Capitalism can be pretty unfair. When done right, a capitalist system gives everybody a reasonably equal chance of making a fortune. But between inheritances, privilege, and just good old fashioned luck, some people have a much better chance of making it big. And some people, just cheat. And because of them, cynics will always be skeptical of billionaires. It can seem sometimes that nobody makes a billion dollars by playing by the rules. But maybe some do. Surely, there are a few billionaires out there who made their fortunes entirely legally and who are good people who want what’s best for the world. But these guys aren’t them.
In this list, we will run the gamut from greedy businessmen, to ruthless criminal bosses, to outright psychopathic dictators. When you’re a billionaire, life is good. You can live in a beautiful house, attract beautiful women, eat delicious food, and have your enemies killed just for fun. But the bigger they are, the harder they fall. When a billionaire gets into trouble, they can often buy their way out of it, either through bribery or high paid lawyers. But if they can’t, their comeuppance is often humiliating, devastating, and can even be lethal. So if you’re frustrated with the disconnect between how hard you work and your lack of wealth, indulge in some schadenfreude and read about 15 rich men who ran afoul of the law and had to pay for it. Big time.
Note: Unless otherwise stated, all figures are in U.S. dollars.
15 Bernard Madoff
We begin our list with perhaps the most infamous white collar criminal of them all. Bernie Madoff was an American financier worth as much as $823 million at the end of 2008. But that has all changed. No longer does Madoff live in mansions in Montauk or Palm Beach. Now he lives in the decidedly less plush confines of Butner Federal Correctional Institution where he is currently serving a 150 year prison sentence. More important than his work as a financier, stockbroker, and financial adviser, Madoff was a prolific fraudster and was convicted of running the mother of all Ponzi schemes, considered to be the largest financial fraud in U.S. history. A Ponzi scheme is a type of fraud wherein the operator pays investors the money paid in by new investors instead of a proper return on investment. Madoff has claimed that many of his investors must have known of his fraud but kept hiring him to invest their money. The very nature of a Ponzi scheme is unsustainable and when Madoff was finally found out, the amount of money missing was an eye-watering $65 billion.
14 Al Capone
Pretty much everybody is at least vaguely aware of the story of Al Capone. The Italian-American mobster was born in 1899 in Brooklyn and rose through the ranks of organized crime until he became boss of the Chicago Outfit and was eventually arrested in 1931. But not everybody realizes just how prolific and successful Capone was. At its height, Capone’s empire has been estimated to have been worth about $1.3 billion in today’s dollars. That’s one heck of an empire. Capone’s main source of income was running bootlegged liquor during a time when prohibition was the law of the land. Despite Capone’s ruthlessness --he once had seven men killed in broad daylight on St. Valentine’s Day-- Capone was finally nailed on tax evasion charges. He was released after serving eight of his eleven year sentence and was exhibiting signs of syphilitic dementia. He died of cardiac arrest in 1947.
13 Bernie Ebbers
Bernie Ebbers was a Canadian-born telecom mogul until he was found guilty of fraud and conspiracy. Ebbers co-founded the telecommunications company WorldCom and oversaw its rise and success until he amassed a fortune worth about $1.4 billion according to Forbes. Unfortunately, Ebbers did not amass that wealth legally. Ebbers’ shady dealings got him arrested and convicted of securities fraud and conspiracy in 2005 and he was sentenced to 25 years in prison. The WorldCom scandal was the largest accounting scandal in U.S. history until the Madoff case. Ebbers will have to live to at least 86 if he is to have any chance of being a free man once again. Ebbers was known as the “Telecom Cowboy” because, instead of a suit, he often wore boots and blue jeans. Well now, he wears the same uniform every day.
12 Domenico Dolce & Stefano Gabbana
A few years ago, Italy pursued a major crackdown on tax evasion and two of the most noteworthy figures to be charged were Domenico Dolce and Stefano Gabbana, purveyors of the famous luxury fashion brand, Dolce & Gabbana. The two controversial Italian designers are worth around $1.74 and $1.56 billion, respectively. However, in April 2014 they were found guilty of tax evasion to the tune of $570 million and sentenced to 22 months in prison. They appealed that decision and it was overturned by a higher court in October 2014. Nevertheless, Italian authorities are still closely monitoring those they think might be involved in tax evasion. And with Dolce & Gabbana constantly putting their feet in their mouths about everything from in vitro fertilization to criticism of gay rights (despite the fact that both are gay), one wonders if they’ll trip up again and find themselves in further legal troubles.
