Colin Cowherd compares Bears to 1985 team after blockbuster Jeffery Simmons trade

Comparing any Bears' team to the '85 squad might seem sacreligous, and, yeah, we're a far cry from really being able to say that this year's team is the best roster since 1985. But it certainly feels like the 2026 Bears are much closer to being the best team in the NFC now that Simmons is in tow.

And Cowherd agrees. He believes the Bears are now among the three teams most capable of winning this season's Super Bowl.

Jeffery Simmons has changed the conversation in Chicago

Simmons, a four-time Pro Bowler, recorded a career-high 11 sacks in 2025 and has already produced four sacks through seven games this season.

Chicago surrendered its 2027 and 2028 first-round picks and a 2027 fourth-rounder to Tennessee, receiving Simmons and a 2028 fifth-round selection in return.

It's a massive investment, but one that gives defensive coordinator Dennis Allen the NFL's most dominant interior presence to complement Montez Sweat.

The Bears are 5-2, with Caleb Williams and Ben Johnson leading an offense that already feels like it can compete for a Super Bowl. All this team needed was a defensive game-changer to really put it over the top.

Now, they have one.

Comparing Simmons to White and Donald is aggressive. Both are among the greatest defensive players in league history, and Simmons still has plenty to prove before entering that conversation.

But Cowherd's larger point remains.

For the first time in years, the national conversation surrounding the Bears isn't about rebuilding or simply making the playoffs. It's about winning the Super Bowl.