Home Billionaires 25 Business Tycoons Who Destroyed Their Own Empires

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25 Business Tycoons Who Destroyed Their Own Empires

Trista November 30, 2020

Nearly everybody dreams of one day becoming rich. Young adults often attempt to find the fulfillment of that dream by chasing the perfect job and the illusion of success. Unfortunately, people are guided by a culture that values the latest self-made multi-millionaire, even if that sudden wealth means they became tycoons via unethical means. Moreover, when that wealth vanishes overnight, the media pounces on the disgraced millionaire or billionaire.

There are many who were in yesterday’s Fortune 500 are now in jail or facing lifetimes of ignominy. Furthermore, take their failures as a lesson. It may be best if you value the integrity of the people around you more than the fast and glitzy life of those who seem to be overnight successes. Read ahead to see how 25 business tycoons destroyed their own empires according to How They Blew It by Jamie Oliver and Tony Goodwin.

A picture of the onetime billionaire Jocelyn Wildenstein. Credit: Shutterstock

25. Jocelyn Wildenstein

Wildenstein was once worth billions of dollars due to her marriage to billionaire art dealer Alec Wildenstein. Wildenstein was a New York socialite who lived the lavish life of a billionaire in every way possible; parties, luxury homes, extensive cosmetic surgery, and more. However, when she and Alec Wildenstein divorced, her luxury lifestyle quickly collapsed. She spent the entire sum of more than 2.5 billion she received in a divorce settlement and had to turn to two pieces of supposedly priceless art for support. However, it turned out the Diego Velazquez painting was a forgery, and the Paul Cezanne she was given sold for far less than it was appraised for.

A Paul Cezanne painting. Credit: Shutterstock

When Wildenstein filed for Chapter 11 bankruptcy in 2019, she reported that she had $0 in her checking account. Her only source of income was $900 per month in Social Security payments and assistance from friends and family. Despite her newfound poverty, she was still able to retain expert legal aid and is seeking more assets from her billionaire ex-husband to achieve what, in her words, she feels she deserves for her lifetime. A judge has stipulated she cannot use any further payments from her husband’s estate for additional cosmetic surgery, thanks to her shocking appearance that has led her to be called “Catwoman” and the “Bride of Wildenstein.”

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Huang Wenji made his fortune in umbrella manufacturing. Credit: Shutterstock

24. Huang Wenji

China has a notoriously volatile stock market, and nobody exemplifies the rollercoaster ride of the Eastern market better than Huang Wenji. He is the 75% owner and chairman of the China Jicheng Holdings, which owns umbrella manufacturing factories. During a recent stock market drop, the company’s stock lost 91% of its value in one day. On that single day, Wenji and his wife, who co-own the 75% controlling share, lost over 1.9 billion dollars of their wealth. In 2019, the company posted a historic record loss of 16.2 million dollars in addition to its stock market woes.

The Hong Kong stock exchange. Credit: Shutterstock

The China Jicheng Holdings company has never recovered. It is still trading at pennies on the former dollars of its old strength. As of November 2020, Huang Wenji’s controlling company was seeking to consolidate and dump shares in an attempt to recoup at least some money out of the struggling company. While it still exists and is making products, it is merely a shell of the former power it once was, thanks to Hong Kong’s volatility. The China Jicheng Holdings company is far from the only company that has been broken by this volatility, and many see wealth evaporate on the market overnight.

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Allen Stanford ran what amounted to a Ponzi scheme. Credit: Shutterstock

23. Allen Stanford

While many of the former billionaires on this list lost their vast sums of personal wealth, very few lost their freedoms or faced any actual legal consequences. That is not true for Stanford, who, in addition to losing billions, is currently serving a 110-year sentence in federal prison after being convicted on multiple counts of massive financial fraud including running a Bernie Madoff-like Ponzi scheme. What started as a simple business, founded with his father, buying depressed real estate and selling it for a profit later when markets rebounded soon became a massive financial services empire known as Stanford Financial Group.

