10 Real-Life Gordon Gekkos

NEW YORK ( TheStreet) -- It takes a special kind of narcissist to want to be Gordon Gekko, but a stable of criminal misanthropes to inspire the Wall Street character's existence.

Friday's release of that film's 23-years-overdue sequel, Wall Street: Money Never Sleeps, reacquaints America with Gekko, one of its most famous modern caricatures -- the archetypal cutthroat corporate raider and embodiment of 1980s excess. Director Oliver Stone assembled Gekko from elements of his own personality and those of of Creative Artists Agency founder and former Disney ( DIS) exec Michael Ovitz, former corporate raider and current art patron Asher Edelman and investor/financier Carl Icahn. Yet none of those people spent a day in prison, never mind the more than two decades Gekko spends in the clink for insider trading between the first film and the sequel.

Stone needed a criminal mind for his Frankenstein monster, and the '80s were replete with them. Between Michael Milken, Ivan Boesky and Dennis Levine, just to name a few, Stone found just the right mix of miscreant muses to ensure Gekko's rise would end in a prison term. Michael Douglas' Gekko may have emulated those characters a bit too well, as Wall Street screenwriter Stanley Wieser told the Los Angeles Times two years ago that he's still approached by people who tell him the movie changed their lives and made them want to get into investment -- just to be like Gekko. During a "making of" segment on the Wall Street 20th anniversary DVD, Douglas and his Wall Street co-star Charlie Sheen said similarly misguided individual have relayed the same sentiments to them since the first film's release.

For those still unfamiliar with Gekko's story, TheStreet has put together a list of notorious Wall Street ne'er-do-wells that either inspired or drew inspiration from Douglas' slick-coiffed corporate criminal:

Dennis Levine

Crime: Insider trading. Incarcerated: April 1987 to September 1988.

Once the managing director of Drexel Burnham Lambert -- a firm that had more than its share of problems during the Wall Street era -- Levine spent much of his career engaged in insider trading that earned him millions. When the Securities and Exchange Commission decided to investigate Levine based on information from his previous employer, Merrill Lynch ( MER), they discovered other discrepancies that led to Michael Milken, Ivan Boesky and, basically, the end of the go-go '80s. Levine, meanwhile, was sentenced to two years in prison, paid $362,000 in fines and forfeited his profits from insider trading. He later became president of the Adasar Group financial consulting firm and gave ethics lectures at various universities.

Michael Milken

Crime: Securities and tax violations. Incarcerated: March 1991 to January 1993.

Once known as the "Junk Bond King," Milken basically creating the market for high-yield bonds, Milken was indicted on 98 counts of racketeering and securities fraud after an insider trading investigation of his firm, Drexel Burnham Lambert. Before Milken, it was a rare to use the RICO Act against someone with no ties to organized crime. Milken eventually pleaded guilty to six lesser charges in exchange for a reduced sentence, but had to pay $1.1 billion in fines and restitution to investors and was banned from the securities industry for life by the Securities and Exchange Commission. Still worth more than $2 billion, however, Milken is now a financier and philanthropist who has funded the Melanoma Research Alliance, the FasterCures health think tank and the Prostate Cancer Foundation after battling prostate cancer.

Ivan Boesky

Crime: Insider trading. Incarcerated: December 1987 to April 1990.

This is the man who inspired Gekko's "Greed is good" speech by telling students at Berekley in 1986 that "You can be greedy and still feel good about yourself." Boesky made more than $200 million betting on company takeovers after receiving tips from within the affected companies. Sure, it was illegal even then, but nobody was checking into it before Levine's investigation put Boesky in the SEC's crosshairs. Boesky went from the cover of Time magazine a year before his sentencing to ratting out Milken to the SEC for a reduced sentence less than a year later. The SEC fined him $100 million and banned him from working in securities for life, but he lost millions more making restitution to investors and even had his name taken off the library at the Jewish Theological Seminary in New York. To this day, his name is synonymous with corporate fraud.

Dennis Kozlowski

Crime: Misappropriation of corporate funds. Incarcerated: September 2005 to present.

Gordon Gekko had nothing on former Tyco CEO Kozlowski when it came to excess. He got $81 million in unauthorized bonuses. He charged $14.7 million in artwork to the company. He charged the company for his $30 million New York apartment with $6,000 curtains and a $2 million party for his wife on an Italian island that included human statues and an ice sculpture of Michaelangelo's David urinating vodka -- billed as a business meeting. Joining Boesky in the ranks of felonious donors, his alma mater Seton Hall University didn't even wait until he was sentenced to take his name off an academic building he'd donated in 1997. He's serving a sentence of 8.33 to 25 years.

