Nov 11, 2026 12:00 PM

ESPN’s Ben Solak crowns Chicago’s general manager a deadline winner after a blockbuster deal for Jeffery Simmons signaled an aggressive, all-in pivot toward a championship window.

Since Chicago Bears General Manager Ryan Poles took over in 2022, he's been involved in a number of trades. 

He started off by trading Khalil Mack to the Los Angeles Chargers for a second-round and sixth-round pick. The following year, he traded Chase Claypool to the Pittsburgh Steelers for a second-round pick. 

In 2024, the Bears were very active when it came to trading. Chicago acquired Chris Williams, Keenan Allen, Darrell Taylor and Ryan Bates. Poles traded down in the 2025 NFL Draft to select Ruben Hyppolite and Zah Frazier. 

This year, Poles topped all of those moves. With a couple of weeks left until the trade deadline, Poles traded with the Tennessee Titans for Pro Bowl and All-Pro defensive tackle Jeffery Simmons. 

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The Bears are going all in on the 2026 season after sending three draft picks to the Titans for Simmons. 

The decision to part with three draft picks was a risky move by Poles, but it's paid off so far. Simmons is everything the Bears hoped he would be. 

In two games with the Bears, Simmons has two sacks, 10 total tackles, three TFLs and two passes defended. 

The trade deadline ended at 3 p.m. CT in Chicago on Tuesday. The Bears didn't make any other moves, but didn't really need to. Plus, the Bears didn't have much draft capital to spend on players after the Simmons deal went through anyway. 

Following the conclusion of the trade deadline, ESPN's Ben Solak went through and named the winners and losers. He had high praise for Poles, calling him one of the winners of the deadline. 

He liked the move for Simmons more than the trade sending Jordan Davis to the Jacksonville Jaguars. 

"It's important to evaluate trades in a vacuum, and two firsts for Simmons was a steep price no matter which way you slice it," Solak said. "But it does bear saying: That trade looks so much less expensive when you see the price the Jaguars paid for Davis, a player who simply (1) does not play as many snaps as Simmons, (2) does not play as many high-value snaps as Simmons does, (3) is not as productive as Simmons on the snaps that they play and (4) has not produced as consistently as Simmons has." 

It's rare to see two defensive tackles get traded at the deadline. The NFL is valuing defensive tackles who can pass-rush more and more. That was clear after the Bears and Jaguars both traded for one. 

The Bears understand how trading for a game-wrecker on defense can impact your team. They've been in this situation before, trading for Mack with the Las Vegas Raiders in 2018. 

It changed the trajectory of the Bears. The team won the NFC North and punched its ticket to the playoffs. 

Things didn't end well for Chicago that season, but teams had to account for Mack between the trenches. The Bears are putting all their chips on Simmons in a similar fashion in the hope that he can propel them to new heights after making a run to the Divisional Round last season. 

They say defense wins championships. Poles know that better than anyone from his time with the Kansas City Chiefs. 

His trade for Simmons made him a winner at the deadline. 

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