It would come as no surprise to many a mortal man and woman that people don’t get rich by getting lucky. Many of them earn it, and they earn it in a variety of ways. They are able to earn massive amounts of money by using their high levels of education, extraordinary connections, and only a touch of good luck. We would love to think things were always done by hard work, but there are a lot of other variables that are involved in success. One is the age-old silver spooners — you know, “those” wealthy people who feel like they’re entitled to wealth because their ancestors had money. Then there are those who are just dirty; they make money in a variety of illegal ways. These are the criminals of the world who make money off the backs of the hardworking poor and middle-class folks. Then it becomes abundantly clear how they make all their money.
Quite a few people assume that it’s just white collar criminals, wealthy jerks, who cheat people and commit to criminal activities in order to pad their pockets. But there are also celebrities who have gotten into trouble by making poor choices and breaking the law. And when you get caught breaking the law, you pretty much can guarantee that jail may not be too far behind. A lot of times, people expect that these wealthy individuals can get out of anything, but sometimes, that just isn’t true. These are 15 Shady Millionaires Who Made A Lot Of Money And Went To Jail.
15. Dolce and Gabbana – Tax Evasion
Fashion is big in the world, and Dolce and Gabbana are big time players in the business. In 1985, D&B made their debut at Milano Collezioni’s Nuovi Talenti. This “new talent” venue was perfect for D&B to get instant recognition. Since then, the company has enjoyed success and is worth over $1.5 billion. But all wasn’t rosy for the company. Taxes, taxes, and more taxes — the company was doing its best to avoid paying taxes. The Italian government was not amused and as times have gotten tight in Europe, they opted to crack down on those who were attempting to avoid paying their fair share. D&B came up on their radar. Stefano Gabbana and Domenico Dolce were both arrested on tax evasion charges. They ended up getting a 20-month suspended sentence and a whopping $1-billion charge in taxes and fees. They had set up a fictitious company to help shield them from their tax liabilities, using it as a false write-off for years. The government caught up with them. They have been back and forth with the Italian courts that have changed their minds on their guilt depending on who was being paid off and when.
14. Silvio Berlusconi – Sex And Taxes
Silvio Berlusconi was the former Prime Minister of Italy. Silvio was a favorite of voters, being a four-term PM for his country. However, his success was not exactly scandal-free. For years Silvio had a myriad of issues during his tenure. He had numerous run-ins and accusations that never quite stuck to him. He was hit with many sex scandals during his time in office, all of which seemed to just roll off of him. But in 2013, things seemed to catch up with Silvio. He got caught in a tax scandal he couldn’t deny or talk his way out of. He was hit with a 4-year sentence which was ultimately reduced to 1 year. Silvio ended up doing unpaid community service to pay back his time. The charges and arrest were an embarrassing end to an otherwise tumultuous tenure.
13. Heidi Fleiss – Call Girl Service
Well, hello, madame! Heidi Fleiss was a highly successful businesswoman at her height. She amassed millions in profits from her business — her sex business that is, and business was good! We all remember Charlie Sheen getting dragged into this mess. He was a witness against Heidi Fleiss because he was one of the many public figures who used Fleiss’s high-priced high-end call-girl services. Now, Fleiss certainly got nailed for running the prostitution ring, but she got additional time for tax evasion and money laundering. All the charges stemmed from her illegal business activities and got her 37 months in prison. Her notorious black book has many names enclosed inside of it that would blow up wealthy businessmen as well as Hollywood’s elite. A person claiming to have numerous pages of the book attempted to sell it online. Names leaked that were inside the book include Johnny Depp, Star Wars creator George Lucas, Hugh Hefner, Jack Nicholson, Billy Idol, OJ Simpson, Robert Shapiro (famous defense attorney), and numerous others referred to by coded entries.
12. Bar Refaeli – Tax Evasion
Apparently, being hot can get you in and out of almost any situation, except when you decide not to pay taxes. Back in December 2015, Bar Refaeli‘s home was raided by the Israeli authorities due to suspicions over tax evasion. The supermodel and her mother were targeted for lying about where they lived and all those expensive properties and cars, which were “gifted” to her. They used residency as the catalyst for avoiding paying taxes due to her homeland rules. In addition to avoiding paying taxes for income in the millions, Refaeli was also accused of accepting various perks, which included apartments and cars that were stashed in other family members’ names, her mother and brother being two of them. Refaeli was regularly photographed in a Range Rover and Lexus she claimed to be given to other family members and not her. The whole spectacle was clear as day to many despite Refaeli trying to get out of trouble. The investigation has spanned over a year and continues to be a high-stakes pissing contest between the supermodel and her home country.