Stanford is serving a 110-year sentence at a federal penitentiary. Credit: Shutterstock

At its height, Stanford Financial Group was supposedly worth 8.5 billion dollars and boasted over 30,000 clients in at least 136 countries around the world. However, when subjected to scrutiny, the Security Exchange Commission (SEC) found that Stanford Financial Group had illegally sold $8 billion in high-yield certificates of deposit in what amounted to a Ponzi scheme. The Stanford Financial Group did not have $8.5 billion in assets under management and was virtually broke. Stanford was eventually charged with wire fraud, money laundering, obstruction of justice, and numerous other charges leading to his 110-year sentence.

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A picture of the once-wealthy Mallya. Credit: Shutterstock

22. Vijay Mallya

No name was more associated with Indian wealth and luxury than Mallya, who was actually once known as the “King of Good Times” in the country. At only 28 years old, he took over his father’s relatively small liquor company and turned it into a vastly profitable industry, amassing over $1.5 billion in personal wealth. As his business and personal wealth kept expanding, he kept acquiring more properties, including the airline Kingfisher Airlines. As with many other billionaires fallen from grace, Mallya simply grew too quickly. It tried to take on too many properties and projects at once.

A Kingfisher Airlines plane. Credit: Shutterstock

Airlines are a notoriously tricky enterprise to run, and Mallya’s Kingfisher Airlines was no exception. He quickly accumulated debt from keeping the airline running, which eventually led to his losing the controlling stake in his father’s inherited United Spirits liquor company. Facing millions in debts with no way to pay them back, Mallya fled from India to the United Kingdom, hoping to find refuge from his obligations. He has been the subject of extradition hearings for some time now, with India attempting to recall him to the country to face charges related to his vast sums of unpaid debts.

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Donald Trump purchased Kluge’s Virginia property. Credit: Shutterstock

21. Patricia Kluge

Another billionaire through marriage, Kluge was married to one of the world’s wealthiest men, John Kluge, who had a personal fortune of around $5 billion. However, when they divorced, she was left with only about $1 million in a trust and a single luxury countryside property called Albemarle in Virginia. Seeking to reach the former glory of her billionaire lifestyle, Patricia took out a loan of $65 million, using the mansion and property as collateral. She used it to start a business building luxury homes. She also used it to expand the vineyard and winery on her Albemarle property into a world-class facility.

The tasting room at the former Kluge winery, now owned by Donald Trump. Credit: Shutterstock

Unfortunately, Kluge and her third husband quickly defaulted on these loans when they did not receive the expected return on investment. Donald Trump, a friend of both Patricia and her ex-husband John, offered to buy the foreclosed property from Bank of America. He eventually won through a bidding process, acquiring the entire property including the bank’s winery. The property became known as the Trump Winery, a title it continues to carry today and is the largest winery in Virginia. The vineyard and winery make about 36,000 cases per year and is the most extensive French vineyard acreage on the East Coast.

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Yahoo! was one of Amerindo Investment Advisors’ largest holdings. Credit: Shutterstock

20. Alberto Vilar and Gary Tanaka

Vilar and Tanaka were once poster children of the thriving investment company industry. Amerindo Investment Advisors had at its height a net worth of over $1 billion. They made considerable investments in technology companies during the dot-com bubble of the late 1990s and suffered some of the bubble’s worst consequences when it burst in 2000. The “Amerindo Technology Fund” invested in numerous tech start-ups and once had Yahoo! Mail and internet services as over 40% of its tech portfolio. Amerindo achieved a great deal of its wealth by offering investors supposedly stable, high-return investment over fixed terms.

The logo of the United States Securities and Exchange Commission. Credit: Shutterstock

In reality, Vilar and Tanaka were investing customer funds in extremely risky tech start-ups, the vast majority of which crashed when the dot-com bubble burst, leaving them unable to pay returns on any of their investors’ deposits. By 2005, the Securities Exchange Commission (SEC) completed an investigation, charging both Vilar and Tanaka with money laundering, wire fraud, conspiracy to commit securities fraud, securities fraud, investment advisor fraud, and more. Vilar was sentenced to a ten-year prison sentence, one of the few fallen billionaires who faced serious consequences for his actions, which defrauded thousands of investors of their money.

