Windy City Gridiron
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...
