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.

Jack Nicklaus

Jack Nicklaus is considered to be a legendary golf player, hence earning him the nickname “Golden Bear”. He has helped design many golf courses all over the world, around 390 of them. He also has a partnership with Perry Ellis for clothing and apparel named after him. This product line generates 250 million dollars every year, making him a multi-millionaire even after having slowed down tremendously from his peak years in professional golf.

David Beckham

David Beckham spanned a 20 year career in international football, making him a definite legend. He even married a freaking Spice Girl, for crying out loud. He also happened to have earned pretty big right after an entire year post-retirement, partnering with Global Brands Group and Diageo. This led him to net over 20 million dollars upfront.