Investors who took Cramer's advice would have taken a 30 percent hit to their portfolios as the stocks of financial titans such as Citigroup and Merrill Lynch got hammered by the mortgage crisis.
On the other hand, investors savvy enough to follow Bolling's bet on gold and oil would have hit the jackpot, as the hot commodities jumped over 60 percent in the same period.
Cramer, through a spokesman, blamed his loss on Federal Reserve Chairman Ben Bernanke's failure to cut interest rates more aggressively.
"The bet turned on Jim Cramer emphatically calling for the Fed to ease rates. The Fed didn't follow Jim's advice, and as a result he'll be happy to write a check to the charity of Eric's choice," a spokesman said.
Cramer can't even lose gracefully.
He is a true loser, through and through.