His push into the mortgage market went supremely sour this year and cost him his job. He was ousted on Nov. 29 after it took a $2.55 billion cash infusion from Citadel Investment to save the company. But based on the ailing $3.65 share price, investors aren't too optimistic about E*Trade's future.

E*Trade started the year at $23 a share, so as a big shareholder, Caplan is out millions on the fallen share price. He did get out the door with a big package, which hardly seems fair but is the way executive compensation packages are set up these days. Clearly his earning potential going forward is not so hot.

Now Caplan is busy unloading his shares at this bargain basement price. Reuters reports that on Dec. 14 he sold 300,000 shares -- his first sale that wasn't tied to exercising options. Caplan is still a director at the company. Ironically, Caplan took over when the stock was down to $3 a share after the dot-com infused leadership of Christos Cotsakos went south. For a while Caplan was the hero, but it's pretty easy to forget that now with the stock back in the low single digits.

Be sure to check out other Money Losers of 2007.