LeBron James — Before LBJ signed with the Cleveland Cavaliers right out of high school in nearby Akron, Ohio, James signed a Nike deal worth $90 million over seven years. His first shoe, Air Zoom Generation, sold 72,000 pairs in the first month at a cost of $110. He also owns a marketing company, LRMR, which has secured endorsement deals with the likes of Nike, Sprint and Upper Deck.