Last week the U. S. Supreme Court agreed to hear an appeal by Skilling of his conviction, asking the court to review the government's use of an "honest services" prosecution in which the defendant is accused of operating for personal gain, and providing the company of his honest services.
In 2002, George Soros was convicted of insider trading and fined more than $2 million by a Paris court. The charges stemmed from 1988 when Soros bought and then sold shares in Societe Generale after receiving a tip about a corporate raid on the bank. Soros denied the charges against him and appealed the ruling, but it was upheld by France's highest court in 2006.
During the 1980's Boesky made millions betting on the aggressive company takeovers that the decade became famous for. "Most of his illegal insider trading was based on mergers and acquisitions trading where he would learn in advance of a perspective takeover," said Coffee. Thought to be a mergers and acquisitions whiz, Boesky was exposed for trading on inside information ahead of company takeovers. In 1987, Boesky was sentenced to 3 ½ years in prison and given a $100 million fine after cutting a plea deal and wearing a wiretap that helped convict other Wall Street titans including financier Michael Milken.
By 1989, Wall Street star Michael Milken was earning hundreds of millions of dollars a year using high-yield junk bonds to fund corporate mergers and acquisitions. Dubbed the Junk Bond King, Milken was indicted by a federal grand jury in March 1989 on 98 counts, including fraud, tax evasion and racketeering.
"All insider trading cases are hard to find the evidence for. It's very easy to hide insider trading and difficult to find a cooperating witness," Columbia's Coffee told ABC News. "You pretty much need a witness to say I tipped him or I heard he was tipped by his own revelation to me."
In the Milken case, that witness was Ivan Boesky who served as an informant for the SEC. After a plea bargain, Milken ultimately only served two years in prison and later became a philanthropist providing funding for academic research.
In 2005, the government built a case against Joe Nacchio, accusing the former telecom chief of lying to Wall Street about Qwest's growth and masking $3 billion dollars in losses. Nacchio, prosecutors said, profited from his knowledge of the company's true financial picture. A 2005 grand jury indictment charged Nacchio sold more than $105 million worth of stock while Quest's true net worth plummeted.
Nacchio was convicted of insider trading in 2007 and began his six-year prison sentence in April. His sentence was later thrown out by a federal appeals panel as excessive and is under review.
Angelo Mozilo lead Countrywide Financial as the company began to lend to increasingly risky homebuyers. By 2008 as home foreclosures skyrocketed to record highs, Mozilo became embroiled in the heart of the mortgage meltdown.