The Chicago Bears are sitting pretty at 7-2, leading the NFC North as the season hits its midway point, but a quiet clock is ticking on some of their most vital pieces on the offensive line. Sports Illustrated just dropped the news that the front office has already secured extensions for four players into 2027 and beyond, showing they know how to find value. Now, it’s about paying that value before the market explodes and things get way too expensive. With Caleb Williams still on a cheap rookie deal, the front office has a prime opportunity to spend big on the players who actually make the team win.
One Sack Allowed. That’s It.
You gotta talk about Theo Benedet. This guy lost the starting left tackle competition back at camp, but when Braxton Jones suffered a season-ending injury, Benedet stepped up. And he did not panic. Through nine games, Benedet has given up just one measly sack and 18 pressures, all while keeping a solid 68.4 pass-blocking grade. In the run game, he’s ranked 19th among all tackles in the NFL, rocking a 73.3 grade. Sure, the Bears have complete authority over him as an exclusive rights free agent after this season, but waiting is just a poor strategy. A player holding the line this well, whether as a swing tackle or a full-time starter, absolutely deserves a long-term deal. Pay the man.
Jonah Jackson’s Redemption Tour Demands Its Reward
Then there’s Jonah Jackson, a redemption story the Bears absolutely have to finish. After Chicago traded for him with the Rams in 2025, his career looked like it was cooked, thanks to missing most of that season with an injury. But this season? Wow. Jackson has been particularly impressive, not allowing a single sack and ranking fourth in run-blocking grade at 85.1. He’s also fifth in overall grade at 83.1 among guards. He’s under contract for another year, sure, but he has no guaranteed money left on that deal. That makes him the perfect candidate for a long-term extension. And get this: locking him up now also drops his hefty $12.2 million cap hit for 2027. That’s a huge move for the future.
Building a Foundation Around Williams
It’s not just the big names, either. Linebacker D’Marco Jackson, who started his ascension last season as a pleasant surprise for the team, has also earned a spot on that extension list. The flexibility the Bears have because Caleb Williams is still on that cheap rookie deal means they can keep these core pieces together while he matures. Being 7-2 and sitting in first place in the NFC North is great, but solidifying that offensive line is, hands down, the smartest play they can make. This 7-2 record, first place in the NFC North, is awesome. But the bye week isn’t just for resting; it’s the perfect spot to take stock of these breakout performances. The front office knows they need to allocate resources to players who have proven their worth *in Chicago*. With Caleb Williams still on a rookie deal, keeping this offensive line locked down, especially with guys like Benedet and Jackson playing out of their minds, is the absolute smartest play they can make. Let’s see if they finish the job.
This article was created with AI assistance and published under Seattle On Tap’s editorial standards. See our Editorial Policy.
Originally reported by Yahoo Sports.
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