11. Russian Oil Tycoon Gets Pinched For Money Laundering
Besides having one of the most complicated names on the list, Vladimir was one of the most successful businessmen in all of Russia. Vladimir learned long ago that cutting corners would help him amass a massive financial empire. He was able to do so to the tune of around $10 billion. He was the head of one of Russia’s most successful oil companies. In 2014, even a corrupt country like Russia proved that they had their limits. The Russian authorities nailed Vladimir for money laundering, and clearly, the Russian billionaire failed to pay off the right people. He had his company and all his assets stripped away from him. Ironically, the entire oil industry, and especially Russia’s oil industry, has taken a sharp downturn since. Perhaps things worked out best for him in the end. Vladimir was put under house arrest, and eventually, he paid a fine of $1.1 billion and was magically absolved shortly thereafter.
10. Wesley Snipes – Tax Evasion
Let’s go straight to Mr. 1990s, Wesley Snipes, and dive down into some of his issues. It’s very rare that you see a celebrity the likes of Wesley Snipes (and he was pretty darn big) going down in court and actually having to serve time for his financial transgressions. But Snipes set out to cheat the system to the tune of millions, and Uncle Sam wasn’t about to let him walk without letting him take a hit to his pocketbook to go along with his lost freedom. It was April 24, 2008, when Johnny-Law finally caught up with Snipes. The actor was sentenced to 3 years in prison while his money manager got 10 years for falsifying tax returns and tax amendments in order to collect more cash from Uncle Sam. Snipes tried to get out of his issues and appealed to the Supreme Court but was ultimately denied and had to serve his time for falsifying millions in earnings.
9. Jim Irsay – DWI
If you’re an American football fan, then you know all-too-well about the NFL. The biggest sports entity in the United States is flush with cash, the numerous owners being the biggest beneficiaries of the league’s success. Because he was worth over $1.7 billion, you would be surprised to know that this NFL owner got arrested. The reasons were a little more understandable but not acceptable. Irsay‘s long-time girlfriend had just passed away 9 days prior. The wealthy man was understandably upset and was drinking heavily. He was driving erratically and was pulled over by the police. The police found numerous prescription pills in the car. He was given a 60-day suspended sentence, and the NFL slapped him with a $500,000 fine.
8. Richest Man in China – Stock Manipulation
Not only does Wong Kwong Yu have a name that rhymes; he’s also quite the businessman. In 2006, he was the richest man in China. A former high school dropout, Wong made his fortune in retail electronics. The Chinese authorities started to pay close attention to Wong as he racked up a ton of money. He exceeded $1.5 billion in net worth, and everyone was noticing his exploits. Wong may have sold TVs and other electronics, but he made a lot more money manipulating stock prices. Wong got into the stock manipulation game, and the Chinese government was none-too-amused. They caught Wong making six-figure deals on illegal insider trading and had him dead to rights. Then, they caught Wong trying to pay off the courts with a $750,000 bribe to avoid jail time. Ouch. He got the book thrown at him with a 14-year prison sentence due to bribery, stock manipulation, and insider trading.
7. Martha Stewart Double Dips – Insider Trading
Martha Stewart is known for a lot of things. She has been a highly successful businesswoman. With a net worth well over $600 million, she has built a business empire. In addition to not fully complying with tax laws in New York and getting a firm slap on the wrist, Stewart ran into hot water when it was discovered that she was involved in trading stocks on illegal inside tips. She was convicted of insider trading with regard to shares of ImClone Systems, proving yet again, that the rich cannot help themselves from their own greed. Martha Stewart, her broker at Merrill Lynch, Peter Bacanovic, and ImClone’s CEO, Samuel D. Waksal, were all convicted for illegal trade activities. Martha got five months in prison and five months of home confinement. She has emerged stronger than ever, but the world felt as though her empire would be swallowed whole. Instead, she has become a better-known commodity after serving jail time, appearing in MTV programming and Comedy Central Roasts in comical and personable manners.
6. Lauryn Hill – Tax Evasion
The sultry and sexy singer of the Fugees, Lauryn Hill, wowed audiences across the world with her beauty and vocal abilities. Although the Fugees are no more, this 8-time Grammy winner got three months in Federal prison when she avoided paying taxes from 2005-2007. Hill dipped out on her tax responsibilities and opted to not pay taxes on more than $1.5 million in money she brought in. She blames her tax evasion on dropping out of the music business. So if you translate that to a normal human being, if you switch jobs, you don’t have to pay taxes on that severance package you get? Yeah, not so much Lauryn. And she rightfully got smacked by the law. Ironically, right after serving out her prison sentence, she jumped right back into the music business with a hyped-up post-prison show.
