Stephan Savoia / Los Angeles Times
The violation that sent Martha Stewart to jail is relatively small-scale compared with other schemers on this list, but her saga captured the public's attention. In 2001, the domestic mogul sold nearly 4,000 shares of ImClone Systems stock -- about $228,000 worth. She had received an insider tip from her broker that the federal Food and Drug Administration was planning to deny approval to the company's cancer drug. Soon after, the agency made its announcement and shares took a double-digit plunge. Later, as accusations of a coverup grew, Stewart resigned her short-lived position as board member at the New York Stock Exchange and stepped down as chief executive and chairwoman of her Martha Stewart Living Omnimedia company. She was convicted in 2004 of lying to investigators, conspiracy and obstruction of justice and sentenced to five months in prison in West Virginia. After her 2005 release, she spent two years in supervision, partly served in home confinement with electronic monitoring. The media entrepreneur has since regained much of her involvement in MSLO.