The Chicago Bears’ offensive line has felt like a dumpster fire for years and years. After Ryan Pace’s offensive line fell apart the last couple of years, Ryan Poles took a long time to address the offensive line and didn’t do too much outside of Darnell Wright until Ben Johnson arrived.
Finally, in 2025, Bears fans got the offensive line they had been dreaming of. There was stability. There was talent. There was success. The Bears had one of the best offensive lines in the league. But then the playoffs
hit, and Ozzy Trapilo was hit with a catastrophic knee injury, and two months later, Drew Dalman retired.
Sometimes you wonder if Bears fans truly can’t have nice things.
We’ve already talked about the training camp battle that will happen between Garrett Bradbury and Logan Jones with the departure of Drew Dalman. Now let’s talk about the left tackle position with the injury to Trapilo.
Let’s start with Trapilo. We know the Bears are going to be without him to start the season. But there is no indication at this point as to when exactly he would return. Optimistic timetables would hope he returns in October and that this left tackle situation may only last for 6 or 7 games. More conservative timetables have him missing the entire season, or at least most of it.
On top of that, we don’t know how effective Trapilo will be and how well that knee will hold up and bend when he’s out there. It’s possible that even if Trapilo is back, he isn’t quite ready to actually be back, and he may struggle.
Without knowing exactly what Trapilo’s situation will be, it’s a safer bet to assume the conservative estimates are more accurate. If the more optimistic estimates come to fruition and Trapilo can play and play well, that’s icing on the cake and great news. But you’d rather be prepared for the worst and hope for the best.
If Trapilo is out for most of the year, it puts the Bears in a tricky situation of needing to find a solid left tackle for one season so Trapilo can take his spot back in 2027. To do that, the Bears have three potential candidates to fill in for Trapilo. Theo Benedet, Braxton Jones, and Jedrick Wills.
Let’s start with Benedet. Personally, I don’t think Benedet factors in here unless both Jones and Wills are disasters. Benedet was the break-glass in case of emergency last year after both Jones and Trapilo weren’t ready to play out of the gates, and I think he fills the same role this year. Benedet struggles to pass protection off the edge, and if we are being honest, we definitely saw the passing game come together more when Trapilo strengthened the pass protection. Also, keep in mind that after Trapilo was injured, Ben Johnson chose to bump Joe Thuney out to LT and play Jordan McFadden rather than have Benedet play in the playoffs. That’s telling.
So let’s look at what presumably are the two main candidates here: Wills and Jones.
Let’s start with Wills, who is a unique case. Wills was a top-ten pick back in 2020 and played decently for the Cleveland Browns. He was inconsistent in the run game, and there was a lot of talk about whether he loved football and had the competitive fire to do what was necessary in run blocking. His pass blocking was generally considered solid.
Wills suffered multiple injuries that caused him to basically have realignment surgery to get his lower half right and sat out the 2025 season. Does Wills have the mental fortitude to fight all the way back and try to earn a starting position? The talent isn’t the problem. If Ben Johnson and Dan Roushar can show Wills what it takes to be successful at this level and pull the talent out of him, this could be a steal of a signing. If Wills shows that he’s not that interested in fighting for a starting position and a spot on the Bears, he simply isn’t going to be here in September.
That leaves Braxton Jones, who is just kind of the default choice. Jones had been one of Ryan Poles’ best draft picks through the first three seasons of his career. Finding a starting left tackle in round 5 is nearly impossible to do, but credit Poles for doing it. Jones was solid, but injured his ankle at the end of the 2024 season and was never able to put it together in 2025.
Was the injury too much to overcome? Was he simply not strong enough? Was he struggling in the scheme? Was it all of the above? Jones certainly has questions, and the rest of the league believes that too, as he didn’t have offers beating down his door. If Jones gets back to the player he was from 2022 to 2024, the Bears will have themselves a perfectly capable left tackle who can go out and get paid in 2027 after a nice 2026.
If Jones looks like the guy from 2025, that’s not a guy Ben Johnson is going to have interest in starting on his offensive line. Perhaps that opens the door for Wills. Perhaps they go back to Benedet. Perhaps they go wild and sign Taylor Decker. Anything is possible if Jones doesn’t return to the player he was previously.
This left tackle battle is critically important for Caleb Williams and the offense. They need competency opposite Darnell Wright. They can’t have a revolving door over there that’s constantly allowing pressure and forcing Caleb Williams to play backyard football all game long. If Jones can prove he’s back, the job will be his, but if he opens the door, anything is possible.
I think Jones will be good enough to earn the job. I think he will be better than he was in 2025, but I don’t think he will be as good as the player we saw from 2022 to 2024. If that’s the case, the Bears will certainly hope that the more optimistic outlooks for Trapilo become fact and not fiction.
