Filing for bankruptcy carries a heavy stigma but when individuals find they can't settle their liabilities it can be the only option. Disastrous risk-taking, dodgy dealing, runaway spending, a hefty tax bill or just plain bad luck can propel a person into financial hell, and the richer they are, the harder they fall. Adjusting their sky-high debt levels for inflation, click or scroll through 30 prominent people who went spectacularly bankrupt.

Though not bankrupt in the modern sense of the term, Abraham Lincoln was left high and dry in 1833 after borrowing $1,000 to purchase a general store in New Salem, Illinois. The business tanked the following year and Lincoln was unable to pay off the debt. His two remaining assets – his horse and surveying equipment – were confiscated, and it took the future president several years to settle his liabilities.

Other presidents who were left 'bankrupt' either before or after their stint in the White House include Thomas Jefferson, James Madison and Ulysses S. Grant. While Donald Trump filed for Chapter 11 bankruptcy on six occasions, he did so on behalf of his businesses, and has never declared personal bankruptcy.

Screen siren Veronica Lake, who is famed for her femme fatale roles in 1940s movies including This Gun for Hire and The Blue Dahlia, not to mention her much-imitated wavy hairstyle, had a serious alcohol addiction that contributed to her decline as a star. Lake declared bankruptcy in 1951 at the end of her film career.

The tragic actress had debts of $156,574 against assets of $168,050, and her home was seized by the Internal Revenue Service (IRS) due to unpaid taxes. Lake had a stint as a cocktail waitress in the early 1960s, but returned to acting in 1963, appearing on stage and in several TV shows, but died relatively young at 50 from alcohol-related illness.

The younger brother of Backstreet Boy Nick Carter, Aaron Carter (pictured with his mother in 2001) followed his sibling into show business and made more than $200 million by the time he turned 18, a staggering sum of money that should have set him up for life. There was just one catch. Carter failed to meet his tax obligations and owed the Internal Revenue Service millions.

The former child star claimed his parents failed to manage his money correctly. In 2013, at the age of 26, Carter filed for Chapter 7 bankruptcy with assets of just $8,232 and debts of $2.2 million, much of which was owed to the US tax authorities. Since then, Carter has been working hard to pay his dues, releasing music and performing in as many shows as possible, but was arrested in 2017 for driving under the influence and marijuana possession.

Great American writer Mark Twain, whose real name was Samuel Clemens, made a good amount of money from writing, but lost a fortune investing in newfangled technologies, most notably the Paige typesetting machine. Twain ploughed $300,000 into the gadget during the 1880s and early 1890s, but was left massively out of pocket when it was rendered obsolete by the Linotype.

In 1894 the Father of American literature declared himself bankrupt in a New York state court. His debts amounted to $100,000, around $2.9 million when adjusted for inflation. Fortunately, Twain recovered financially, with the help of Gilded Age industrialist Henry Huttleston Rogers, and paid back his creditors in full despite being under no obligation to do so.

At the peak of his career, actor and comedian Mickey Rooney had a personal fortune of around $12 million. Yet by the early 1960s, the man Vanity Fair described as “the original Hollywood train wreck” had burned through the lion's share. He filed for Chapter 11 bankruptcy in 1962.

In addition to costly alcohol and drug addictions, Rooney was a compulsive gambler, and his finances were mismanaged to boot. The star never regained his fortune and in 2011 he alleged elder abuse and financial exploitation by members of his family during a Senate Special Committee hearing. The Hollywood icon died in 2014 at the age of 95, leaving an estate valued at just $18,000 and owing medical bills and back taxes.

Founder of the world-famous food giant that bears his name, Henry John Heinz was compelled to declare bankruptcy in 1875 when his condiment business Heinz Noble & Company went into administration following the Panic of 1873. The failure was chiefly due to poor sales of the company's horseradish relish, which was based on his mother's age-old recipe.

Grappling with debts of $160,000 against assets of $110,000, Heinz narrowly escaped jail and even struggled to afford to eat for a time. Luckily, the plucky businessman founded F & J Heinz the following year. He launched the firm's famous Tomato Ketchup not long after and the rest is history.

From tennis court to the UK's High Court, Boris Becker was once estimated to be worth over $131 million but was declared bankrupt in 2017 in London with debts believed to total $4.1 million owed to the private bank Arbuthnot Latham. According to the German press, the six-time Grand Slam champion may owe his many creditors as much as $70.7 million.

