Money can be a cruel mistress. While it can bring about real positive change, it can also drive some normally good people to do some pretty nasty things. Wall Street, in particular, is full of various “villains” trying to game the system and break the rules. From fraud and Ponzi schemes to stealing and money laundering, Wall Street has done it all. While the names may be different, but the outcomes are generally the same.
And when the perpetrators of Wall Street’s crimes get caught, it can make for a great story. Here we profile the 15 biggest crooks that have managed to shake up the world of finance over the years.
Be sure to also read A Brief History of Mutual Funds
1. Michael Milken
The Crime: Former Drexel Burnham Lambert bond trading superstar Michael Milken deserves a place in the Wall Street Hall of Fame as the man who basically created junk or high-yield bonds during the 1980s. Before this time, companies that didn’t have the best credit were almost shut out of the capital raising environment. Milken changed that and set forth the leverage buy-out binge of the 1980s and set-up systems that are still in place today.
However, it seems that all that power and knowledge of LBOs went to Milken’s head.
It all went sour for Milken when a federal grand jury indicted Milken on 98 counts of racketeering and fraud. The cause of these issues was that Milken was involved in a large insider trading investigation. As his plea bargain, investment banker Ivan Boesky implicated Milken on several illegal transactions – including insider trading, stock manipulation, fraud and buying stocks for the benefit of another person. This was the first time that the RICO act was used against someone that wasn’t officially involved in organized crime.
The Punishment: In 1990, Milken pleaded guilty to six counts of securities and tax violations. His sentence included paying out roughly $1.1 billion in fines to the SEC, Drexel investors and court fines, as well as receiving a lifetime ban from any involvement in the securities industry. Milken also served two years in jail.
2. Barry Minkow
The Crime: It seems that for Barry Minkow, the very beginning of his empire was created using some unscrupulous means. While in high school, Minkow founded ZZZZ Best, which was a successful carpet-cleaning and restoration company. At least on the surface, it was. In the beginning, to meet the meet basic expenses of ZZZZ Best, Minkow used check kiting, stealing, staging break-ins at his offices, and running up fraudulent credit card charges to find capital.
Later, in order to grow ZZZZ Best, Minkow got into the “insurance restoration” business and created a series of fake documents, even going so far as rent offices to create the illusion of actual carpet cleaning work. Banks gave capital to ZZZZ Best, which Minkow used for his own gains. After taking the company public, the Ponzi Scheme began to unravel. By the time Minkow was caught, investigators estimated that roughly 90% of ZZZZ Best’s revenue was faked in some matter.
The Punishment: In January of 1988 Minkow was brought in on 54 counts of racketeering, securities fraud, money laundering, embezzlement, mail fraud, tax evasion and bank fraud. He was found guilty on all charges and sentenced to 25 years in prison. After Minkow’s early release from prison in 1995, he continued his dubious ways and was recently convicted of insider trading and mail fraud.
3. Jordan Belfort
The Crime: After dropping out of dental school, Jordan Belfort started his career as a stockbroker at L.F. Rothschild. It was there he developed a taste for the lavish and fast lifestyle. He went on to found the brokerage firm Stratton Oakmont. At Stratton, Belfort really began his dubious career in the securities industry.
Stratton was considered a “boiler room” firm that marketed penny stocks and other illiquid securities. Investigators alleged that Belfort and other brokers at Stratton engaged in various “pump and dump” schemes designed to defraud new investors while enriching older ones. The films “Boiler Room” and “The Wolf of Wall Street” were based on the exploits of Belfort and Stratton Oakmont.
The Punishment: In 1998, Stratton Oakmont was shut down by regulators and Belfort was indicted for securities fraud and money laundering. After cooperating with the FBI, Belfort served 22 months in federal prison. He was also required to pay nearly $110.4 million in fines and fees.