Jeffrey Skilling

Crime: Conspiracy, insider trading, securities fraud, etc. Incarcerated: December 2006 to present.

The former Enron president's future is still up in the air, but he was convicted after selling $60 million of Enron stock just before its bankruptcy and dissolution. The bankruptcy cost 20,000 workers their jobs and cost investors billions. Though originally sentenced to 24 years and four months in prison, the Supreme Court nullified his sentence in June, saying his crimes didn't constitute the "honest services fraud" of which he was convicted. He still awaits resentencing from the 5th U.S. Circuit Court of Appeals, but it doesn't return the $45 million he was fined and likely won't lead to all of his convictions being overturned.

Bernie Madoff

Crime: Eleven offenses including securities fraud, wire fraud, mail fraud, money laundering and perjury. Incarcerated: July 2009 to present.

Four months into his prison sentence, Bernie Madoff got into a fight with another inmate at the Federal Corrections Institution Butner Medium in Butner, N.C. Considering that the people who he defrauded out of billions in one of the largest Ponzi schemes in history wanted to inflict much greater pain on him, he got off lightly. Among those he defrauded during his years as a broker and investment adviser: The Innocence Project, Yeshiva University and The Ellie Wiesel Foundation. Clients René-Thierry Magon de la Villehuchet and William Foxton killed themselves after being wiped out. Madoff was sentenced to 150 years in prison, and his assets are still being liquidated and disbursed to former clients. His tax penalties alone total $1 billion. Compared with Madoff, Gekko looks like a pickpocket.

Allen Stanford

Crime: Accused of fraud, conspiracy and obstruction. Incarcerated: June 2009, awaiting trial in January.

Once a popular and respected financial pundit, Stanford has been accused of defrauding Stanford Finanical Group clients of more than $8 billion in what the SEC has dubbed a "massive Ponzi scheme." After consistently bringing in higher-than-market returns to its clients, Stanford and his associates are accused of falsifying group records to hide their fraud. His Bank of Antigua and Stanford Bank Venezuela have been taken over by local concerns. Antigua has stripped him of his knighthood and is looking to seize his island property and revoke his citizenship. At least Gekko kept his business stateside.

Rafaello Folleri

Crime: Fraud and money laundering. Incarcerated: October 2008 to present.

To tabloid readers, Italian playboy Folleri's real crime was breaking actress Anne Hathaway's heart. To investor Ron Burkle, who lost $50 million when Folleri misappropriated funds meant to buy property from the Roman Catholic church, and to parishes who saw their administrators bribed by Folleri for access to distressed property, the former CEO of the Folleri Group real estate firm's crimes were much greater. As it turned out, Folleri was posing as the Vatican's lead real estate agent, which led to his scandal's Vati-Con moniker. Though Hathaway had her journals seized by the FBI in connection to the case, it's Folleri who had to answer to a higher authority.

Martha Stewart

Crime: Conspiracy and obstruction. Incarcerated: October 2004 to March 2005.

How does one turn a domestic doyenne into a corporate criminal? Start by having the Martha Stewart Living Omnimedia ( MSO) founder's broker tell her to sell nearly 4,000 shares of her ImClone stock in December 2003 when one of ImClone's antibodies failed to get FDA approval. Add a 16% drop in share price a day later, $230,000 in savings and a few lies and you get a trip to the pen and some home confinement. ImClone founder Sam Waksal took the brunt of the fallout, sentenced to seven years in prison and a fine of $4 million, but he's not nearly as famous. Any good Gekko needs a little hubris, and Stewart's appearance on the Early Show, where she answered ImClone questions by stating her preference for focusing on her salad, showed a surplus of it. That's not a good thing.

Henry Blodget

Crime: Accused of civil securities fraud. Incarcerated: Never convicted, but settled with the SEC for a $2 million fine and $2 million payback of ill-gotten profits.

When Elliot Spitzer was forced out of the governors' mansion, few had reason to applaud harder than Blodget. While Blodget was head of the global research team at Merril Lynch, he e-mailed stock assessments that differed vastly from the information Merril Lynch was providing investors. In 2002, Spitzer, then New York's state attorney general, published those e-mails, resulting in SEC charges. Blodget out-Gekkos Gekko by avoiding a prison term, but absolutely trumps him by seeing his accuser humiliated from the comfort of his own home.

-- Written by Jason Notte in Boston.

>To contact the writer of this article, click here: Jason Notte.

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Jason Notte is a reporter for TheStreet.com. His writing has appeared in The New York Times, The Huffington Post, Esquire.com, Time Out New York, the Boston Herald, The Boston Phoenix, Metro newspaper and the Colorado Springs Independent.

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