Billionaires Whose Money Couldn't Save Them From Serving Time

According to LuAnn De Lesseps, "Money Can't Buy You Class." And according to the billionaires on this list, money also can't buy freedom. We are living in a time where wealth and riches seem to hold the power to everything — except a "get out of jail free" card. We live in a world where greed takes hold of so many once they get a taste of what it's like to make more money than they ever dreamt of. Billionaires like Bernie Madoff and Elizabeth Holmes learned the hard way that money can't always stave off the consequences of immoral transgressions. If you break the law, you must face the music like everyone else. 

This narrative truly reveals the importance of accountability, no matter how much money you have. Madoff went from living in a $10 million Manhattan duplex apartment, jet-setting around the world and eating the finest of foods, to living in a jail cell, making $40 dollars a month cleaning other inmates' living quarters. Yikes. In a 2014 interview with Politico, he said, "I miss everything," noting that being estranged from his loved ones was the worst part of being jailed. "I don't have anything to live for."

In the eyes of the law, no amount of wealth can buy immunity from the consequences of one's actions — not even if you're a billionaire!

Viktor Bout, the notorious Russian arms dealer who was also known as "The Merchant of Death," was convicted on charges of terrorism and sentenced to 25 years in prison in 2011. Bout was said to be worth about $6 billion (money earned through his illegal activities) when he was arrested after providing AK-47s to terrorist organizations and cartels, and extradited to the U.S. "Viktor Bout in my eyes is one of the most dangerous men on the face of the Earth," Michael Braun, the former chief of operations for the U.S. Drug Enforcement Administration, told a correspondent for "60 Minutes."

Viktor Bout's luck changed in 2022 (and it had nothing to do with his money) when he became part of a prisoner swap discussion between the United State and Russia. WNBA player and U.S. citizen Brittney Griner was being held in Russia for having vape cartridges and cannabis oil. She'd been sentenced to nine years in prison. Additionally, Marine veteran and U.S. citizen Paul Whelan was serving 16 years for an alleged espionage charge. Secretary of State Antony Blinken submitted a proposal to Russia offering a prisoner swap. Bout would be released from incarceration for Griner and Whelan's release. Unfortunately for Whelan, he was not a part of the prisoner swap. In December of 2022, Griner was traded for Bout, and he was sent back to Russia. In July 2023, it was reported that he was running for political office.

Ding Yuxin is a Chinese billionaire and former chairwoman of Boyou Investment Management Corp who was sentenced to 20 years in prison for collusion in 2014, according to ChinaDaily.com. Ding reportedly bribed Liu Zhijun, China's former railways minister, with 49 million yuan (for two years between 2008-2010) "in exchange for lucrative contracts and connections" (per The New York Times) to help both of them get ahead, securing specific high profile business deals. It was reported by prosecutors that Ding's criminal activity included her illegally assisting over 22 companies in securing 57 railway projects which were valued at 185.8 billion yuan. She then gave illegal kickbacks to Liu and herself to the equivalent of $8 million to him, and $325 million to her. Ding started out as an egg-seller with very little education. Apparently, greed took over.

In addition to her 20-year prison sentence, she lost her own personal property worth over 20 million yuan, and was fined 2.5 billion yuan (the equivalent of $404 million). The former railways minister Liu was initially sentenced to death for bribery and abuse of power, although his sentence was suspended for two years. However, Liu's sentence was later commuted to life in prison. When it comes to the law, we're fairly certain that you don't want to break any in China.

Bernie Madoff – a name that likely triggers a lot of anger for so many. Madoff was an American financier/money manager and former chairman of NASDAQ. He was also the mastermind behind one of the most infamous Ponzi schemes in history. Madoff's financial fraud cost thousands of his investors billions of dollars and ruined so many lives (for some, it was their entire life's work and savings). His victims even included some very noteworthy individuals like Kevin Bacon and Steven Spielberg. Madoff's scheme came to light in 2008, sending shockwaves through the nation. He was charged and sentenced to 150 years in prison for money laundering and securities fraud. In 2009, he pleaded guilty to defrauding over 40,000 people. It was revealed that his shady ways began in the early 1970s, though Madoff himself claimed it didn't start until after the Gulf War in the '90s.

Following Madoff's conviction, a curse seemed to spread across his family. Both of Madoff's sons (who were involved in his illegal activities) passed away shortly after he went to prison. The eldest son Mark Madoff died by suicide in 2010, and youngest son Andrew died of cancer in 2014. In 2022, Madoff's sister Sondra Wiener and her husband were found dead in their Florida home as an apparent murder-suicide. Bernie Madoff died in prison at age 82 on April 14, 2021 of natural causes.

Sir Allen Stanford (he was knighted in Antigua) is a billionaire known for orchestrating one of the most significant Ponzi schemes in history, after the Madoff scandal. Born in Texas, Stanford was the chairman of the Stanford Financial Group, a financial services company that operated out of Antigua. Stanford grew up middle-class and became an insurance salesman who worked his way up to becoming an investment and money manager. He founded SFG in 1991. SFG boasted over $50 billion in management and was the biggest employer in Antigua. Allen Stanford was known as one of the richest men in the United States.

