8. Dan Snyder
TEAM (YEAR PURCHASED): Washington Redskins (1999)
W-L (WINNING PCT): 80-96 (.455)
COMPLEX SAYS: We should all ask Dan Synder for some money. The man gives it away like it's going out of style. He wasted millions on injury prone Lavar Arrington, an over-the-hill Deion Sanders, and a down-and-out Bruce Smith. Then, Danny Boy decided to give massive amounts of skrilla to Albert Haynesworth and DeAngelo Hall. And let us not forget about the Shannahan/Haynesworth/McNabb controversies. It's a mad house in DC, Redskin fans need to attempt a coup.