4. Bernard Madoff
The Crime: Bernie Madoff began his working career actually as a lifeguard and sprinkler installer. Taking the money he saved from those ventures as well as a $50,000 loan, Madoff started Bernard L. Madoff Investment Securities LLC in 1960. Originally, the firm was designed to trade penny stocks, and Madoff eventually became one of the biggest market makers on Wall Street. In fact, some of the technology invented and popularized by Madoff became the NASDAQ stock market.
Madoff would also delve into asset management. Dubbed the “Jewish Bond,” Madoff’s various hedge funds were known for consistently making above average gains, year in and year out. Unfortunately, even the best traders have down years and several investigators began to get curious about Madoff’s continued success.
After Madoff had trouble with a large series of redemptions from investors, it came to light that the asset management business of Bernard L. Madoff Investment Securities was “one big lie” and had been a huge Ponzi scheme – one that involved upwards of $65 billion at first record.
The Punishment: For conducting the largest and longest running Ponzi scheme in history, Madoff was hit with a huge sentence. In 2009, Madoff pled guilty to 11 federal felonies, which included securities fraud, money laundering, perjury, theft from an employee benefit plan, and making false filings with the SEC. For this, he was given a 150-year prison sentence.
5. Raj Rajaratnam
The Crime: Sri Lankan born hedge fund manager Raj Rajaratnam’s story starts out normal enough: he began his career as a loan officer at Chase. It was here that focused on the technology sector. He later worked as tech stock analysts at Needham & Co. After excelling in the role, he started a hedge fund named Galleon Group.
At its peak, Galleon’s main fund had nearly $7 billion and returned an average of 22% a year. Yet, those returns came at the expense of insider trading. Raj Rajaratnam used connections over the years—such as his friend McKinsey & Company’s Rajat Gupta—to secure information about various tech stocks and their dealings. Rajaratnam would buy or sell the stocks ahead of the news becoming public.
Those insider trades helped boost the value of his various hedge funds by about $60 million. According to the Justice department, that makes it the largest hedge fund insider trading case in United States history.
The Punishment: In 2011, Rajaratnam was found guilty on 14 counts of securities fraud and was sentenced to 11 years in prison. This prison sentence was the longest ever handed out for insider trading.
6. Hiromasa Ezoe
The Crime: Hiromasa Ezoe may not be a household name here in America, but the Japanese businessman was at the center of one of biggest bribery and insider trading deals in the world. Ezoe wasn’t a Wall Streeter; he founded advertising company Recruit back in 1960. Recruit was originally a job information magazine for students, but quickly expanded into other magazines and job-listings for professionals.
The scandal, and ultimately Ezoe’s downfall, was that the businessman, in exchange for political favors, gave shares of Recruit spin-off Cosmos to various Japanese politicians before it went public. After the IPO, shares surged and the politicians made an estimated ¥66 million each on the opening day. The scandal involved not only Ezoe, but the former and current prime minister, several cabinet members and 30 other leaders in the Japanese government.
The Punishment: Despite being arrested in 1989, Ezoe’s trial took 13 years and over 300 court appearances to complete. In 2003, he was sentenced to three years in prison, which was suspended; he actually served no time for the Recruit Scandal.
7. Andrew Fastow
The Crime: Andrew Fastow started his career trading asset-backed securities at Continental Illinois. This firm would eventually become the second largest bank to fail in the U.S. However, his work at a little firm named Enron would be the reason why Fastow became truly famous.
As CFO, Fastow created the web of shell companies and partnerships that Enron owned and did business with. These companies provided the energy firm with seed capital, and also enabled it to hide massive losses and debts. The special purpose entities allowed Enron to appear debt-free, while the firm really had about $30 billion in debt outstanding. Fastow also had a stake in several of these funds, providing him with hefty management fees.
When Enron’s debts became too massive to hide, the firm declared bankruptcy and Fastow’s web of depiction was reviled. Enron became the worst accounting fraud in U.S. history.
The Punishment: In 2002, Fastow was charged with 78 different counts of fraud, money laundering, and conspiracy. However, his work as an informant on other Enron employees helped him receive a reduced sentence of 6 years.
