No. 5: CIT Group
Company value at time of bankruptcy: $80 billion
Commercial lender CIT Group (NYSE:CIT) was one of the first victims of the financial crisis. The commercial lender was up to its eyeballs in bad debts and foul mortgages, and became a bank holding company to qualify for a TARP bailout. The bailout didn’t help stave off the worst, however, and the company went under in November 2009 with a total price tag of $80 billion. Most miraculously, CIT maintains an unbroken history as a publicly traded stock — though it went near zero in 2009, but bounced back fast enough to avoid delisting. Of course, all previous shares — both common and preferred — were canceled, so don’t think that means folks hanging onto their shares got anything for their trouble.