First charged in 2009, Allen Stanford was convicted in 2012 of selling fraudulent certificates of deposits from his offshore bank (about $7 billion worth), where most of his clients to this day have not recouped their losses. Stanford was stripped of his knighthood and sentenced to 110 years in a Florida prison without the possibility of parole. In an interview with the BBC, Stanford maintains his innocence. "I am in this situation caused by the wrongful actions of the U.S. government and particularly the SEC. There is no question that I was a scapegoat for what happened in 2008 and 2009, post-Madoff ... They needed a head on a block." Additionally, Stanford has been outspoken about his poor treatment in prison.

Wong Kwong Yu is yet another Chinese billionaire and entrepreneur who once held a prominent position in the business world, particularly in the electronics sector, who wound up behind bars. Unfortunately, greed got the best of him as he served time for insider trading and corporate bribery. Wong rose to power as the founder and former chairman of GOME Electrical Appliances Holdings, which became China's largest privately owned electronic retail chain (think Best Buy but larger). He started as a young entrepreneur selling various electronic appliances in Beijing during the early '90s. He launched his company GOME in 1987 after realizing that China didn't have any type of "retail giant" for home appliances and electronics. In 2006, he made the Forbes Rich list with a net worth of 18.1 billion yuan. Wong was officially the richest man in China.

The company went public in 2004. By 2008, Wong's legal troubles began when rumors circulated of alleged stock price manipulation and insider trading. These rumors turned out to be true and ultimately led to his arrest and conviction. Wong Kwong Yu was convicted in 2010 and sentenced to 14 years in prison for insider trading and bribery. He was released from prison in 2020 on parole after serving 10 years. It was reported by the local media that during his time in prison, he continued to communicate with GOME employees, offering business ideas and suggestions.

Marco Muzzo, a Canadian billionaire whose family was well-known for their success in the construction and real estate industry (they founded The Muzzo Group), gained some very negative media attention for his prominent family due to a tragic incident in 2015. Muzzo was involved in a horrific car accident that resulted in the deaths of three children and their grandfather. Muzzo was drunk and too incapacitated to drive (it was reported he was three times over the legal limit). It was reported that after getting off a flight from Miami, where he'd been celebrating his bachelor party, Muzzo ran a stop sign and crashed into the family's van. Muzzo pleaded guilty to multiple charges, including impaired driving causing death. He was sentenced to 10 years in prison.

Muzzo appeared to be remorseful in court and to the family, which worked well for him. In 2020, he was granted full parole and released from prison. The mother of the three youngsters who perished in the car crash, Jennifer Lake, however, was unhappy about the parole. "I am angry that my children never got the chance to grow up. It's scary when you want a hug from your children and they aren't there. Please do not give this drunk driver anymore privilege than he already has," she said in a victim impact statement (per CTV News). Sadly, later in 2015, the father of the three children, Ed Lake, died by an apparent suicide.

Oil tycoon Eike Batista was once known for being Brazil's wealthiest man. Now the charismatic and confident former billionaire is serving 30 years in prison for money laundering, bribery, and insider trading. Batista is the son of a mining executive and founded the EBX Group (a conglomerate of oil and mining companies) in 1980. The group focused on oil and gas, mining, shipping, energy, and more. EBX seemed to take off and garner success early on, experiencing rapid growth and attracting significant investments. Batista generated substantial wealth for himself and the company. He was added to the Forbes list of billionaires by 2008. Despite his initial success, many of Batista's ventures faced financial challenges after the price of petroleum dropped, and the promised returns did not materialize to his investors or EBX. He failed to pay off the debts he accrued when previously expanding his oil production, and his entire business began to fall apart. Batista seemingly was desperate to save it — even if that meant illegal activity.

In 2014, Batista was set to go to trial for insider trading, when a judge for the trial was spotted driving one of Batista's expensive cars while out and about. The trial was postponed, and Batista was then accused of bribery. By 2018, he had been tried and convicted of bribing the former governor, Sergio Cabal (now also in prison), with over $16 million and sentenced to 30 years in prison.

Joaquín "El Chapo" Guzmán is one of the most notorious Mexican drug lords of this generation. Guzmán rose to power as the leader of the Sinaloa drug cartel, one of the most powerful and dangerous criminal organizations in the world (which he founded and named after his home state). Guzmán may be the most infamous figure in the seedy underworld of drugs and cartels. He began his criminal career in the 1980s, rising up the ranks of the drug trade in Mexico. He initially worked for the Guadalajara cartel and had a leadership role early on, focusing on smuggling cocaine into America. Guzmán formed the the Sinaloa cartel after the Guadalajara cartel dissolved. Sinaloa became the most powerful drug trafficking organization in the world, controlling a significant share of the drug trade in the United States.

