Chicago Bears Trades That Should Have Been Made at the Deadline But Weren't

Five trades we would have liked to see the Chicago Bears make before the trade deadline passed on Tuesday.

New York Jets cornerback Nahshon Wright (26) kneels in the end zone before a game against the Green Bay Packers at MetLife Stadium, Sep 20, 2026, East Rutherford, NJ, USA. | USA TODAY Network via Reuters Connect

The Chicago Bears made one of the biggest trades of not only 2026, but in NFL history when they acquired Jeffery Simmons after reaching a deal with the Tennessee Titans.

It was one of the biggest trades in NFL history because the Bears became the first team in the common draft era to trade multiple first-round selections for a defensive tackle.

But when the trade deadline rolled around on Tuesday, the Bears did not make another deal despite rumors suggesting they were still in the market for a cornerback, even after the Simmons deal.

We can't say we're disappointed after the blockbuster Simmons trade, but here's the moves we would have liked to see general manager Ryan Poles pull off before the deadline passed.

CB Riq Woolen or Nahshon Wright

New York Jets cornerback Nahshon Wright (26) looks on while warming up before a game against the Miami Dolphins at MetLife Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | IMAGN IMAGES via Reuters Connect

The Bears have a serious concern at the cornerback position, but it's not at the spot we thought it would be.

Entering the year, we assumed the spot opposite Jaylon Johnson would be the concern, as the team was set to start either rookie Malik Muhammad or the perennially-disappointing Tyrique Stevenson.

However, it has been Johnson who has been the biggest issue with his lackluster coverage and tackling, along with Stevenson. Meanwhile, Muhammad has been sensational and the Bears can only hope that will continue the rest of the season.

Jacksonville Jaguars wide receiver Parker Washington (11) catches the ball for a touchdown during the fourth quarter as Philadelphia Eagles cornerback Riq Woolen (2) defends at Tottenham Hotspur Stadium. Mandatory Credit: Nathan Ray Seebeck-Imagn Images | IMAGN IMAGES via Reuters Connect

We would have loved to see either Woolen or Wright added to the Bears' defense.

Woolen was the preferred option because of his past success and ability to thrive in man coverage. Wright, who played for the Bears last season, would've been a solid fallback option to give Chicago's defense the depth it needs.

Both players made sense as trade candidates, too, as they're on teams going nowhere and both have a one-year contract. Wright seemed even more primed to get traded thanks to his not having any role in the Jets' defense.

TE Dallas Goedert or Mo Alie-Cox

Philadelphia Eagles tight end Dallas Goedert (88) during action during the first half against the Jacksonville Jaguars at Tottenham Hotspur Stadium. Mandatory Credit: Kirby Lee-Imagn Images | IMAGN IMAGES via Reuters Connect

Few teams in the NFL utilize 12 and 13 personnel as much as the Bears do. According to Sumer Sports, Chicago deploys those groupings at the fourth-highest rate in the NFL.

So, if you're the Bears, you need to make sure you have reliable, well-rounded tight ends. The Bears did have that before the Cole Kmet injury, but things are a lot shakier now that he's out for the season.

Sam Roush has the makings of a good dual-threat tight end, but he has been about as inconsistent as you'd expect from a rookie and there have been definite growing pains. It's hard to rely on someone like that in a big spot.

Indianapolis Colts tight end Mo Alie-Cox (81) celebrates Sunday, Oct. 18, 2026, after a touchdown catch during the game against the Tennessee Titans at Lucas Oil Stadium in Indianapolis. | USA TODAY Network via Reuters Connect

Then we have Stephen Carlson, who doesn't do much more than block, so defenses don't really have to worry about him being deployed as a pass-catcher when he's on the field.

Goedert would have been the dream addition here because he's a huge threat in the passing game as well as a good blocker. Alie-Cox would have made for a fine consolation prize with his solid blocking and serviceable pass-catching ability.

We thought both players had a good chance to get moved with the situations their teams are in, and with both players north of 30 and in the final year of their deals. We were wrong.

EDGE Khalil Mack

Los Angeles Chargers linebacker Khalil Mack (52) is introduced prior to the game against the Las Vegas Raiders at SoFi Stadium. Mandatory Credit: Gary A. Vasquez-Imagn Images | IMAGN IMAGES via Reuters Connect

A few weeks before the deadline, FOX Sports' Jay Glazer reported that the Bears had put in a call for Mack, so there was at least some interest in him on the Bears' part.

Edge rusher probably wasn't the biggest need the Bears had, but there is no doubt Mack was the one trade Bears fans wanted most and it all seemed perfectly set up for a Mack-Bears reunion.

The Bears had a need for more depth at edge rusher and the Chargers are in the midst of a nightmare season that has them sitting at 0-8 and going nowhere.

Teams in Los Angeles' situation would normally be heavy sellers, and a veteran like Mack who could retire at any moment would normally want out of that situation.

But, neither of those things turned out not to be the case, as the Chargers were unwilling to trade Mack and, more importantly, Mack wanted to stay with the Chargers.

The real roadblock for the Bears, assuming they were still wanting to make a deal, was Mack because if he had requested a trade, the Chargers would have done it. Instead, he'll be riding it out with the Chargers, who will need the miracle of all miracles to make the playoffs.

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