No. 7: Conseco
Company value at time of bankruptcy: $61 billion
Insurer and financial firm Conseco was a little too aggressive with buyouts and acquisitions. Across the 1990s, it sucked up Colonial Penn and — most damningly — Green Tree Financial, a financier of mobile-home sales. It filed for bankruptcy in 2002 after the recession of the early aughts, with a total price tag of about $61 billion at the time it failed. The company re-emerged in 2003 and remains in operation as a privately held company. The holding company that is Conseco’s parent was renamed CNO Financial Group in 2010.