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This time is different for the Chicago Bears

The Chicago Bears’ blockbuster trade for Jeffery Simmons drew a lot of comparisons to their 2018 blockbuster trade for Khalil Mack. Both defenders were acquired to give a team with Super Bowl aspirations a boost, but the big difference is…

By Lester A. Wiltfong Jr · Windy City Gridiron

Published: Tuesday, 3 November 2026 at 11:30 PM

Key Things to Know

Windy City Gridiron argues the Bears are better positioned for sustained success than during their 2018 season.
The Chicago Bears acquired defensive tackle Jeffery Simmons in a blockbuster trade.
The writer believes the pairing of Ben Johnson and Caleb Williams provides proven leadership for the franchise.

The Story in 60 Seconds

Windy City Gridiron argues that the Chicago Bears' blockbuster trade for Jeffery Simmons is more sustainable than their 2018 move for Khalil Mack. The outlet highlights that Chicago now possesses a proven head coach and quarterback partnership with Ben Johnson and Caleb Williams following a victory over the Seattle Seahawks.

The writer contends that unlike the unproven pairing of Matt Nagy and Mitchell Trubisky in 2018, the current Bears have demonstrated clear improvement. Adding Simmons to Dennis Allen's defense is described as a calculated gamble for a team already positioned for a postseason run.

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This time is different for the Chicago Bears

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