Jerry Richardson only managed to play for the NFL in two years. However, it was during his post-football career where he really made it into the big leagues. He opened up BoJangles restaurant franchises, setting history as the first NFL player to do so. He also managed to own his very own team, leading to his expansion of the Carolina Panthers back in 1993.
When she won the Australian Open, she certainly made quite a career high, along with a Grand Slam title. Yet, it was all cut short due to the nagging knee injuries. Nonetheless, even as she has retired just last year, she will continue to earn from almost all her endorsement deals. Sure, Nike is the exception to this, with a time-based contract, yet she is still making loads of cash.