The Chicago Bears had a banger of an offseason in 2025, going from worst to first in the NFC North Division in head coach Ben Johnson’s first year. But the second time around isn’t inspiring as much confidence.
In retrospect, some of the team’s decisions last year caught more scrutiny than was deserved and turned out better than perhaps the majority of fans and analysts expected.
Chicago paid center Drew Dalman significant money in free agency, but he turned in a Pro Bowl year. Johnson drafted tight end Colston Loveland No. 10 overall ahead of Tyler Warren, but Loveland now looks like the future of the pass game in the Windy City. Ozzy Trapilo went from a second-round pick to a viable starting left tackle in his rookie campaign.
And so on.
Thus, there are several precedents from 2025 that indicate Johnson and GM Ryan Poles deserve some grace and some time for their vision to play out this offseason. What’s more, the NFL draft hasn’t even arrived yet.
But all of that said, there is legitimate cause for concern regarding the state of the offensive line, which was the unit that saw the greatest transformation year over year, and is also the group that appears in the most danger of falling off precipitously in 2026.
Namely, Chicago’s decisions at left tackle are worthy of a raised eyebrow. After Trapilo suffered a ruptured patellar tendon in Round 1 of the playoffs, the team has re-signed Braxton Jones who battled injuries and poor play on the way to losing his starting job there last year. The Bears also signed first-round bust Jedrick Wills Jr. after he missed the entire 2025 campaign trying to get healthy.
Caleb Williams Biggest Potential Loser in Bears’ Uncertainty on Offensive Line
GettyQuarterback Caleb Williams of the Chicago Bears.
None of that bodes well for quarterback Caleb Williams as he enters Year 3 of his career.
Charlie Kravitz of “The Dominique Foxworth Show” on ESPN addressed the direness of the Bears’ situation at left tackle in regards to Williams’ development/potential regression during an April 10th edition of the program.
“That team took such a step forward last year when they were playing Ben Johnson ball and had an improved offensive line,” Kravitz said. “And they had really unfortunate circumstances with their left tackle and Dalman’s retirement at center. They have to handle that, and I know Caleb can make up for a lot of things with avoiding pressure, but you don’t want him to get into the bad habits of his rookie year.”
Bears Don’t Have Starting-Caliber Player at Left Tackle Heading into NFL Draft
GettyChicago Bears left tackle Braxton Jones.
Williams led the league with 68 sacks and 466 yards lost due to those plays during his rookie campaign. Upon Johnson’s arrival, and the subsequent improvement in the offensive front, those numbers fell to 24 sacks and 165 lost yards last season.
Jones is not the longterm answer on the left side in Chicago or Johnson wouldn’t have benched him last year, and the team wouldn’t have signed him to a paltry $5 million deal to return in 2026 after its options grew thin.
Wills, the No. 10 pick of the Cleveland Browns in 2020, played in a total of 13 games across 2023 and 2024 combined. The last time he was healthy enough to qualify for a positional ranking via Pro Football Focus was 2023, during which he finished 66th out of 84 tackles.
Theo Benedet, an undrafted player out of Canada, has 16 games of experience (eight starts) and lost the left tackle job to Trapilo during the second half of last season after taking it from Jones.
Johnson is a brilliant run-game designer and rebuilt the offensive line in one offseason, which is an incredibly difficult feat in such a short timespan. All of that earns him some credit and some trust, but the reserves of both will drain quickly if the Bears can’t protect Williams — a recent No. 1 pick who has shown flashes of greatness but is also prone to playing hero ball and making mistakes well below his talent ceiling.
Trapilo should be back before the end of 2026, but what damage his absence and the lack of a reliable replacement does before then is the biggest question facing Chicago as draft day approaches.
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