WEDNESDAY JULY 30
Remember, Someone Else Is Always Worse Off Than You

Even better if that someone else happens to be a famous billionaire dealmaker, like, oh, say, T. Boone Pickens. Here's how the world-renowned oilman got a profound drubbing by betting alongside one of his cronies (which, by the way, we recommend you only do if you're sure you're going to make a killing, which, we can attest, he did not).

July 2008

Oil billionaire T. Boone Pickens took a bath by betting with Carl Icahn in the battle to take over Yahoo. Pickens says he sold his 10 million shares of Yahoo. Pickens, who says he was simply following Icahn and admits he doesn't know how to send an email, bought his shares in early may, likely paying between $25 and $27. Yahoo is now trading five dollars lower, in the $20 to $22 range. That puts Pickens' loss at around $50 million.

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