Darnell Wright is set to spend his third straight season as the Bears’ starting right tackle. A central aspect of Chicago’s offseason was a complete renovation along the interior of the offensive line, with guards Joe Thuney and Jonah Jackson being acquired via trade and center Drew Dalman arriving in free agency. 
Those moves should help Caleb Williams avoid taking as many sacks in 2025 as he did during his rookie season. Crucially, though, Chicago’s left tackle spot has been a question mark throughout the offseason. New head coach Ben Johnson has overseen an open competition through training camp and the preseason. With the team’s exhibition games in the books, no standout option has emerged.
“I think we’re going to have a starter Week 1, and we’ll go from there,” Johnson said (via ESPN’s Courtney Cronin). “I said it a few weeks ago – we feel good about the guys we have in that room. Someone’s gonna take the bull by the horns and is going to completely take over. But we’re not afraid to make a change if the performance isn’t where it needs to be.”
Incumbent Braxton Jones was fully cleared late last month after ankle surgery. That has allowed the pending 2026 free agent to work with the starters in training camp, but he has not done enough for Johnson to declare him the winner of the competition. Second-round rookie Ozzy Trapilo has had opportunities on the blindside as well as right tackle this summer. The same is also true of 2024 undrafted free agent Theo Benedet, who did not see any regular season game time last season.
The other player who has represented an option (albeit never the top one) in the left tackle contest is Kiran Amegadjie. Drafted in the third round last year, the Yale product made six appearances and one start as a rookie. Amegadjie could see time at left tackle in 2025, but general manager Ryan Poles said this week (via Scott Bair of the Marquee Sports Network) he will begin working at guard as well.
As such, Jones remains the likeliest candidate to start in Week 1. The 26-year-old has started each of his 40 games to date, but 11 missed contests across the past two seasons have proven to be an issue. A healthy slate in 2025 would be critical in determining Jones’ market value next spring. Based on Johnson’s comments, though, it is still unclear if Jones or any one other player will receive the left tackle nod throughout the campaign.
Who’s kidding who? It’s going to be Jones first then Trapilo. If an injury plague happens then the other 2. Everyone can stop the drama. Not sure what the purpose is of stretching it out. It’s not going to matter who plays where anyway if Williams doesn’t stay in the pocket or get rid of the ball on time anyway.
Can the coaches at least teach Williams how to scramble properly. So often he rolls out to the right and then does this absurd cutback to the left. It’s like he’s lost looking around for street signs. Really embarrassing to watch.