The 20 Wealthiest NFL Players of All Time

NFL Commissioner Roger Goodell and NFLPA Executive Director DeMaurice Smith celebrate the signing of the league's new collective bargaining agreement.

NFL Commissioner Roger Goodell and NFLPA Executive Director DeMaurice Smith celebrate the signing of the league’s new collective bargaining agreement. | Michael Loccisano/Getty Images

Across the board, NFL players get the short end of the stick when it comes to being paid for their unreal athletic ability and performances. Their contracts are largely unguaranteed, their career windows are short — probably because playing in a football game, even at levels below the National Football League, is comparable to a car accident — and their endorsement opportunities are generally slim.

In fact, aside from the handful of guys who get corralled by reporters after the game and those that are just flat-out massive human beings, there’s a good chance that when most NFL players take off their pads, helmet, and jersey and slip out into the night, they will go unnoticed.

But some of them are able to bankroll their fame and (relative) fortune into more fortune, and sometimes even more fame. From licensing deals to owning franchises to eventually owning an NFL team, à la the late Al Davis, the money’s out there if the player is savvy enough to seek it. Here are 20 of the savviest NFL players, both past and present — the guys who have been able to take their athletic acumen and turn it into continued financial success.

20. Drew Bledsoe

Net worth: $48 million

Although quarterback Drew Bledsoe was once a No. 1 overall pick (1993 NFL Draft), he’s probably most known for being the guy whose injury paved the way for Tom Brady to take over the reins for the New England Patriots. To our surprise, however, Bledsoe also managed to earn himself another title; that of one of the wealthiest football players in history.

Thanks to a 14-year NFL career that included four trips to the Pro Bowl, Bledsoe compiled a net worth of $48 million. Imagine what this figure might have been had he not lost his starting gig in New England.