AP Photo/Chris Gardner
10 R Foster Winans
AP Photo/Chris Gardner

R Foster Winans was sentenced to 12 months in 1987 and served nine. As a columnist for the Wall Street Journal, Winans gave advanced copies of his influential column to stockbrokers, who used the information to make money in the stock market. Winans’ cut of the deal was $31,000. His case made it to the Supreme Court, which split 4-4 on whether it was considered insider trading.

9 Brian Callahan and William Jackson

Brian Callahan and William Jackson were fined $37,500 in 1990. Jackson worked at a printing plant that printed Business Week magazine and would supply Callahan with advanced copies prior to the opening of the stock market. The pair only made about $20,000 each for their efforts.

8 Christopher Balkenhol

Christopher Balkenhol was levied fines totaling $198,000 in 2007. Balkenhol gleaned information about Oracle from his wife, who had a position at Oracle that gave her access to sensitive information. She was unaware of his illegal investments. Balkenhol used the information to buy stock in a company that Oracle was trying to buy. He ended up making $82,000 in illegal profits. He settled without admitting guilt or innocence.

7 Hafiz Naseem

Hafiz Naseem was charged in 2007 with giving tips to investors who used them illegally. He used his position at Credit Suisse to warn a Pakistani investment banker, who made $7.5 million in schemes about pending mergers. Naseem got his information from a printer used by employees who had knowledge of potential deals.

6 Matthew Devlin
Brian Zak, Sipa Press

Mathew Devlin, a former Lehman Brothers broker, garnered insider tips from his wife. Delvin’s wife worked at a high-powered public relations firm in 2008. He would secretly learn valuable investment information by being close to her and monitoring her travel schedule. Devlin’s information earned millions for his friends that he tipped off. In return, he was given gifts, including cash. His wife was not charged.

5 Samuel Waksal
AP Photo/Mary Altaffer

Samuel Waksal was fined $4 million in 2002 and sentenced to 87 months in prison. He was charged with insider trading but pleaded guilty to other charges, such as income tax evasion and obstruction of justice. Waksal sold thousands of shares of stock in Imclone, knowing it would drop once news about a promising drug was announced. This case became more famous because it involved Martha Stewart, who also sold shares prior to the drop. Stewart served time for obstruction of justice.

4 Martin Siegel

Martin Siegel was fined $9 million in 1987 and sentenced to two months in prison. While working at Kidder, Peabody & Co., Siegel would provide confidential information to Ivan Boesky in exchange for large sums of cash. The surprisingly light prison sentence, handed down by U.S. District Judge Robert Ward, was explained as compensation for his “cooperation, contrition and candor.”

3 Joseph Nacchio
AP Photo/Ed Andrieski

Joseph Nacchio was fined $19 million in 2007, sentenced to six years in prison and ordered to forfeit $52 million in gains. Nacchio, a Qwest executive, sold shares of Qwest after learning from insiders that the company would miss its financial targets.

2 Jeffrey Skilling
AP Photo/Pat Sullivan

Jeffrey Skilling was fined $45 million in 2006 and sentenced to 24 years in prison. Skilling sold millions of dollars worth of shares in Enron before its collapse. Charged with 10 counts of insider trading, he was only convicted on one. He was also convicted of other crimes, including fraud and conspiracy, which contributed to his lengthy prison term.

1 Ivan Boesky
AP Photo/G. Paul Burnett

Ivan Boesky was fined $100 million in 1986 and sentenced to 42 months in prison, although he only served 22 months. He was charged with making $50 million in illegal profits by investing on tips he received from others. He pleaded guilty to related charges in a plea bargain.