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An Anglo Irish Bank branch under construction in Dublin. Credit: Shutterstock

19. Sean Quinn

Quinn was once Ireland’s richest man with a personal wealth of over $6 billion at the height of his success in 2005. However, he lost the vast majority of his wealth in the 2008 financial crisis that was caused by a combination of the US subprime mortgage crisis and the corruption and failure of Iceland’s national banks. Quinn accumulated his wealth through his holding company, Quinn Group, which purchased numerous companies throughout Europe, including the Irish companies Bupa Ireland, a private medical insurance company, multiple manufacturing companies, hotels, diverse real estate and development properties, and the Anglo Irish Bank.

Irish manufacturing was a large part of Quinn’s holdings. Credit: Shutterstock

When the European banking industry took a massive hit in 2008 as part of the crisis started by Iceland’s national banking collapse, Quinn lost the vast majority of his wealth due to incredible losses by the Anglo Irish Bank. He was fined over 3.25 million Euros in 2008 by Irish financial regulators as part of an investigation into favorable insider loans issued to his insurance business by his bank. By 2011, Quinn had filed for personal bankruptcy due to a combination of continued business losses from the ongoing financial crisis as well as corporate fines from numerous fraud charges.

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The Icelandic economy was at the center of the 2008 financial crisis. Credit: Shutterstock

18. Bjorgolfur Gudmundsson

The banking crisis of 2008 began in Iceland, where rampant fraud and corruption eventually led to the collapse of Iceland’s three national banks. It should come as no surprise then that Icelandic billionaires had some of the most dramatic losses of their fortunes. Gudmundsson was Iceland’s second wealthiest person before the 2008 collapse, with a personal net worth of around $1.1 billion. In 2002, his wealth greatly expanded when he acquired about 45% of Landsbanki shares, one of Iceland’s three national banks. This move positioned him as the 1,014th richest person in the entire world.

His investment in Icelandic banks made Gudmundsson a billionaire. Credit: Shutterstock

When the banks of Iceland fell after years of corruption and fraud, Gudmundsson quickly went down with them. His net worth fell from $1.1 billion to an official $0 on paper. He declared personal bankruptcy in 2009. However, in an example of the staggering resilience that can be bought with billions, Gudmundsson’s son, Thor Bjorgolfsson, has already regained billionaire status, the first person in Iceland to do so since the 2008 collapse. It seems quite possible that at least some of Gudmundsson’s wealth was hidden away by his son before declaring bankruptcy for his son to have rebounded so quickly.

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Here is Elizabeth Holmes, the co-founder of Theranos. Credit: Shutterstock

17. Elizabeth Holmes

Few cases of lost wealth are as dramatic or fascinating as that of Holmes, the lauded young entrepreneur whom many heralded as a reincarnation of Steve Jobs. A notion egged on by Holmes herself, who spoke in an odd, low voice and dressed similarly to Jobs in black turtlenecks and jeans. Holmes was the founder of Theranos, a medical technology company that promised extensive blood testing with a device that would require only a tiny amount of blood. She became the world’s youngest self-made female billionaire in 2015, and at its height, Theranos reportedly had a fortune that was valued at over $9 billion.

Theranos was supposed to revolutionize blood testing. Credit: Shutterstock

However, questions soon began to surround the company as scientific and financial questions were raised about the company and its promised technology, which had never been exposed to peer review, a standard for any scientific development. Amid the investigations, Forbes devalued Holmes’ wealth at zero. Theranos ceased operations in 2018, and Holmes has been banned from holding any part in the company for at least two years by the Centers for Medicare and Medicaid Services. Holmes is still waiting to stand trial on charges of wire fraud and conspiracy as of 2021 thanks to delays from the ongoing pandemic.