8. Dennis Kozlowski
The Crime: There’s plenty of debate on whether or not Dennis Kozlowski was actually really guilty of his crimes. Kozlowski joined Tyco in 1975 and eventually became its CEO in 1992. After a series of mega-mergers and buy-outs, the firm became one of the biggest conglomerates in the world, with assets spanning a multitude of industrial products. Kozlowski helped guide the firm to consistently beat Wall Street’s expectations and earnings. This earned Kozlowski a big pay day.
This is where his troubles began.
Kozlowski had one of the most complicated pay packages of any CEO. Perhaps too complicated. Insiders alleged that Kozlowski had been stealing from the firm to pay for his lavish lifestyle and that these expenses were not approved by shareholders. These expenses included roughly $81 million in bonuses and $14 million for art for his apartment, which was purchased by Tyco.
The Punishment: After two trials, prosecutors were able to convict Kozlowski on crimes related to the bonuses and reported theft at Tyco. The former CEO was sentenced to a minimum of 8 years and 4 months and a maximum sentence of 25 years. Kozlowski was initially denied parole, but was set free in 2014.
9. Anthony Elgindy
The Crime: Anthony Elgindy rose to prominence in the late 1990s as a famed internet chat room poster. He later used that fame to start a private paid chat and internet stock site focused on shorting small-cap stocks. He would later found Pacific Equity Investigations – a short seller/trading organization as well as Key West Securities.
Elgindy’s first brush with the law came in 2003 when the NASD ruled that Elgindy and his firm Key West Securities "engaged in a manipulative scheme” to drive down the price of a stock. He was fined $51,000 for fraud. Elgindy’s big push came when he obtained several pieces of information from former FBI agents on several small-cap stocks. He used that info to manipulate the price of 32 different stocks.
The Punishment: Since he had stolen FBI information, Elgindy’s punishment was severe. His conviction of securities fraud, extortion and obstruction of justice came with an 11 year prison sentence and $1.5 million worth of fines.
10. Tang Wanxin
The Crime: Tang Wanxin and his brother started off as simple tomato farmers in China. However, they would turn their simple tomato farming operations into one of the largest companies in China. By 2004, D’Long International owned and had invested in hundreds of industrial and financial services operations.
To finance these operations and buy-outs, Tang used some illicit means. Beijing brought charges against Tang and various managers at D’Long with illegally raising $5.6 billion from the public between 2001 and 2004. The charges implicated more than 2,500 organizations and 32,000 individuals.
The Punishment: Tang was found guilty in a swift trial and was sentenced to 8 years in prison. Though he was once one of the richest tycoons in China, Tang had his personal assets seized.
11. Bernard Ebbers
The Crime: Bernard Ebbers built WorldCom into one of the largest telecommunications firms through acquisitions and the cleverly timed purchase of MFS Communications and its internet protocol systems. It would later buy MCI Communications. This acquisition earned him plenty of accolades as well as a huge salary. However, despite building one of the biggest telecoms in the world, Ebbers’ empire began to crumble when it came to light that not everything was kosher at WorldCom.
Ebbers helped orchestrate massive accounting fraud at WorldCom to the tune of $11 billion. The fraud included booking line items and entries designed to inflate revenue. WorldCom would file for bankruptcy due to the strain of the charges and debt.
The Punishment: Despite denying the allegations, Ebbers was charged with nine counts of securities fraud and other felonies. He was sentenced to 25 years in minimum security prison and was forced to pay out nearly $6 billion in restitution to former WorldCom shareholders.
12. John J. Rigas
The Crime: Before Comcast was the dominant cable provider, Adelphia was the biggest giant in town. It was here that founder John Rigas made his fortune. Starting out small, Rigas used Adelphia as a vehicle to make acquisitions, and eventually the firm became the dominant cable company in nearly 30 states.