El Chapo was captured by law enforcement many times but continually escaped. In 1993, he was captured in Guatemala but managed to escape from prison in 2001. He remained a fugitive for more than a decade until his capture in 2014. However, he escaped again in 2015 but was recaptured in 2016. He stood trial in 2018, and in February 2019, he was found guilty on all counts of drug trafficking and money laundering. In July 2019, he was sentenced to life in prison without the possibility of parole.

Canadian-born Chinese billionaire Xiao Jianhua was notoriously removed from the Four Seasons hotel in Hong Kong in 2017, after being arrested for embezzlement and bribery. Xiao is the founder of Tomorrow Holdings, a prominent Chinese umbrella company with a focus on various industries: banking, real estate, and healthcare. Tomorrow Holdings and Xiao have been involved in investments and acquisitions with some of China's leading financial companies, which allowed them to play a big role in the country's financial landscape in the early to mid-2000s. By 2016, Jianhua had a net worth of almost $6 billion, but his world was about to fall apart.

In 2017, Xiao was charged with "illegally siphoning away public deposits, betraying the use of entrusted property, and the illegal use of funds and bribery," according to NBC News. This was why he was seen being forcibly removed from the Four Seasons hotel in 2017, and he wasn't seen in public until his 2020 court date. He was sentenced to 13 years in prison, and Tomorrow Holdings was fined 55 billion yuan. It was revealed that starting in 2001, he gave shares (real estate, cash, and other assets) to government officials as bribes in order to benefit himself and the company. Xiao admitted to all of his crimes and appeared to be remorseful, which helped his case and sentencing in court.

The late Alfred Taubman was a billionaire businessman and philanthropist, best known for his role as the passionate and brilliant CEO of Sotheby's, the famous auction house. Taubman had significant involvement in the real estate industry, which is how he initially rose to success and made his fortune. He began his career as a real estate developer in Michigan. He built shopping centers and strip malls to fulfill the American people's desire to shop. By the 1980s, Alfred Taubman became heavily involved with Sotheby's. He acquired a significant stake in the company and later became its chairman and CEO, respected by many. During his time with Sotheby's, he played a crucial role in modernizing and expanding the operations of the renowned auction house. The New York Times noted that Taubman "turned a sleepy Sotheby's auction house into a global power of art sales."

In the early 2000s, Taubman was embroiled in a very high-profile price-fixing scandal involving Christie's, a competing auction house (Taubman vehemently denied his involvement, however). He was accused of conspiring with Christie's chairman, Sir Anthony Tennant, in London to fix commission fees. Taubman was convicted in 2002 and served nine months in jail. He also gave up his portion of ownership of Sotheby's. He continued to shop for all his personal art at Sotheby's for the next decade of his life until he died in 2015.

Silvio Berlusconi is the former prime minister of Italy, who was also a fierce billionaire businessman and politician. The late Berlusconi is also known for being equally controversial as well as influential in Italian politics and society. He built the largest media conglomerate in Italy, Mediaset, in the 1980s and even bought an Italian soccer team before becoming involved with politics and starting the center-right party, Forza Italia! (formed in 1994). He lost the next few elections after his success in 1994, but returned to office from 2001-2006, with his political views leaning toward conservative economic policies and reform.

Over the progression of his career, Berlusconi faced quite a few legal battles, including being convicted for bribing a senator and committing tax fraud. It was reported that he even had 10 cases against him — dropped (in addition to at least 10 acquittals). In 2010, he was accused of abuse of office and paying for sex with a minor at a nightclub. The year 2011 would mark the end of Berlusconi in office, and by 2013 he would be found guilty of paying for sex with a minor and sentenced to seven years in jail. Berlusconi was acquitted in 2015 by an appeals court that stated there wasn't any proof that he knew the young woman was underage. Silvio Berlusconi died in June of 2023 at the age of 86.

Elizabeth Holmes was once hailed as the next Steve Jobs. After dropping out of Stanford University at the age of 19, she founded Theranos, a health technology company, in 2003. Holmes claimed that Theranos had developed a revolutionary blood-testing technology that could run an array of tests with only a few drops of blood. This garnered Holmes and Theranos attention and investments from high-profile people. At its peak, the company was valued at $9 billion, and Holmes was known as the world's youngest female self-made billionaire.

However, the dream was about to die. It was revealed that Theranos technology didn't work as claimed, and the company was misleading investors and patients. In March 2018, the U.S. Securities and Exchange Commission charged Holmes and ex-boyfriend Ramesh "Sunny" Balwani (also former Theranos president) with 11 counts of fraud. The SEC alleged they had raised more than $700 million from investors through an elaborate, years-long scheme. In 2022, Holmes was found guilty on four counts of investor fraud and conspiracy and sentenced to 11 years in prison. According to The New York Times, Holmes took the stand at her trial and appeared to go back and forth in taking responsibility for her actions, and in shifting the blame to others.

"At so many of the forks in the road, she chose the dishonest path," assistant U.S. attorney John Bostic said at her trial.