NFL power rankings: 30 richest active players

14. Jay Cutler – $112,196,087

Jay Cutler has been one of the more frustrating players in recent memory, possessing ungodly skills and a terrible attitude to go with it. Time and time again, teams have thrown a ton of money at him, hoping he would finally reach his full potential. At 33 years old, his best football may be behind him, and it looks like his days as the franchise quarterback in Chicago are certainly over.

Cutler’s career started in Denver, where the Broncos selected him with the 11th overall selection in the 2006 NFL Draft. A product of Vanderbilt University, Cutler was given a 6yr/$48 million dollar rookie contract, as the team expected him to be their next John Elway. That did not work out, and in 2009, he was traded to the Chicago Bears for Kyle Orton. The Bears wasted no time signing him to a long-term deal, giving Cutler a five-year, $50.37 million deal with $20 million in guaranteed money.

In 2014, the Bears doubled down on their investment in Cutler, giving him a contract extension of over $126 million dollars. The seven-year deal included $54 million in guaranteed money, though he will likely not be in Chicago to earn the full $126 million. Cutler has made only one Pro Bowl during his career, back in 2008 with the Broncos, and you have to scratch your head as to why he never fully reached his potential despite the fact that he was given so many chances.