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A disgraced billionaire leaving police headquarters. Credit: Shutterstock

16. Eike Batista

Batista became an incredibly wealthy man thanks to his massive investments in Brazil’s expanding mining and oil exploration industries, many of which directly conflicted with Brazil’s indigenous populations. He had a personal wealth of $30 billion at his height and was the wealthiest man in Brazil and the eighth-wealthiest on Earth. However, Brazil was headed for a crash in its mining and oil exploration industries, and that crash would take Batista down with it. By 2013, it was reported that Batista had lost nearly $20 billion of his wealth in just the year 2012 alone.

Batista made his fortune in the mining and oil industries. Credit: Shutterstock

By 2014, his companies continued to hemorrhage stock value and profits, causing his wealth to fall to an estimated $200 million from its height of $30 billion just three years earlier. By the next year, he not only had no personal wealth remaining but was also in debt. In January 2017, Eike was detained by Brazilian police on charges of money laundering. Operation Car Wash was a $100 million money-laundering operation that included Batista and eight others. Batista was also found guilty of bribing a Rio de Janeiro governor and sentenced to 30 years in prison, a case his lawyer is appealing.

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Chris Foster made his fortune in insulation manufacturing. Shutterstock

15. Chris Foster

One of the most macabre stories of business tycoons who destroyed their own empires is that of Chris Foster, who also destroyed his family. After growing up in England with a modest lifestyle, Foster got a job selling used pizza boxes to use insulation, and it inspired him. Foster created insulation for valves in oil rigs to protect them if the entire rig went up in flames. He had a great idea and created a working product, but he had to prove that it worked to convince buyers. He mortgaged his house for $5000 to buy enough gas to make a big enough fire to show that his insulation would be successful. It was.

Foster burned his home down around himself. Credit: Shutterstock

Foster soon had so much money that he didn’t know what to do with it. He began buying luxury sports cars. He purchased horses for his daughter and took up the expensive shooting hobby. Foster came to see himself as above the law and began engaging in questionable business practices, including tax evasion. He soon lost his business but, refusing to admit that anything was wrong, boasted about having a multimillion-dollar contract with Russians. Foster was millions of dollars in debt. Unable to see a way out of his troubles, Foster took the guns he used for hobby shooting and shot the horses and dogs that his teenage daughter prized. He then went inside, shot his wife and daughter, and set his house on fire before killing himself.

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A Bentley, Singh’s car of choice. Credit: Shutterstock

14. Reuben Singh

The Guinness Book of World Records once labeled Singh the youngest self-made millionaire after starting his first business while still in high school and earned millions before his twentieth birthday. However, bankruptcy proceedings in 2007 revealed that all of his wealth was a sham. The flamboyant businessman drove a brand-new Bentley falsified documents with the Bank of Scotland to obtain a loan for nearly a million pounds. When the loan defaulted, the defrauded bank decided it wouldn’t fall for any more of Singh’s claims. It refused to loan any additional money leaving Singh without any moveable cash assets.

The Royal Bank of Scotland. Credit: Shutterstock

He tried to arrange to pay back the money he owed over two years, but he could not provide a viable means to do that. It turns out, the reason Singh needed the loan from the Bank of Scotland in the first place was that his business empire, whose values he had been inflating for years, was utterly insolvent. One failed venture after another left him deeply indebted. As the scandal with the Bank of Scotland unfolded, his business failures came to light and landed him a permanent place in British ignominy. It was quite the fall from grace for a man formerly known as the British Bill Gates.

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Bernie Ebbers built a telecommunications fortune. Credit: Shutterstock.

13. Bernie Ebbers

Ebbers was born in Mississippi. He began investing in hotels and acquired a string of Best Western inns and a car dealership in nearby Columbia. In 1983, he branched out even further and took over a third-rate long-distance company called LDDS. Ebbers renamed LDDS WorldCom and made its headquarters in Clinton, Mississippi. The telecommunications company became one of the largest in the country. Ebbers became a titan near Bill Gates’ stature within the industry as WorldCom quickly became the second-largest telephone service in the United States, second only to AT&T thanks to history-making multi-billion dollar corporate mergers.