Becker's financial nightmare began in 2001 when he was ordered to pay a divorce settlement to ex-wife Barbara and paternity payments to model Angela Ermakova, which totaled $20 million. And it's all been pretty much downhill from there. In a bizarre twist to the saga, the tennis legend tried to claim diplomatic immunity from bankruptcy in 2018 based on his role as attaché for the Central African Republic, but later dropped the claim. In 2019, Becker was charged of hiding assets including a property in Chelsea, London and £1.2 million ($1.7m) in cash. Then in October 2020 Becker was charged for not disclosing his trophies and medals to bankruptcy trustees, as well as sending payments to individuals, although the former tennis star denied this. The trial is planned for September 2021, and if he loses he could face seven years in jail.

Fashion entrepreneur Karen Millen co-founded her eponymous company in 1981 with just £100 ($220) and opened her first store in Maidstone, England in 1983. The British chain expanded throughout the 1980s and 1990s and, by the early 2000s, Karen Millen boasted 130 stores across the world. In 2004, the business was acquired by Icelandic company Mosaic Fashions and Millen cashed in to the tune of £35 million ($65m).

Despite the windfall, Millen ended up in deep financial trouble. The former fashion boss claims she was defrauded by Kaupthing, the failed Icelandic bank that financed the acquisition of her company, and that she was roped into a sketchy tax avoidance scheme, both of which cost her dear. In 2016, Millen was declared bankrupt by the UK's Inland Revenue after failing to pay a £6 million ($7.8m) tax bill.

The second most-charted female artist of all time in the US after the late Aretha Franklin, Dionne Warwick scored 69 singles in the Billboard Hot 100 over her long career. In spite of her incredible chart success, the six-time Grammy Award-winning artist had no choice but to file for Chapter 7 bankruptcy in 2013, citing $10.7 million debts. That's the equivalent of $11.6 million today. 

Warwick claimed her finances were grossly mismanaged over a number of years, and that those in charge failed to settle bills of just under $7 million owed to the US tax authorities. The That's What Friends Are For singer is currently suing the Internal Revenue Service over the matter.

Actor Burt Reynolds died in 2018 and left the world with a respectable net worth of $5 milllion, but the Smokey and the Bandit and Boogie Nights star had plenty of financial headaches to deal with during his life, which nevertheless he resolved. After his costly divorce from Loni Anderson in 1993, Reynolds' finances took a turn for the worse.

A failed restaurant venture and a propensity for overspending – Reynolds allegdly shelled out $100,000 on toupees for instance to hide his bald patch – didn't do him any favors either, and the actor, who dominated the box office in the 1970s and 1980s, filed for Chapter 11 bankruptcy in 1996 with debts of $10 million. That's the equivalent of $16.1 million today.

The co-founder of General Motors, William Durant was hit especially hard by the Wall Street Crash of 1929 and ensuing Great Depression, which resulted in the collapse of Durant Motors, the firm he established in 1921 after he was pushed out of General Motors. The company went out of business in 1933.

Durant was also a major stock market player during the 1920s, which magnified his losses following the Wall Street Crash. The automobile pioneer was declared bankrupt in 1936 with debts of $914,000. His only assets were $250 worth of clothing. Durant and his wife Catherine were thankfully saved from penury by a General Motors pension that amounted to around $173,000 a year in today's money. He died in 1947.

Heir to the A&P grocery store empire, Huntington Hartford II was bequeathed $90 million in 1922. The hapless scion pumped millions into a series of failed projects, from a money pit art gallery and modeling agency to a disastrous resort project in the Bahamas that lost $30 million.

Hartford declared bankruptcy in 1992 with debts of up to $9.9 million and assets totaling up to just under $1 million. Down and out, he lived alone in a rundown rented house in Brooklyn before his daughter Juliet whisked him off to the Bahamas, where he died in 2008, leaving the world considerably poorer than when he arrived.

Breaching a major Hollywood contract can lead to financial ruin as A-lister Kim Basinger discovered when she pulled out of the movie Boxing Helena. Ruling against Basinger, a court awarded Mainline Pictures $8.1 million. As a consequence, the star filed for Chapter 11 bankruptcy in 1993, citing debts of $11 million (£7.6m) and assets of up to $3 million. The breach of contract debacle was eventually settled for $3.8 million.

Adding to her woes, Basinger had snapped up the town of Braselton in Georgia for $20 million in 1988, hoping to turn it into a movie-themed tourist attraction, but the project fell through. She ended up offloading the town in 1994 for a hugely marked-down $1 million, but eventually bounced back, and it has been reported that she is worth as much as $40 million.

Superstar of the early 1990s and wearer of parachute pants, MC Hammer, aka Stanley Kirk Burrell, was earning $33 million a year at the height of his fame. The U Can't Touch This singer may have been pulling in serious cash, but he was spending it like water. As well as dropping $500,000 a month for a staff of 200, Hammer snagged a sprawling estate and installed gold-plated gates, a recording studio, swimming pools and a movie theater.