11 Raj Rajaratnam
When J.M Rajaratnam sought a better life for him and his family, he relocated with them from their home of Colombo in Sri Lanka, a city and country increasingly plagued by violence and poverty, to the United Kingdom. Imagine how proud he would have been to see his son then take that opportunity and run with it, graduating from the Wharton School of Business at the University of Pennsylvania and founding the hedge fund Galleon Group. So successful was Raj Rajaratnam that he amassed a fortune of around $1.8 billion. Well, before you feel all warm and fuzzy inside, there is a slight catch. That being that Raj made his wealth by not entirely, 100% legal means. In 2011 he was found guilty of conspiracy and securities fraud and sentenced to eleven years in prison.
10 Robert Allen Stanford
There are three big numbers that sum up the life of Robert Allen Stanford. 2.2 billion, 7 billion, and 110. The first is an estimate of how much money he was worth, personally, at his height. The second is an estimate for how much money he defrauded his investors. The third is his prison sentence. 110 years. And he never even killed anybody and ate their face or anything. Stanford is an American former financier who ran the now defunct Stanford Financial Group. And by “ran”, I mean "used it to facilitate a great big Ponzi scheme", just like Ebbers and Madoff before him. Actually, they were all running financial scams at the same time, just Stanford was the last to be convicted for it, in 2012.
9 Chey Tae-won
Anybody who has been following the saga of President of the Republic of South Korea, Park Geun-hye, and her impeachment over her being unduly influenced by the daughter of a former cult leader, knows that South Korean corruption cases can be a little bit...different. Such is the case with Chey-Tae Won. Chey (also identified as Choi Tae-won) is the chairman of SK Group, a massive business conglomerate. His personal wealth has been estimated at around $3.5 billion. However, in 2013 Chey was convicted of embezzling nearly $50 million and sentenced to four years in prison. The swerve? He claimed he did so because of the influence of a supernatural power…OK. And one last twist: in 2015, Chey was pardoned by, you guessed it, the now impeached President Park.
8 Wong Kwong Yu (Huang Guanyu)
There’s a lot of confusion around Wong Kwong Yu. The first is his name. He is also known as Huang Guanyu. This appears to be less of an alias than just a difference in how one can transliterate his name from Chinese to English. His net worth is also disputed. The low estimate, from Forbes in 2005, has his worth listed as $1.55 billion. In 2008, the China Rich List, compiled by the Hurun Institute, valued him at $6.3 billion. Time Magazine had identified him as the richest man in China. What is for certain is where he is: prison. Wong is something of a rags to riches back to rags story. He is reported to have left school and his impoverished family at the age of 14, only to make himself a billionaire by his mid-30s, after winning a brutal boardroom battle for control over Gome Electrical Appliances. However, in 2010, Wong was imprisoned for insider trading, stock manipulation, and bribery. His 14-year sentence is seen by many as a warning to other overly ambitious businessmen in the ostensibly Communist People’s Republic of China.
7 Bernie Ecclestone
What is it with dudes named Bernie getting involved in white collar crime? Seems the only Bernie who isn’t, is the socialist Vermont Senator Bernie Sanders. Weird. Anyway, this entry doesn't quite satisfy our lust for schadenfreude, with Ecclestone never having actually been sentenced for a crime. However, the details of his case are too fascinating to omit. Ecclestone is best known as the chief executive of Formula 1, a position he only resigned in January of this year (though he is still heavily involved with the organization). The Brit’s personal worth varies significantly with estimates, but it’s fair to say he’s worth north of $3 billion. In 2014, a German court began proceedings to charge Ecclestone with bribery. He was accused of bribing a former German bank official, who himself was under investigation, $44 million to give up his stake in Formula 1. Instead of going to trial, however, Ecclestone simply paid the court a £60 million settlement. Let that sink in. He paid his way out of a bribery charge.
6 Silvio Berlusconi
Oh Silvio. Berlusconi is a former Italian Prime Minister, media tycoon, and until recently, the owner of the popular football club, AC Milan. Berlusconi’s personal wealth fluctuates with estimates, but according to Forbes in 2017, he’s worth $6.9 billion. And like most rich and corrupt tycoons/politicians, Berlusconi was found guilty of tax evasion. But not content with just that, Berlusconi also got done for having s*x with an underage prostitute. That’s different. While in office, Berlusconi became infamous for his “bunga, bunga” parties, and you don’t need to speak Italian to guess what that might mean. Berlusconi’s dalliances with the fabulously named “Ruby Rubacuori” (stage name) got him an initial sentence of seven years in prison, along with a conviction of abusing the powers of office. But the reptilian Berlusconi managed to slither his way to a successful appeal. However, the tax fraud charges stuck, but due to Berlusconi’s age (80) and a mountain of Italian bureaucracy, Berlusconi will get away with 1-4 years of community service, which he is currently serving, helping seniors with dementia.
