Bears Trade for Jay Cutler
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The Bears thought they had a steal after Josh McDaniels had essentially run Cutler out of town in Denver. After all, Cutler had just thrown for over 4,500 yards in 2008 and looked like he would only get better. Thus, the Bears traded Kyle Orton, two first-round picks, and a third-round pick to get Cutler. But the Bears ended up being terribly wrong. Cutler ended up spending eight years in Chicago, with the Bears reaching the playoffs just once in that span. The longer Cutler remained with the Bears, the worse things got and the worse that trade looks.
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