Ten Years After the Jay Cutler Trade, GM Jerry Angelo Offers a Hint of Regret

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Ten Years After the Jay Cutler Trade, GM Jerry Angelo Offers a Hint of Regret

Chicago Bears

It was on this date in 2009, when the Chicago Bears traded two future first-round picks and quarterback Kyle Orton to the Broncos as part of a larger deal that sent quarterback Jay Cutler to Chicago. The Cutler era was a disappointment for any number of reasons. And frankly, we don’t need to dive into those and pick them apart on April 2, 2019.

Instead, we do need to take some time to go through the oral history of the deal, as shared by Kevin Fishbain and Dan Pompei of The Athletic.

With perspectives from GM Jerry Angelo, Director of Pro Personnel Bobby DePaul, President Ted Phillips, ESPN radio personalities Carmen DeFalco and Marc Silverman, and many others, there is so much to dive into with this piece. But I would like to highlight one comment Angelo made that piqued my interest.

“We liked Orton,” Angelo said. “In hindsight, maybe keeping him would have been the best thing.”

HINDSIGHT! Oh, hindsight can be so cruel. Let’s talk through it.

Keeping Orton and using those picks to supplement the team around him would have been a worthy alternative than investing in Cutler as some sort of quarterback savior. But as Angelo points out, the opportunity to acquire a rare talent like Cutler doesn’t often present itself in the NFL. So when the deal is available, any general manager worth a darn is going to try and get a deal done. The Bears out-maneuvered Washington to make it happen, but it came at the cost of losing a respected player of the locker room.

One common thread throughout the piece is the respect for Orton. At the time the trade was made, Orton was a seasoned starter who earned the respect of his teammates through his play and his conquering of tough times. Orton was thrust into a starting role as a rookie in 2005 when Rex Grossman was injured, then won the starting job some years later and relegated Grossman to backup duties. Without re-living the Orton years, I think it’s safe to say that he was a perfectly cromulent quarterback. That is to say, he was a good, serviceable starter. But didn’t have Cutler’s upside. And that’s why the trade happened. Full stop.

The Jay Cutler Trade should have been a turning point for the Bears franchise.

After years of middling with status quo at the quarterback position and not investing in a talented player with upside at the game’s most important position, GM Jerry Angelo pulled the trigger on a deal that landed the Bears a premier talent in the prime of his career. It was supposed to be the dawn of a new era for Chicago football, one that pushed aside an offensive scheme that made “three yards and a cloud of dust” look innovative for a system that embraced the forward pass. Of course, we now know that didn’t quite happen.

I’m not sure what the future holds, I feel good about the present. At minimum, I feel better now than I did when the Bears traded for Cutler in 2009. That’s saying a lot, because I was pretty jacked about the deal. Perspective can be a valuable tool in growth. Much has been learned since the Cutler trade. And while living through that era of Bears football was rough sledding, without it, I’m not sure where the Bears would be as an organization or where we would be as fans. All I know is I’m ready to move on with this era of Bears football. Bear. The. Heck. Down.

(Photo by Jonathan Daniel/Getty Images)

Author: Luis Medina

Luis Medina is a Writer at Bleacher Nation, and you can find him on Twitter at@lcm1986.