Peyton Manning

Peyton Manning earned approximately $249 million in NFL salary over 18 seasons with the Indianapolis Colts and Denver Broncos, making him one of the highest-paid players in football history at the time of his retirement. But Manning's off-field income has dwarfed his playing earnings. His endorsement portfolio during his career was the largest in the NFL -- Nationwide, Papa John's, DirecTV, Gatorade, Nike, and MasterCard all paid premium rates for his folksy, everyman appeal.

Manning owned 31 Papa John's franchise locations in the Denver area, which he sold for a significant profit after his playing career ended. He also invested in multiple businesses and became a co-owner of the NFL's expansion discussions. His media career has flourished post-retirement: the ManningCast on ESPN, featuring Peyton and brother Eli, has become one of the most popular alternative broadcasts in sports television, generating substantial appearance fees and production revenue.

What separates Manning from other wealthy quarterbacks is the sheer volume of his commercial activity. He appeared in more national TV advertisements than any athlete of his generation, and his willingness to be self-deprecating and comedic made him the most bankable pitchman in football. His net worth of $250 million reflects a career where the endorsement check was always bigger than the game check.