At one time, AT&T was the only telecom larger than WorldCom. Credit: Shutterstock

However, behind the scenes, Ebbers engaged in financial fraud to make the company look more profitable. When the company collapsed under the weight of $11 billion in fraud, stockholders lost everything. Furthermore, many who had invested in the company lost their retirement savings. Ebbers and many of his co-conspirators went to prison. The disgraced Ebbers was given an early release due to declining health, and he died a month afterward. WorldCom’s collapse coincided with the historic dot-com bubble that burst around 2000 as the over-speculation of the burgeoning tech industry collapsed, leading many tech companies to bankruptcy.

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Iceland’s banks were at the heart of the 2008 crisis. Credit: Shutterstock

12. Jon Asgeir Johannesson

Iceland’s banking system was far overstretched in the years leading up to the 2008 financial crisis and hit particularly badly when banks worldwide began to collapse. The number-one culprit was that of Icelandic banks’ corruption. At the center of one of these corrupt borrowing networks was Jon Asgeir Johannesson. Johanneson ran a company called Baugur. The man was worth about a billion dollars. Nevertheless, when Iceland’s banks went under during the financial meltdown, Baugur failed. While he was living an outlandish lifestyle with huge yachts and panic-room equipped New York City apartments, Johannesson owed over 1 billion dollars to the three national banks of Iceland.

An Icelandic national bank. Credit: Shutterstock

Allegedly one of Iceland’s three central banks, Glitnir, illegally lent Johannesson about two billion dollars a year before the meltdown. Unethical proceedings between Johannesson’s company and Glitnir over the next year, Johannesson treated the bank as his account, helped both Glitnir and Baugur collapse. The disgraced Johannesson faced the destruction of his corporate empire and criminal charges related to financial fraud and corruption. After his company’s failure, he owed about as much money as 80% of the entire country of Iceland’s GDP to its national banks. Despite the level of fraud and the economic disaster that followed, Johannesson was charged with very few crimes.

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The Lehman Brothers banking logo. Credit: Shutterstock

11. Richard Fuld

Lehman Brothers were one of those banks that engaged in the unethical lending that led to the 2008 financial crisis, and at the helm was CEO Richard “Dick” Fuld, known colloquially as the Gorilla of Wall Street. Fuld did more than allow Lehman Brothers to extend these mortgages to the country’s poor. He allowed Lehman Brothers to fund banks all over the country that were issuing subprime mortgages. The subprime mortgage crisis was fueled by banks issuing adjustable-rate mortgages, which have ballooning interest rates over time, to homeowners with poor credit and low financial literacy, leading to an epidemic of people who couldn’t pay their mortgages.

The Lehman Brothers became an infamous icon of the collapse. Credit: Shutterstock

In return, Lehman Brothers turned all of its toxic assets, including subprime mortgages, along with the money it had loaned to other banks to make their own subprime mortgages and turned them into bonds. Fuld then had the bank pass those bonds, massive IOUs, over to investors who held shares in Lehman Brothers. Lehman Brothers became a casualty of the financial meltdown. It held so many toxic assets that it would collapse no matter what, and its collapse nearly took down all of Wall Street. Fuld had made half a billion dollars building this financial empire, but he is forever disgraced.

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James Cayne also ran a bank that collapsed in the 2008 crisis. Shutterstock

10. James Cayne

Trading in hedge funds ultimately took down Bear Stearns. This process involved using high levels of debt to make investments in the hopes of realizing large gains. Bear Stearns had survived the Great Depression of the 1930s, but its hedge funds were trading mortgage securities that were essentially toxic assets of the subprime mortgage scheme. By the middle of 2007, Bear Stearns was bleeding cash. By 2008, its profitability had halved. The bank could no longer raise the capital that it needed to remain solvent. It became another major loser in the historic 2008 subprime mortgage crisis and resulting recession.

Bear Stearns’ downfall was a historic banking failure. Credit: Shutterstock

At the center of the collapse was James Cayne, the CEO. By the time he resigned at the beginning of 2008, the bank could no longer afford to open. The Federal Reserve had to bail out Bear Stearns, an extremely controversial move because it used taxpayer money to recover a bank that had caused the financial crisis for the first time. However, without the bailout, Bear Stearns’ toxicity would have spread to every other bank on Wall Street. Cayne, who had signed off on the bank’s engagement with subprime mortgages’ toxic assets, had once held over a billion dollars’ worth of the bank’s wealth. After he resigned, authorities did not charge him. However, he did lose almost all of his wealth.