5 Thomas Kwok
In 2005, Forbes estimated that Hong Kong realtor brothers Thomas and Raymond Kwok were worth $16.3 billion combined. That is a massive amount and you could be forgiven if you were suspicious of how they got it. The Kwok brothers were the co-chairmen of Sun Hung Kai Properties, the largest property developer in Hong Kong, a city that currently has the highest property rates in the entire world, by several estimates. The brothers were arrested in March 2012 and charged with bribery. They were accused of bribing Rafael Hui, the Chief Secretary of the Administration of Hong Kong. Raymond was cleared of all charges. Thomas was not so lucky. He was found guilty of conspiracy to commit misconduct in public office and sentenced to pay $500,000 and serve five years in prison. No word yet if he’ll be charged for that atrocious haircut.
4 Joseph Lau
Joseph Lau is a Hong Kong businessman, investor, and 61% owner of the investment holding company Chinese Estates holdings. According to Forbes, he is worth about $15 billion. He is also a convicted felon. Lau, along with business partner Steven Lo, was found guilty on March 14, 2014, of bribing a Macanese public works chief HK$20 million over the bid for land near Macau International Airport. However, despite both being autonomous regions of China, and Macau accepting Hong Kong dollars as currency (and also as bribes, apparently), the two do not have an extradition treaty, so Lau has not served any time. He is a fugitive, however, and were the 65-year old ever to go back to Macau, he would be arrested and put in prison.
3 Mikhail Khodorkovsky and Platon Lebedev
Mikhail Khodorkovsky was once considered the wealthiest man in Russia, worth an estimated $15 billion and ranked number 15 in the world. Like many Russian oligarchs, he was in the oil business, heading up Yukos Oil. In 2003, along with his business partner, Platon Lebedev, Khodorkovsky was imprisoned for fraud and tax evasion. They were convicted a second time in December 2010, of embezzling more than 200 million tons of oil and laundering the profits. It was this second trial that many saw as politically motivated; a case of Vladimir Putin trying to silence and lock away a critic and political foe. Amnesty International even took up Khodorkovsky's case and the man now sounded more like a political prisoner than a corrupt businessman. Khodorkovsky was eventually released in 2013 and was tacitly exiled from the country. In December 2015, a Russian court issued an international warrant for his arrest for the 1998 murder of Vladimir Petukhov, the mayor of Nefteyugansk, in a move that Khodorovsky and his supporters see as a sham. Lebedev has kept a lower profile since his release in 2014, staying in Russia and resuming his business career.
2 Pablo Escobar
Pablo Escobar, the infamous Colombian drug lord, was worth as much as $30 billion in the early 1990's. That would be about $55 billion as of 2016. That makes Escobar the wealthiest criminal in history. Escobar's Medellín cartel supplied as much as 80% of all cocaine entering the United States and in a single year turned over $21 billion. After the assassination of Presidential candidate Luis Carlos Galán, and the bombing of Avianca Flight 203, the public, which had at times supported him (he was even, briefly, an alternate member of Chamber of Representatives of Colombia in 1982), turned against Escobar, and the government pursued him. Escobar conceded to being confined to a luxurious prison of his own construction, La Catedral, in 1991. But he later escaped when he discovered the government was planning to relocate him to another prison. He lived the rest of his life as a fugitive before he was killed by police members of the Search Bloc in 1993, a day after his 44th birthday. His massive empire having dissipated or having been taken over by rival cartels. Crime definitely can pay, but it doesn’t often pay for very long.
1 Hosni Mubarak
Hosni Mubarak served as President of Egypt from 1981 to 2011, but was, in actuality, a dictator. During that time, Mubarak and his family amassed a mind-boggling fortune; as much as $70 billion, according to The Guardian. Mubarak scrounged up the obscene sum through corruption, bribery, and few legitimate business activities. Everything changed, though, with the Arab Spring, when Mubarak was forced to step down in March 2011 after weeks of protest. Mubarak was then detained and questioned about a litany of offences, but was eventually tried and convicted of negligence for failing to halt the killing of peaceful protesters during the revolution. He was initially sentenced to life in prison, but after years of appeals and commutations, Mubarak actually ended up being acquitted and released in March 2017. However, he had already spent years in prison and during that time suffered serious health crises (reported to be stomach cancer, heart problems, depression, and a broken leg) and the 88-year old is unlikely to ever fully recover.
Sources used: ABC, CNN, BBC, Emirates247