Michael Strahan

Formerly a player for the NY Giants, Strahan has made a pretty successful crossover to the world of media. Co-hosting “Live with Kelly and Michael” with Kelly Ripa, he definitely has transformed into a media darling. He is also a sports analyst for Fox Sports. This highly famous pitchman has even garnered partnership deals with Dr. Pepper, Vaseline and Subway, among many others.

Arnold Palmer

Arnold Palmer hasn’t played a game in more than 4 decades. However, he continues to be a relevant name in golf. In Asia alone, he has 500 Arnold Palmer stores, with 200 more opening in the course of the next eighteen months. He also manages to make 25 percent of revenues from AriZona Beverage Co. with his self-named beverage line. How’s that for a lasting legacy?

Pele is a legend in the world of international soccer, mainly for being among the best players ever as well as the inventor of the Pele Kick. However, he has recently become quite the target for many sponsoring brands, such as Vivo, Hublot, Volkswagen and Procter & Gamble. He has also earned himself a sponsorship deal with G-Form for creating revolutionary shin guards for players. With the Olympics to be set in Brazil this coming 2016, you can be sure Pele is going to capitalize on this and make even bigger money.

Jerry Richardson

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.

Magic Johnson

Magic Johnson was definitely the epitome of a perfect point guard back in the 80s and early 90s. This led him to being a highly paid NBA player. Years after retiring from the game, he has increased his reach in the world of basketball by investing in the creation of a 2nd MLS franchise in Los Angeles. The cost will reportedly be around 250 million dollars, which is going to be contributed to by other stockholders. Nonetheless, along with a new stadium in the process of construction, you can bet your bank that he’ll get even fuller pockets in the years to come.