Jay Cutler
What exactly did Cutler do during his tenure in Chicago to make the Bears think he should have gotten a seven-year, $126 million deal? To be fair, the contract didn’t come with a lot of guaranteed money on the backside, allowing Chicago to quickly correct the mistake. But at the time, Cutler had led the Bears to just two 10-win seasons in six years, so it was still a head-scratcher.
Predictably, things fell apart quickly, as the Bears went 6-9 in 2015 and just 1-4 in Cutler’s starts in 2016 before a shoulder injury ended his season. The Bears quickly got out of this contract by releasing Cutler, who then retired. He came out of retirement to spend one more year with the Dolphins. But the bottom line is that Cutler was out of the league three years after getting that seven-year deal.