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One of Merckle’s largest holdings was Volkswagen. Credit: Shutterstock

9. Adolf Merckle

When German business mogul Adolf Merckle did not come home in January 2009, his family called the authorities. Authorities found his body at the train tracks after Merckle had committed suicide by throwing himself in front of a train. The billionaire entrepreneur ran the holding company VEM Vermoegensverwaltung which, among other companies, held troubled German automaker Volkswagen. Nevertheless, Volkswagen was one of many companies that faced market turbulence as the financial crisis began. Merckle was born into a wealthy family and worked in business all his life. At his highest point, he was the world’s 36th richest man and the fifth richest in Germany.

The company’s value was falling as the crisis’s strain began reverberating worldwide. Merckle tried unsuccessfully to acquire the credit that he would need to keep VEM afloat, but German banks had also fallen victim to the unfolding crisis. By the time Merckle took his life, Volkswagen had lost millions in its value, and VEM shares were dropping precipitously. He was one of many businessmen who became a casualty of the financial crisis by deciding, sadly, that the only way out was to end his own life. His son, Ludwig Merckle, took over the family business and cleared debts by offloading a pharmaceutical company. He’s currently worth roughly 5 billion US dollars.

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Mikhail Khodorkovsky was once the wealthiest man in Russia. Credit: Shutterstock

8. Mikhail Khodorkovsky

Also known as Citizen K, Mikhail Khodorkovsky now lives in exile in London. Growing up as a young businessman in the 1980s, Khodorkovsky was an ardent communist. Khodorkovsky began his business ventures by opening up a coffee shop during the 1980s. Moreover, he became immensely successful. Just before the fall of the Soviet Union, in 1989, Khodorkovsky and his partners founded Menatep, a private bank that would not only survive but thrive against the collapse of Russia’s state-owned banks. An exceptional rarity in Russia, Menatep held the controlling assets of the oil company Yukos.

A protest to free Khodorkovsky. Credit: Shutterstock

Then Vladimir Putin came into power, and Khodorkovsky challenged him. Repeatedly. He funded independent media outlets and other venues of democracy, and he even flirted with the idea of challenging Putin for the presidency. Putin made an example of Khodorkovsky by sentencing him to prison for crimes that could not be proven. Guards brutalized him and his fellow prisoners, some to the point of death. However, Khodorkovsky got a lucky break shortly before the 2014 Sochi Winter Olympics. Putin pardoned some political prisoners in a farce humanitarian display to the world. Khodorkovsky, who had once been the richest man in Russia and the oligarch of a banking and oil empire, became an exile in London. He continues to live there, promoting human rights and democracy.

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Boris Berezovsky’s massive yacht. Shutterstock

7. Boris Berezovsky

Mikhail Khodorkovsky and Boris Berezovsky were the so-called Russian oligarchs who built their business empires in the waning days of the Soviet Union and became power brokers post-Soviet Russia. Berezovsky set up a car company called LogoVaz in 1989. Soviet leader Mikhail Gorbachev had legalized small businesses run by private interests. LogoVaz became the first capitalist-style car dealership of the Soviet Union and a launching pad to expand into banking and oil. Berezovsky even became the controlling interest in Aeroflot, the state airline for the Soviet Union, and its public television channel.

Berezovsky at a political protest in London. Credit: Shutterstock

However, when Putin came to power in the waning hours of 1999, he swore to put an end to the oligarchs, including Berezovsky, and to reimpose state control over businesses. Berezovsky soon fled to London, where he lived in exile and survived numerous assassination attempts. Like Khodorkovsky, Berezovsky used his time in exile and his immense wealth to promote human rights and support democratic initiatives in Russia. In 2013, he was found dead with ligature marks around his neck, possibly indicating that he had been assassinated by one of Putin’s henchmen.

