#1. The Jay Cutler Contract Extension – 2014
This might be the most frustrating decision, from a fan’s perspective, in the history of the franchise. Cutler signed a seven-year $126.7 million contract extension back in 2014 worth $54 million guaranteed. They did this just after Cutler and the Bears finished 8-8 in their first season under Trestman.
Since that decision, the Bears have finished in fourth place in their division three years in a row. Each of those seasons Cutler was ranked as one of the highest paid quarterbacks in the league and the Bears had 12 total wins with him at quarterback, they also had 33 losses. The team wasn’t the only thing that was bad though. The first year after signing the extension Cutler tossed 18 interceptions, his highest season total going back five years.
Had it not been for the one good season Cutler had under Adam Gase in 2015, this could arguably be the worst decision the franchise has ever made. The main reason it was SO bad was because they could’ve just franchised him. The Bears had the ability to use their franchise tag and let Cutler earn his money, like most players do. Instead, they gambled on improving Cutler’s happiness, which is next to impossible given his public persona, and gave him $54 million and seven years. Here we now sit, three short years later, and he’s likely going to be cut which is going to void off the four final years of the contract…. more than half of it.
Thanks to Phil Emery and the McCaskey family.
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