Joe Nacchio, Qwest
Insider trading was what tripped up Qwest CEO Joe Nacchio who was found guilty of using information he gleaned from his position in order to sell $52 million in stocks at an advantageous price. He told Wall Street that the telecom provider would meet its revenue goals, based in part on his belief the company was in line to land some hefty federal contracts. In 2007, he started serving a 70-month federal jail term in Pennsylvania. He fought for and won a retrial, was reconvicted and once he was in jail, sued his lawyer for allegedly over charging him for his defense. He says the bill was more than $25 million.