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Klimt and Naggar amassed a mysterious fortune. Credit: Shutterstock

6. Peter Klimt and Guy Naggar

Putting together a picture of what Dawnay Day was is a bit difficult. The company began under Guy Dawnay and Julian Day in 1928 and became part of Lord Jacob Rothschild’s business portfolio in the 1970s. By the 1980s, it was an empty shell that didn’t do anything. At this point, Guy Naggar bought Dawnay Day, and Peter Klimt joined him in 1992. By 2007, Dawnay Day reportedly had 500 companies in its portfolio, but nobody knows what Dawnay Day was. Naggar called Dawnay Day an internet-based venture capital and corporate finance firm, but that phrase is vague enough to defy any clear explanation. Still, Dawnay Day continued acquiring businesses across Britain and Europe, including hotel chains and restaurants. It turns out, Naggar and Klimt were buying up valuable, profitable companies on debt. After a while, the credit to continue buying up companies on debt ran out.

The 2008 crisis exposed the company’s finances. Credit: Shutterstock

During the financial crisis of 2008, Dawnay Day collapsed under the weight of its own debt. The company was such an elaborate house of cards that its shares began to fall by the time Naggar lost a million pounds for every penny lost in share values. Naggar and Klimt had gambled their entire lives on the bet the world operates in a certain way. They assumed that buying up businesses using debt would build up their corporate empire. Nevertheless, Dawnay Day became a ship riddled with bullets from its massive debts without a strategy for using those businesses.

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Enron and Ken Lay became synonymous with corruption. Credit: Shutterstock.

5. Ken Lay

The Enron scandal unfolded in 2001, and as a result, 20,000 employees lost their jobs. Likewise, many people who invested in the company lost their life savings. It was the largest bankruptcy in American history at that point. The scandal was the product of falsifying account books. It appeared that the company was profitable when it was insolvent. Ken Lay and Jeffery Skilling were at the center of those accounting practices. Lay was the founder and CEO of Enron, and Skilling encouraged falsified accounting. Enron’s collapse had such an impact that Enron became a cultural shorthand in the US for an ill-managed or devious company.

Enron’s former headquarters. Credit: Shutterstock

Up until that point, Lay was one of the highest-paid CEOs in the entire world. Throughout the 1990s, he grew Enron aggressively through profitable deals and rising share values. However, when growth slowed, he and Skilling wanted to keep up Enron’s appearance as one of the country’s fastest-growing companies. The Securities and Exchange Commission became involved when some publicly released financial data didn’t add up. After Enron collapsed, many of its executives faced criminal charges and prison times. Ken Lay met numerous financial fraud accounts, but he died of a heart attack before being sentenced. His name will be forever linked to corporate fraud.

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Zhou Zhengyi made his fortune in exported goods. Credit: Shutterstock

4. Zhou Zhengyi

In 1961, when China was coming out of its communist revolution and entering a period that looked more stable, Zhengyi began a career of stock market speculation and property development in nearby Hong Kong. China’s economy entered a phase of unprecedented growth. Its state-run factories sent Made-In-China products all over the world. However, the communist state, including the state-run economy, was plagued by corruption. Moreover, Zhengyi was one of the few who would face prosecution for his corrupt dealings. In 2007, a court found Zhengyi guilty of giving over $130,000 in bribes to employees of state companies and government officials.

Zhengyi faced charges for his role in the corrupt economy. Credit: Shutterstock

By this time, Zhengyi was the richest man in Shanghai and the eleventh-richest man in China. The severest possible punishment for Zhengyi’s financial crimes was death. Instead, he received 16 years in prison. However, documents show that he had bribed the correctional officers to get more favorable treatment. Then some of those guards received jail time of their own. Ultimately, Zhengyi only spent two months in jail, and he was one of only a few of China’s corrupt businessmen to face prosecution at all. He has been blacklisted in Hong Kong and is unable to engage in any business ventures there.

