1. Howie Hubler (Loss: $9 billion)
Howie Hubler was a bond trader from Morgan Stanley, who lost $9 billion after gambled on mortgages that appear to be good on paper, but turned out to be completely worthless. He left Morgan Stanley and even given a few dozens millions of dollars in pay. Hubler quietly returned to the mortgage business by establishing a firm in Rumson, New Jersey with other former Morgan Stanley colleagues. Interestingly, he is now working as a consultant for homes that worth less than the amount of mortgage.