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

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)

written by

Luis C. Medina, who you can find on Twitter at lcm1986, has been covering the Chicago Bears at Bleacher Nation since 2017. Since then, he has written about 3 head coaches, 5 play-callers, and 11 starting quarterbacks. Previously, Luis wrote about the Cubs and MLB at BN (2015-16) and worked in the Chicago Tribune sports department (2011-16). He also co-hosted a Cubs postgame show, Outside the Ivy, in 2019.

more bears news

Around the NFL: CMC Injury, Al-Shaair Apologizes, Tomlin Says Pickens Needs to “Grow Up”

The San Francisco 49ers will be without star running back Christian McCaffrey for the foreseeable future—that and more in today's NFL Notes. 49ers Lose Christian McCaffrey to PCL Injury San Francisco 49ers running back Christian McCaffrey sustained a PCL injury...

Weekend Roundup, Eberflus Makes Sad History, Matt Ryan Makes Good Points, and Other Bears Bullets

How did you enjoy your Bears-less Sunday? Things you might've missed while you were putting away the rest of your Thanksgiving leftovers: Matt Eberflus is no longer the Chicago Bears' head coach (this happened on Friday after he told reporters...

Former Bears Coach Matt Eberflus Issues Statement After Firing

Former Chicago Bears Head Coach Matt Eberflus shared a message of gratitude in a statement shared by CBS Sports. This is what Eberflus, who was fired by the Bears on Friday, had to say after his dismissal from the team:...

WATCH: Caleb Williams USC Jersey Number Retirement Tribute Video

Caleb Williams and the Chicago Bears do not play football today. And yet, we still have a sizzle reel worth sharing. In case you missed it, Caleb Williams' No. 13 was retired by the University of Southern California on Saturday...

The Bears Are Reportedly Targeting a Specific Type of Head Coach in 2025

The Chicago Bears have a plan for their next head coach. At least, so says CBS NFL insider Jonathan Jones is reporting. This is what Jones is hearing about the criteria the Bears have set as they go about finding...

Bears-less Sunday, College Football Bedlam, What to Watch in Week 13, and Other Bears Bullets

The Chicago Bears cannot ruin your Sunday by losing a football game. Let that sink in for a moment, then allow yourself to enjoy a day of Bears-less football. Don't forget to set your fantasy lineups. If you insist on...

MUST-READ: Details From Inside the Bears Locker Room After that Ugly Loss to the Lions

The end of Matt Eberflus' time as the Chicago Bears' head coach sounds as yucky as you might have already been imagining. MATT EBERFLUS FIRED: The Decision | The Initial Fallout | The GM Speaks If losing on Thanksgiving in...

Why Did Firing Matt Eberflus Take So Long? Ryan Poles Breaks Silence, Here Comes the Hard Part, and Other Bears Bullets

A heads up: I'll be unavailable for the middle part of the day because I will be spending time with friends knocking something off my Bucket List. Before you ask: No, I'm not seeing Taylor Swift in concert again (although,...

Bears GM Ryan Poles Gets a Vote of Confidence From President Kevin Warren

In case you missed it, the Chicago Bears fired Matt Eberflus earlier on Black Friday. The move represents the first in-season dismissal of a head coach in franchise history. And if you were wondering if General Manager Ryan Poles would...

Eberflus Out, Chaos Reigns Supreme, Keenan’s Revival, Thanksgiving Leftovers, and Other Bears Bullets

I am working through a blister on the index finger of my right hand, so I am trying to be equally proficient and efficient with my keystrokes today. ICYMI: The Chicago Bears have removed Matt Eberflus as their head coach....

Latest News

Buccaneers vs. Panthers Week 13 Tickets – Sunday, December 1, 2024

The Tampa Bay Buccaneers (4-6) face an NFC South foe when they go on the road to play the Carolina Panthers (3-7) on Sunday, December 1, 2024.Where to Buy Buccaneers vs. Panthers TicketsIf you're in the market to buy tickets...

World Juniors Updates: Blackhawks Prospects Moore, Spellacy Invited by US, Lardis Snubbed By Canada

The Blackhawks have a number of prospects hoping to represent their countries in the upcoming 2025 World Junior Championship. On Monday, the United States and Canada announced their preliminary rosters to mixed results for the Blackhawks organization. We expected Oliver...

A Huge 3-Point Turnaround, Nets Are Better Than Expected, Giddey’s Surprising Streak, and Other Bulls Bullets

All things considered, this has to be considered one of the Chicago Bulls' easier weeks of the season. So you know they're about to go 0-4! The Bulls will face the Nets, Pacers, Spurs, and 76ers over the next week....

Let’s Talk About the Cubs’ Recent Offseason Activity and a Weird New Cubs Rumor

[BN_drinks] WEIRD NEW CUBS RUMOR — Generally speaking, I think we're beginning an interesting couple of weeks. Thanksgiving is behind us, the Winter Meetings lie just ahead (Dec. 9-12), the market is moderately active for MLB — at least, relative...

Week 14 NFL Injuries: Latest Injury Reports for Christian McCaffery, Trevor Lawrence & More

A few injury bummers this week, with Swiss Army Knife Taysom Hill looking like he's out for the rest of the year and star running back Christian McCaffrey most likely heading back to the IR after a new injury to...

Around the NFL: CMC Injury, Al-Shaair Apologizes, Tomlin Says Pickens Needs to “Grow Up”

The San Francisco 49ers will be without star running back Christian McCaffrey for the foreseeable future—that and more in today's NFL Notes. 49ers Lose Christian McCaffrey to PCL Injury San Francisco 49ers running back Christian McCaffrey sustained a PCL injury...

Weekend Roundup, Eberflus Makes Sad History, Matt Ryan Makes Good Points, and Other Bears Bullets

How did you enjoy your Bears-less Sunday? Things you might've missed while you were putting away the rest of your Thanksgiving leftovers: Matt Eberflus is no longer the Chicago Bears' head coach (this happened on Friday after he told reporters...

Movement in the Starting Pitcher Market, Optimism and Pessimism on Sasaki, and Other Cubs Bullets

The kids are all back to school today after a mini break for Thanksgiving. House feels extra quiet. That's mostly a good thing from a productivity standpoint, but it's always an adjustment ... The starting pitching market is really cooking...

New York Mets Signing Frankie Montas to a Surprisingly Large Deal

The Chicago Cubs aren't the only team signing a starting pitcher to a surprisingly sizable two-year deal. The Cubs are signing Matthew Boyd to a two-year, $29 million deal, and the New York Mets are signing Frankie Montas to a...

Top Player Prop Bets for Celtics vs. Heat on December 2, 2024

Oddsmakers have listed player props for Jayson Tatum and others when the Boston Celtics host the Miami Heat at TD Garden on Monday at 7:30 PM ET.How to Watch Celtics vs. HeatDate: Monday, December 2, 2024Time: 7:30 PM ETHow to...

Top Player Prop Bets for Bulls vs. Nets on December 2, 2024

You can find player prop bet odds for Nikola Vucevic, Cameron Johnson and others on the Chicago Bulls and Brooklyn Nets heading into their matchup at 8:00 PM ET on Monday at United Center.How to Watch Bulls vs. NetsDate: Monday,...

more bears news