This is going to bug me eight degrees of crazy if I can't remember who this character is...

I think he was a rich African-American character who was in college running a small time gambling ring out of his dorm until his father found out about it and expelled him out of his life and out of money. Now his white gambling buddy is blackmailing him into laundering money.

I can't remember if this was Lost, or Smalleville, or something else.