The R&B star's spending knew no bounds, and he splashed millions on luxury sportscars, racehorses and more. When his career waned in the mid-1990s, the cash ran dry, and Hammer entered Chapter 11 bankruptcy protection in 1996 with debts of $13 million and assets of $1 million. The case was converted to Chapter 7 bankruptcy in 1998.

Former Atlanta Falcons player Michael Vick was one of the world's highest earning sportspeople during the mid 2000s, pulling in an estimated $25.4 million a year. But the NFL star sabotaged his career and fortune in 2007 after getting involved in an illegal dog-fighting ring, which horrified America.

Vick pleaded guilty to participating in the cruel dog-fighting operation and served 21 months in prison. He was fired by the Falcons and filed for Chapter 11 bankruptcy in 2008 with debts of $17.6 million against assets of $16 million. Vick returned to playing pro football and retired from the NFL in 2017, but never fully regained his reputation or his fat paycheck.

Hell-raising boxer Mike Tyson made a whopping $300 million during his 20-year career in the ring, but pretty much blew the lot. His most ridiculously over-the-top purchases included a $2 million bathtub, 110 luxury cars, a gold and diamond chain worth hundreds of thousands of dollars and three white Bengal tigers priced at $70,000 each.

Tyson's crazy overspending caught up with him in the early 2000s, and he filed for Chapter 11 bankruptcy in 2003 with $23 million in debts. His main creditors were the US Internal Revenue Service and the UK's Inland Revenue, as well as various state treasuries and law firms.

Las Vegas stalwart Wayne Newton has raked in millions performing in the City of Sin and was ranked the world's highest paid entertainer by Forbes in 1983, but he was up to his eyeballs in debt by the early 1990s. Newton part-owned the city's Aladdin Hotel 10 years previously, and had attempted to sue NBC for libel over the deal. The veteran entertainer claimed NBC had reported that he'd teamed up with the Mafia to buy the hotel.

Newton was unsuccessful in his efforts to sue the TV network and racked up millions of dollars in legal fees, which left him in financial dire straits. As well as the legal troubles, the Las Vegas performer had made several bad investments during the 1980s. He filed for bankruptcy in 1992, citing $20 million in debts. Fortunately, Newton was back on his feet again financially by 1999.

50 Cent's legal wranglings got him into hot water and he had to file for Chapter 11 bankruptcy in 2015. Though he claimed assets of up to $50 million against debts of $36 million, the rapper, producer and entrepreneur, whose real name is Curtis James Jackson III, had been hit with legal fees and judgements totaling $20 million.

The judgments against the rapper ranged from a $6 million award to rapper Rick Ross's former girlfriend Lastonia Leviston for posting an intimate tape of her online without her consent, to $17.2 million issued to a business partner who accused 50 Cent of stealing the design of his Sleek by 50 headphones. He has since cleared his debts, helped by a payout of $13.65 million from lawyers after he won a legal malpractice lawsuit.

The Republican Governor of Arizona from 1991 to 1997, Fife Symington filed for Chapter 7 bankruptcy in 1995 early into his second term. The businessman and politician had amassed debts of $24 million as a result of the collapse of his real estate investments and had assets totaling just $61,000.

The following year, a spotlight was shone on Symington's real estate dealings and he was indicted on 21 counts of extortion, making false financial statements and bank fraud, for which he was convicted in 1997. The conviction was however quashed in 1999 and Symington was pardoned by President Bill Clinton in 2001.

Socialite Patricia Kluge married America's one-time richest person John Kluge (pictured), who was 34 years her senior, in 1981. When the couple divorced in 1990, the former model was awarded a generous cash settlement of $1 million a year along with the lavish Albemarle estate in Virginia, which was once valued at a cool $100 million.

With ambitious plans to set up a winery business, Kluge massively over-leveraged, and was plunged into debt following the 2008 crash. Despite selling off Albemarle and her vineyard concern, which were purchased at a knockdown price by her fr-enemy Donald Trump, the hard-up socialite had to file for bankruptcy in 2011 with liabilities of up to $50 million against assets of up to $10 million.

After hanging up his bat and cleats and calling time on his baseball career in 1998, former New York Met and Philadelphia Phillie Lenny Dykstra tried his hand at running a car wash, managing a stock portfolio and flipping NHL star Wayne Gretzky's mansion, but his attempts to hit a home run with his finances failed miserably.

Dykstra filed for Chapter 11 bankruptcy in 2009 with debts of up to $50 million against assets of just $50,000. The case was converted to Chapter 7 bankruptcy the following year and in 2012, the ex-baseball star was sentenced to three years behind bars for grand theft auto and filing a false financial statement. He served six and a half months, before his release in July 2013.

Another star who got into trouble for not paying his taxes, country singer Willie Nelson filed for Chapter 11 bankruptcy in 1990 with up to $32 million in debts to the Internal Revenue Service. The organisation seized the star's six properties and other assets including master tapes, platinum records and clothing.

