Fortune: $2.2 Billion
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Allen Stanford sure enjoyed the trappings of his $2.2 billion (£1.7bn) fortune, indulging in private planes and yachts during his heydays as an American financier and sponsor of professional sports.
But in 2009 it was unveiled that his wealth was acquired through ill-gotten gains via the second-largest Ponzi scheme in history, according to CNBC.
He’s now penniless and behind bars after being sentenced to a 100-year jail term in 2012.
Fortune: $1.2 billion
Indicted on charges of conspiring to rig bids for oil and gas leases
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In 2011, Aubrey McClendon was worth $1.2 billion (£934m) as the co-founder of Chesapeake Energy, a pioneer in the use of new technology in the oil and natural gas industry.
But five years later, he was named by Forbes as “America’s Most Reckless Billionaire”, losing his billions when he was indicted on charges of conspiring to rig bids for oil and gas leases in March 2016.
He died the following day in a car accident.
Fortune: $65 billion
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The late Bernard Madoff made his billions as a high-flying financial adviser as part of securities firm Bernard L. Madoff Investment Securities.
In 2009, he was charged and pleaded guilty to defrauding investors to the tune of around $65 billion (£50bn), running the largest Ponzi scheme on record over at least two decades.
He was sentenced to 150 years in a maximum-security prison and he died behind bars in April.
Fortune: $4.5 billion
Charged with 'massive fraud'
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Elizabeth Holmes was initially praised as the CEO of Theranos, an exciting start-up that promised to revolutionise medical testing with inexpensive blood tests. Her 50% stake in the company was worth an estimated $4.5 billion (£3.5bn), and at the time 19-year-old Holmes was named by Forbes as America's richest self-made woman.
However, a series of allegations surrounding Theranos' frauduent claims and 'major inaccuracies' in the testing it was doing on patients followed, and Holmes' future fell apart. She and her company were charged with 'massive fraud' and her net worth was listed at zero by Forbes. She is currently awaiting trial.
Fotrune: $30 billion
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Once the richest man in Brazil and the seventh-richest man in the world, Eike Batista largely made his money via his Brazilian natural resource company. He was worth more than $30 billion (£23bn) in 2012.
But in the next two years he lost almost all of his wealth, according to CNBC. In fact, in 2013 alone he kissed goodbye to $19 billion (£14.7bn). And he was soon forced to pay massive debts to the bank as his energy-related empire collapsed, finally filing for bankruptcy.
A major victim of the Icelandic banking crisis in 2008
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Bjorgolfur Gudmundsson invested his money from his days as a former soccer player wisely, by plunging it into the beverage business. It turned him into a billionaire with a net worth of $3.5 billion (£2.7bn) and he soon acquired English football club West Ham United and the Icelandic bank Landsbanki.
But he was a major victim of the Icelandic banking crisis in 2008. And he also had a number of bookkeeping offences that cost him a considerable amount of money to fight in the courts.
In 2009, he was declared bankrupt on the basis that he couldn't pay his debts.
Bankruptcy, renowned for her $1 million a month spending.
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The New York-based but Switzerland-born socialite fell into her $2.5 billion (£1.9bn) fortune from a divorce settlement in 1999 when she split from the late billionaire art dealer Alec Wildenstein.
Jocelyn, known as Catwoman due to the excessive work done to her face, has always been renowned for her $1 million (£780k) a month spending.
And in mid-2018, she filed for bankruptcy saying she owed millions, as reported by Fox News. “I was as surprised as anyone because there’s a lot of things involved,” she admitted at the time.
Fortune: $1.5 billion
He fell on hard times after his now-defunct airline racked up debts
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The party billionaire of the 90s, Vijay Mallya made $1.5 billion (£1.1bn) as India’s richest liquor baron and the owner of Kingfisher Airlines.
But in 2012 he fell on hard times after his now-defunct airline racked up debts of more than $1 billion (£778m).
His lavish spending saw him actually owe the banks money, but he left India quickly.
The banks are on his back though, as the embattled tycoon is currently fighting an extradition case in London.