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Kevin Leech became a dot-com billionaire before falling from grace. Shutterstock

3. Kevin Leech

When Leech was 21, he took over the British funeral parlor that his father ran. Within a few years, he had displayed his business acumen by turning it into a chain of more than three dozen funeral parlors. He used that same business acumen to become one of the billionaires of the dot-com boom in the 1990s. When tech companies saw high stock values in the 1990s, Leech went on to buy a controlling interest in biotech and medical research firms. He also bought up stocks in restaurants, caravan parks, and technology firms throughout American and Europe. To flaunt his newfound wealth, the former undertaker bought a mansion and a private jet.

Zambian children, Leech’s new focus. Credit: Shutterstock

Nevertheless, when the dot-com boom went bust, and share prices collapsed, Leech found himself insolvent. He had borrowed millions of dollars to finance his investments, which had once made him a billionaire but had become worthless. His high-profile bankruptcy proceedings made him one of the most resented people in Britain. He could no longer even get a credit card. Since the shady dealings, Leech has repaired his image and his life by dedicating himself to charity. He cared about AIDS orphans in the African country of Zambia. He is currently working with Hands Around the World to fund children’s wards in Zambian hospitals.

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Tchenguiz had billions. Credit: Shutterstock

2. Robert Tchenguiz

In 1982, he and his brother, Vincent, opened Rotch Property Group. They began filling out an impressive portfolio. Rotch Property Group acquired movie theatres, supermarkets, restaurants, and pubs. It specialized in dealings with luxury flats and hip office spaces. By 2004, the brothers were worth nearly $10 billion and held over 600 buildings in their combined portfolio. They had an extravagant lifestyle to go with their wealth, including multimillion-dollar mansions. Then came the financial crisis of 2008, which hit Icelandic banks particularly hard. The Icelandic bank Kaupthing called in its loans, and the Tchenguiz brothers had $3 billion in loans through Kaupthing.

Tchenguiz continues to struggle with finances. Credit: Shutterstock

Kaupthing ultimately collapsed, and the Tchenguiz holdings went into a trust so the loans could still be repaid. Britain’s Serious Fraud Office began investigating the brothers for fraud associated with the collapse. This office is the equivalent of America’s Securities and Exchange Commission. Numerous rounds of litigation amounted to little more than pointing fingers at different entities involved. Tchenguiz’s finances came under fire again in 2020. The bank underwriting FirstGroup that he owned 7 percent of mostly through debt called in its loans. Tchenguiz insists that FirstGroup is responsible for his losses. Much like how he blames Kaupthing for the scandal that swallowed up Rotch Property Group.

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Madoff’s name became synonymous with financial ruin. Credit: Shutterstock

1. Bernie Madoff

Madoff was a titan of New York finance, even serving for a period as the NASDAQ chairman. However, his infamy lies in his role in swindling thousands of Americans out of their savings, running the most massive Ponzi scheme in history. A Ponzi scheme is a swindle where people who make investments early on are promised substantial profit margins. However, those profits don’t come from any actual income earned from their investments. Instead, the yields are based on future money invested by later investors. Nevertheless, Madoff was savvy about running his Ponzi scheme. He had an air of exclusivity in whom he accepted into his hedge funds. Being a member of one of Madoff’s funds became a sign of prestige. Madoff started building his Ponzi scheme in the early 1980s by promising returns of 10 percent on the investment.

Madoff ran one of the most infamous Ponzi Schemes. Credit: Shutterstock

The scheme went on for nearly 30 years despite publications questioning Madoff’s ethics. Even banks that held Madoff’s accounts ignored red flags suggesting he was laundering money through shell companies. Moreover, according to employee reports, he was instructing his accountants to falsify trading and financial statements. Madoff Securities finally collapsed in the financial crisis of 2008. The extent of the fraud began to come to light. Madoff had taken out huge loans through banks that were now troubled. That included HSBC and Banco Santander. He took them out to pay his investors, but he could not repay the loans or investors. The Ponzi scheme’s extent may never be fully uncovered, but it may have been upwards of $65 billion. Madoff received 150 years in prison for his role in driving the collapse of the global economy.

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