| Jon Gruden |
 If looks could kill, Jon Gruden, the former head football coach for the Oakland Raiders and then the Tampa Bay Buccaneers, would have a master's degree in this subject matter. His famous sneer earned him the nickname of Chucky - from the movie series about a killer doll. Of course, that nickname wa
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| Andrew Luck |
 When it comes to negotiating a contract, being young, talented and on the verge of entering the National Football League as the number 1 overall pick in 2012, Andrew Luck's net worth has decidedly just now reached an estimated net worth of $$$.
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| Warren Sapp |
 Warren Sapp was a Miami Hurricane. Then, he became a Tampa Bay Buccaneer. Somewhere along the line he played as an Oakland Raider and now he is trying out to be a United States Bankrupter. Changing teams, affiliations and contracts could not change the inevitable demise of his bank account as the an
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