Derek Jeter

Retired: 2014

Career Earnings: $269 million

Est. Net Worth: $185 million

Another heavily-marketed athlete who has been able to be successful post-retirement is former MLB player and Baseball Hall of Famer, Derek Jeter. His talent made him a celebrity and he has spent retirement pursuing his various business interests. He partnered with Simon & Schuster for a time, later forming his own publishing company, Jeter Publishing.

Jeter Publishing sells books for adults, children, and schools. Jeter also runs the website called The Players Tribune. Jeter announced in 2015 that he would be opening a restaurant in the Tampa International Airport, to be named after The Players Tribune.