worth: $3.3 billion in 2015 Est net worth now: N/A Date of blowup: 2017 Pharma industry entrepreneur and investor John Kapoor was the founder, CEO and chairman of opioid manufacturer Insys Therapeutics. In October 2017, Kapoor was arrested and charged with conspiring to bribe doctors to prescribe the company’s fentanyl spray Subsys, which was designed to ease cancer-related pain, to patients who didn’t need it. Insys declared bankruptcy and said it was shutting down its operations in 2019. The Indian-born businessman, who dropped out of Forbes’ billionaires rankings just months after his arrest, received a five-and-a-half year prison sentence in 2020 after a jury found him and four other Insys executives guilty of a racketeering conspiracy. He’s set to be released in August 2024, according to the Federal Bureau of Prisons.

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4. Elizabeth Holmes: One-time medical mogul sentenced to 11 years in prison Peak net worth: $4.5 billion in 2015 Est net worth now: $0 Date of blowup: 2016 Theranos cofounder Elizabeth Holmes was once the toast of the tech world for developing a device she claimed would revolutionize blood testing by using just a drop or two of blood from a person’s fingertip. In 2015, the Stanford University dropout was the richest self-made woman in America. A year later, Forbes lowered our estimate of her net worth to nothing, after the technology proved to be unreliable and as the company faced a slew of investigations from federal agencies. In 2018, she was indicted for wire fraud. The case went to trial in 2021. During her trial, Holmes tried to pin the blame on her ex-boyfriend and Theranos’ former president and chief operating officer, Ramesh “Sunny” Balwani. However, jurors didn’t buy it and convicted Holmes on four charges of defrauding investors in January 2022. Pregnant with her second child, she was sentenced to more than 11 years behind bars in November 2022. Balwani was found guilty, too, and faces up to 20 years in prison for wire fraud and conspiracy to commit wire fraud.

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5. Eike Batista: Once Brazil’s richest sentenced to 30 years Peak net worth: $30 billion in 2012 Est net worth now: N/A Date of blowup: 2013 A man with outsized ambition, Brazilian oil and gas entrepreneur Eike Batista once pledged to Forbes he would become the world’s richest person (a title that has since gone to Tesla CEO Elon Musk). For a while, it seemed possible. In early 2012, Batista was worth an estimated $30 billion as the prices of his publicly traded energy companies, housed under the parent company EBX Group, soared. But within a year, amid failures to meet production and financial targets, his energy empire began to crumble. It became clear that his flagship oil company OGX had vastly overstated its oil reserves. OGX filed for bankruptcy in 2013 after defaulting on a $45 billion bond payment, marking the largest corporate default in Latin American history. Batista was sentenced to 30 years in prison in 2018 for bribing the now-imprisoned former Rio de Janeiro Governor Sergei Cabral $16.5 million in exchange for state contracts. He is reportedly living in his mansion under house arrest.

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6. Vijay Mallya: Good times gone bad Peak net worth: $1.6 billion in 2007 Est net worth now: N/A Date of blowup: 2012 Known as “the King of Good Times” for his flamboyant lifestyle, Mallya ran United Spirits, one of India’s largest liquor companies, and the now-defunct Kingfisher Airlines. After entering the aviation space in 2005, the liquor mogul racked up debts of more than $1 billion owed to numerous Indian banks as he sought to keep his struggling Kingfisher Airlines afloat. At one point the second largest domestic carrier in India, Kingfisher became insolvent and shut down in 2012; pilots and cabin staff were unpaid for months on end while Mallya continued to throw extravagant parties, Forbes reported at the time. Mallya fled to the U.K. in 2016 after defaulting on debts to lenders by State Bank of India and is believed to still be living there today; he is the subject of an extradition effort. Mallya was declared bankrupt by a British court last July, paving the way for Indian banks to seek repayments of Mallya’s outstanding debts.

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7. Anil Ambani: Black sheep of billionaire family Peak net worth: $45 billion in 2007 Net worth now: N/A Date of blowup: 2010-2020 Anil Ambani and his older brother Mukesh Ambani inherited India’s biggest fortune from their late father Dhirubhai Ambani (d.2002). An ugly battle for control of the company led to a split between the brothers. Mukesh is now Asia’s second richest person, and Anil is near financial ruin, resulting from failed deals and mounting debts. His business’ collapse led to years of legal disputes linked to lenders across India and China, who are still trying to recover funds from the younger Ambani. His Reliance Group finally entered bankruptcy proceedings in 2019, by which point it had lost more than 90% of its value. Despite a historically contentious relationship, his brother Mukesh at one point helped pay off some of his debt to Swedish telecom company Ericsson when Anil was facing prison for nonpayment. The remains of his empire are being slowly seized and sold.

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8. Allen Stanford: The Ponzi prince Peak net worth: $2.2 billion in 2008 Est net worth now: $0 Date of blowup: 2009 A fraudster who gave Bernie Madoff a run for his money, Stanford was convicted in 2012 for running a $7 billion Ponzi scheme through his Stanford Financial Group, an offshore bank based in Antigua. The former billionaire made a killing for about two decades by selling fraudulent high-yielding certificates of deposit and then using the funds for dubious investments and to fund his lavish lifestyle, according to prosecutors. In 2012, he was sentenced to 110 years in prison, which he is currently serving in a high-security prison in Coleman, Florida. The victims of Stanford’s scheme have had their money returned at a slower rate than Madoff’s victims. Just over $1 billion has been recovered to date. In January 2022, a Texas judge ruled that five banks sued for $4 billion by a group of Stanford investors for allegedly facilitating the fraudster by providing him financial services would have to stand trial. The banks have denied the claims and unsuccessfully tried to dismiss the lawsuit.

(GERMANY OUT) Merckle, Adolf – Entrepreneur, Germany (Photo by Brinckmann/ullstein bild via Getty Images)

ullstein bild via Getty Images 9. Adolf Merckle: A financial crisis casualty Peak net worth: $12.8 billion in 2007 Est net worth now: N/A Date of blowup: 2008 Merckle was a German industrialist whose investment outfit got hit badly in the financial crisis of 2008. Making matters much worse was a big bet he made against Volkswagen AG, which backfired in October that year when it was revealed European car giant Porsche was vying to take over the company, sending Volkswagen’s share price soaring. Merckle sought more than $1 billion in bridge loans to cover the losses incurred by his VEM Vermoegensverwaltung conglomerate, which by that point was heavily leveraged. As his empire teetered toward collapse, Merckle took his own life by stepping in front of a train near his home in Blaubeuren, Germany in 2009. After Adolf’s death, his son Ludwig turned around the tumbling family fortune, selling off pieces but eventually recovering. He is now worth more than $5 billion.

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10. Mikhail Khodorkovsky: Putin-induced collapse of Russia’s richest man. Peak net worth: $15 billion in 2004 Est net worth now: N/A Date of blowup: 2006 The former head of Russian oil and gas giant Yukos, Khodorkovsky was once Russia’s richest man, worth an estimated $15 billion at the height of his wealth in 2004. But after a public sparring with Putin over government corruption, Khodorkovsky was arrested and jailed for tax evasion, embezzlement and fraud, allegations he has denied and blasted as politically motivated. Yukos, once Russia’s largest oil company, was broken apart and declared bankrupt in 2006; most of its assets were absorbed by the state-controlled oil company Rosneft. Khodorkovsky was pardoned in 2013 and has since relocated to London, where he remains a vocal critic of Putin. “The world will not be a safe place as long as Putin remains in power,” the former billionaire said in May at the Milken Institute’s annual conference.

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