5. Michael Milken – The Junk Bond King Commits Securities Fraud, Fined $600 Million
Michael Milken may not be known to many, but back in the late 1980s, a heck of a lot of people knew exactly who he was. Known as the “Junk Bond King,” Milken was one of the pioneers of buying and selling garbage. Long before the housing crisis swallowed the world whole, Milken was digging into the many issues surrounding junk bonds, and he would buy and sell very low-rated corporate debt. Milken had inside info on everything he was doing, which enabled him to use corporate takeover plays with the inside info. His manipulations made him millions upon millions. He settled with authorities by pleading guilty to securities fraud and paid out a whopping $600-million fine. He was banned from the entire securities market for his actions. He received a sentence of 10 years for racketeering and securities fraud but got it down to 2 years. He still has a $2.5-billion net worth by the way, so they didn’t exactly cripple him. And on a very interesting side note, I personally went to the same high school as him, Birmingham High School in Van Nuys, California (during different decades of course). Milken donated a state-of-the-art football field and track to his former high school way back in the day. (Thanks, Mike!)
4. Hedge Fund Manage Commits Securities Fraud, Fined $150 Million
Raj Rajaratnam has a net worth of nearly $2 billion and was one of the many crooks to roll the streets of New York in a stretch limousine. He was the former hedge fund manager for the Galleon Group, a New-York-based hedge fund management firm. Naturally, Rajaratnam was nabbed for securities fraud. We’re all going to pretend that every hedge fund manager and his team don’t get involved in insider trading, (wink-wink) but Rajaratnam’s issues were so egregious that it got the cuffs slapped on his wrists. He lost in court and was given an 11-year sentence and fined $150 million for his illegal activities. His hedge fund peaked at $7 billion back in 2008 before he got arrested in 2009, and his empire crumbled to ashes.
3. Andre Esteves – Insider Trading
Andre Esteves is one of Brazil’s biggest crooks. He is also one of their richest. He is known for two things in Brazil: being one of the richest men in his homeland and doing as many financially illegal things as possible. Esteves was the CEO of BTG Pactual. This was a multinational investment bank that had their fingers all over the world. Make no mistake about it: Esteves was as dirty as they came. In addition to being a prominent Brazilian senator, Esteves was arrested due to his massive financial conspiracy and numerous accusations of insider trading. He ran an oil company, and although he was arrested, the highly corrupt Brazilian courts couldn’t follow through on his crimes, and Esteves went from winning house arrest to, more recently, being released outright. One of the wealthiest men in all of Brazil was all smiles after his release by the Brazilian Supreme Court.
2. Bernie Ebbers – Robbed Investors Of Billions Of Dollars
Bernard John Ebbers is an infamous name in financial circles. He’s one of the most notorious financial figures in American lore. At his peak in 1999, Ebbers amassed a fortune of over $1.4 billion at its height. But much like a lot of shysters out there, Ebbers’ ability to push the envelope with financial rules and regulations were evident as he committed numerous financial crimes. The Canadian-born Ebbers rose to power and prominence as founder of WorldCom. The enormous telecommunications company thrived, and Ebbers was named chief executive of the year two times over. Ebbers was named one of the 25 most powerful people in the world by Network World. But Ebbers used WorldCom and its stock as his own private piggy bank. And when a failed takeover attempt of Sprint took place in 1999, it would prove to be the beginning of the end for Ebbers. He was responsible for falsifying financial records and statements. He got the book thrown at him for costing thousands upon thousands of investors billions of dollars. He received a 25-year sentence for his offenses and is serving it out in a minimum security prison.
1. Bernie Madoff – 150 Years for Ponzi Scheme
Prior to Bernie Madoff‘s fallout on December 11, 2008, WorldCom’s demise and Bernie Ebbers’s criminal activities were some of the worst committed in the United States. But records are made to be broken, and that’s where Bernie Madoff comes into play. Madoff received a legendary sentence of 150 years for his crimes, which the judge and many in his case have called “unprecedented.” The Ponzi scheme, as admitted to by Madoff, involved him depositing money into an account and leaving it there and then falsifying investment claims with the ability to backdate stock transactions and lie about larger-than-normal returns. (Now that’s a mouthful!) Many in the business were weary of Madoff’s company and his issues to the point that other financial institutions wouldn’t do business with him. When clients wanted their money pulled out, Madoff would pay them from the account where he held their money that he had never invested. He would steal from “Peter to pay Paul” in this scenario, and the last ones in were often the ones who got hurt the most. Madoff defrauded his clients of a whopping $65 billion. There is quite a bit more to the story that will never be uncovered, but it’s clear that Madoff was one of the biggest scammers in all of history, stealing money from Jewish organizations, friends, the Central Bank of Ireland, and anyone and everyone without regard for them. He is the Satan of the financial world.