1. Jay Cutler
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The Chicago Bears might’ve won out on the five-team bidding war for the services of Jay Cutler in 2009, but they never ever got the return on investment with Cutler, given the two first-round picks and a third round picks they traded to the Denver Broncos; that’s not even mentioning the $102 million that the Bears have paid Cutler since acquiring him. In exchange for all of that, Cutler has never thrown for 4,000 yards in a season, and has never thrown for more than 28 touchdowns. Oh, and he’s also won exactly one playoff game in Chicago.
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