#12, Steve Hilbert
Years at Company: 1979-2000
Total Value of Severance Package: $72 million
In 1979, Steve Hilbert founded Conseco and built it into a large, successful insurance company, but by 2000, his mismanagement (including a disastrous acquisition of Green Tree Financial) caused the company's stock price to plummet while his personal debt climbed to $181 million. The company ultimately declared bankruptcy in 2002.