Despite earning a massive salary as founder and owning the vast bulk of shares, Rigas and other family insiders began to loot the company’s coffers. The family used various off-sheet special purpose vehicles—similar to Enron and WorldCom—to pull in over $100 million for themselves, as well as concealing nearly $2.3 billion in debt. Once this became known, Adelphia was forced to file for bankruptcy and was purchased by Comcast for peanuts.
The Punishment: Rigas—along with his two sons—was charged with the trio of bank fraud, wire fraud, and securities fraud. He was sentenced to 15 years in federal prison. In addition, Rigas was stripped of his ownership of the NHL’s Buffalo Sabers hockey franchise and was basically left penniless to pay the various legal fees and fines.
13. Samuel D. Waksal
The Crime: It seems that ethics weren’t necessarily on the top of Sam Waksal’s mind throughout his career. After earning his doctorate, his next 15 years as a medical researcher were plagued with problems – such as misrepresenting the source of material and fabricating lab results. After these missteps in academia, Waksal founded the biotech firm ImClone.
ImClone’s cancer antibody drug Erbitux had the potential to be a huge blockbuster. As such, shares of the stock surged. Unfortunately, the FDA rejected the drug. Before it was announced that Erbitux failed clinical trials, Waksal began selling his shares – a lot of them. As did his family and friends, including Martha Stewart. Waksal and crew committed a textbook case of insider trading.
During the investigation on Waksal’s dealing it came to light that he had done other misdeeds as CEO of ImClone. These including forging his lawyer’s signature as well as not paying taxes on certain assets and sales.
The Punishment: Waksal didn’t fight the charges that were brought against him and pleaded guilty to securities fraud, bank fraud, obstruction of justice, and perjury. He was sentenced to seven years in prison and ordered to pay more than $4 million in fines and back taxes. These amounts were the maximum allowed by law.
14. Joseph Nacchio
The Crime: For Joseph Nacchio, the tech boom/bust proved to be his undoing. Nacchio came to telecommunications upstart Qwest in 1997. Qwest aggressively expanded through acquisitions and the winning of several major contracts. That helped boost Qwest’s share price enormously.
However, to keep that share price inflated, Nacchio kept reporting very aggressive revenue targets and lied about future contract wins; this helped Qwest continue to find capital and buy out rivals. However, when things began to sour, Nacchio started selling his shares and made about $52 million dollars on the various sales. The government concluded that Qwest had done about $3 billion in fraudulent revenue over Nacchio’s reign and charged him with insider trading and other fraud charges.
The Punishment: Nacchio was convicted on 19 of 42 counts of insider trading. He was sentenced to six years in prison and was required to pay $19 million in fines as well as forfeit the $52 million in gains from the sale.
15. Allen Stanford
The Crime: Allen Stanford’s crimes could be considered the lowest of low: robbing retirees of their hard earned money. After founding wealth management firm Stanford Financial Group—which was essentially a giant Ponzi scheme—Stanford lived a lavish lifestyle. The initial focus of Stanford’s investigation centered on “certificates of deposits” sold to retirees that promised a better than market return, while being 100% safe. That’s an impossible task to achieve, yet retirees sunk more than $7 billion into these vehicles.
Like a regular Ponzi scheme, Stanford would use the proceeds to fund his lavish lifestyle. During the investigation process, regulators found that Stanford’s empire was full of bribery, money laundering and political manipulation in the Caribbean. Stanford also had numerous tax issues as well.
The Punishment: After a major investigation that spanned several countries, Stanford was charged with a multitude of offenses. His trial, which became a media circus, resulted in Stanford receiving a 110-year prison sentence, as well as being forced to pay back $5.9 billion to $6.7 billion in illegal profits plus $861 million in interests. This was on top of a $5.9 billion fine.
The Bottom Line
The answer for the rest of us is simply “crime doesn’t pay.” The vast majority of the people on this list were already making a good living and enjoying the fruits of their success. There simply wasn’t any need to push the envelope. For the average investor, having a long term plan and disciplined research approach are the two ways you can prevent getting caught up in “get rich quick” schemes and other similar frauds. As for breaking Wall Street’s laws? Just don’t do it.