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There are no shortage of “what if” moments that haunt the Chicago Bears franchise. And one of the biggest is what if Chicago never traded tight end Greg Olsen?

The Bears wound up trading Olsen to the Panthers for a third-round pick in 2011, where he spent the next nine seasons in Carolina and became one of the league’s most potent pass-catching tight ends.

Bleacher Report ranked the seven worst trades of the last 20 years, and it wasn’t a surprise to find Chicago trading Olsen to Carolina as one of the worst — at least for the Bears.

(Olsen) put up respectable numbers over a four-year stretch in Chicago but never exactly thrived in Mike Martz’s offense.

As a result, Chicago moved on from Olsen in the summer of 2011 and acquired a third-round pick from the Carolina Panthers.

And the Panthers unlocked an All-Pro.

The primary target for Cam Newton, Olsen turned in five straight 800-yard seasons with three consecutive 1,000-yard years. He twice earned second-team AP All-Pro recognition and played a pivotal role in Carolina winning the NFC in 2015.

Looking back, it was one of the worst trades in Bears history, as Olsen went on to become a three-time Pro Bowler and two-time second team All-Pro with the Panthers.

Olsen had a chance to return to Chicago last offseason when he was released by the Carolina Panthers. Olsen had a nice talk with coach Matt Nagy, which led Olsen to believe that he could finish his career where it all started with the Bears.

I talked to Matt Nagy – he called me with the GM [Ryan Pace] and we talked for like 45 minutes on the phone. They’re asking me questions about routes and ‘what kind of systems you played in, would you be comfortable with code words versus digits, what did you do on your backside routes, what was your leverage reads?’ All that stuff.

So I hang up and I say to my wife, ‘babe, I think they really like me and want to sign me! How cool would it be if life came full circle and we could finish up my career in Chicago? That would be so sick.’

Instead, the Bears went out and signed veteran tight end Jimmy Graham to a two-year deal worth $16 million, which was more than what Olsen signed for with the Seattle Seahawks on his one-year, $7 million deal.

Still, that didn’t hurt as bad as letting Olsen walk in the prime of his career and watching him become one of the best in the NFL on another team.


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