Year(s) of endorsement: 1996-Present
Estimated money made: $50 million
Allen Iverson's fall from grace has not been fun to watch, but Reebok at least was looking out for the best interests of "The Answer" when they signed him to a lifetime endorsement contract in 1996. Of the $50 million Iverson was given, $30 million of that reportedly went into a trust fund that A.I. will not be allowed to use until 2030. Unfortunately, there is no way he will get all $30 million; his debts and a costly divorce settlement mean that on the day he can finally get the money, Iverson will have to give it all back to his creditors and his ex-wife.