5. Drew Brees-$131,455,000
The diminutive New Orleans Saints quarterback has earned two offensive player of the year awards and has thrown for over 5,000 yards four times. Brees came to New Orleans on a relatively low quarterback contract, as the former Purdue Boilermaker had not yet proved himself. With one Super Bowl victory and two massive contracts under his belt, Brees approaches the $150 million milestone by cashing on his fame in a city that suffered for decades as a perennial loser. Brees has also earned substantial income investing in dilapidated New Orleans properties that took the brunt of Hurricane Katrina.