Nelson was eventually stung for $16.9 million by the service and released the album The IRS Tapes: Who'll Buy My Memories in 1992 to help pay off the debt. In 1993, Nelson settled for a bargain $9 million, and today the country music veteran is worth a very respectable $15 million.

Un-break My Heart singer Toni Braxton was left broke in the mid 1990s after her record company awarded her a pathetic $2,000 in royalties despite the artist selling 40 million records. Though her overspending wasn't as extravagant as the media claimed at the time, it didn't help and she filed for Chapter 7 bankruptcy in 1998 owing a total of $3.9 million.

Braxton had to sell her Grammys and American Music Awards to help make ends meet and endured a humiliating interview with Oprah Winfrey, who castigated her for mismanaging her finances. The singer declared bankruptcy again in 2010 with debts of $18.3 million against assets of up to $1.6 million, this time due to medical problems. Sadly her money woes haven't stopped there, and in 2019 it was revealed that Braxton owed $340,252.99 in back taxes to the IRS and $116,154.64 to the State of California Franchise Tax Board for 2017.

Born Wilhelm Fuchs, William Fox founded what would become 20th Century Fox in 1915, building the firm into a major movie studio, but his fortunes went south after he bought a stake in rival studio Metro-Goldwyn-Mayer, angering its boss Louis B Mayer, who used his high-level connections to persuade the Justice Department to sue Fox for breaking antitrust laws.

The antitrust case dented his fortune, which was further depleted by the Wall Street Crash and a car accident injury that rendered him unable to work. The Hollywood mogul lost control of the Fox Film Corporation in 1930 following a hostile takeover and filed for bankruptcy in 1936 with debts of $9.5 million. Fox was imprisoned in 1942 for attempting to bribe a judge during his bankruptcy proceedings, and faded into obscurity thereafter.

Clint Murchison Jr was awarded a bumper inheritance of $200 million when his oil tycoon father died in 1969. Having founded the Dallas Cowboys NFL team, Murchison channelled millions into a series of ill-judged investments, including questionable real estate, loss-making restaurants and even a pirate radio station.

Needless to say, the spendthrift heir ended up having to file for bankruptcy protection in 1985 with debts of $397 million and assets of $70.8 million. Suffering from a rare nerve disorder and confined to a wheelchair, Murchison was forced to sell off assets including his beloved childhood home, and died two years later, no doubt a broken man.

America's all-time biggest bankruptee, Texan commodities baron and thoroughbred horse owner Nelson Bunker Hunt came a cropper when his attempt to corner the global silver market during the 1970s failed on an epic scale. By 1979, Hunt (pictured with Queen Elizabeth II in 1974) had amassed up to $4 billion worth of the precious metal, representing what many estimated as half of the global supply.

Hunt, who was once considered the planet's richest person, lost out big time when the price of the commodity plummeted on so-called Silver Thursday in 1980. He went on to file for bankruptcy in 1986 with $500 million in debts and $100 million in assets, and even had to sell off a $20 teapot at one point.

 

Sigurdur Einarsson is the disgraced former chairman of Kaupthing Bank, the defunct bank Karen Millen claims she was defrauded by, and the subject of Iceland's biggest personal bankruptcy case. Dubbed a modern-day “raiding Viking”, Einarsson was one of the architects of the Nordic nation's severe financial crisis, which raged from 2008 to 2011.

The country's most disreputable banker, Einarsson was sentenced to five years imprisonment in 2013 (later reduced to four years) for manipulating the markets, and was declared bankrupt in 2015 with debts of $2.1 billion.

In what became Australia's most infamous individual insolvency case, controversial businessman Alan Bond, who had significant interests in sport, media and mining, filed for bankruptcy in 1992, after failing to settle a personal guarantee on a loan for a mining venture totalling $137.3 million.

Bond's debts amounted to the equivalent of $1.8 billion, which works out at $3.2 billion when adjusted for inflation. The British-born executive was later jailed for seven years for deceptively siphoning off an immense amount of money from one of his companies to another.

Ireland's one-time richest person, Seán Quinn had a personal fortune of $6 billion in 2008, according to Forbes. The rags-to-riches tycoon started out with a humble gravel business which he grew into a colossal conglomerate spanning construction, manufacturing, real estate, insurance, and more. 

The tycoon had invested heavily in the Anglo Irish Bank using risky financial instruments and lost bewildering sums of money when its share price collapsed following the 2008 crash. Quinn's liabilities totaled $3.2 billion and the magnate was declared bankrupt in 2011 in Northern Ireland and in 2012 in the Republic. Compounding his fail from grace, Quinn went on to serve nine weeks in prison for asset-stripping and non-cooperation with the banking authorities.

Now read: Billionaires behind bars