Heading into training, the battle to determine who would protect Caleb Williams' blindside was on center stage. Heading into the second preseason game it was not sorted out, and if anything it was less clear as it had appeared to become a four-man battle.
It's also fair to say, with the starters playing against the Buffalo Bills on Sunday night, the pecking order in the left tackle battle would become clearer.
Incumbent Braxton Jones is the prohibitive favorite to win the job until shown otherwise. Rookie Ozzie Trapilo has been the primary challenger, with fan favorite second-year man Theo Benedet rising up recently to take first-team practice reps at left tackle. Kiran Amegadjie has faded from the competition, to the point his status to make the 53-man roster has been called into question.
Trapilo played right tackle in his final two college seasons at Boston College, but he played left tackle the season before that and the position is not totally foreign to him. However, it was notable when he saw reps as the second-team right tackle during practice heading into the game against the Bills. Head coach Ben Johnson and offensive line coach Dan Roushar both noted how he looked far more comfortable there.
Ozzie Trapilo is out of the left tackle competition after second preseason game
It was fair to assume Trapilo would not start against the Bills, and that was confirmed.
Bears starting offensive line tonight against the Bills:
— Sean Hammond (@sean_hammond) August 18, 2025
LT Braxton Jones
LG Luke Newman
C Drew Dalman
RG Jonah Jackson
RT Darnell Wright
Jones played the first two drives with the starters against Buffalo, as would've been expected going in. Who would play left tackle after that in the game felt pretty open-ended, then the second-team offensive line took the field.
Bears second-team offensive line tonight:
— Sean Hammond (@sean_hammond) August 18, 2025
LT Theo Benedet
LG Jordan McFadden
C Ryan Bates
RG Luke Newman
RT Ozzy Trapilo
Patrick Finley of the Chicago Sun-Times summed up the situation for Trapilo.
Ozzy Trapilo is playing right tackle with the second team, while Theo Benedet is at left tackle.
— Patrick Finley (@patrickfinley) August 18, 2025
Sure seems like Ozzy has lost the starting left tackle race.
Trapilo ultimately played 39 snaps against the Bills, all at right tackle.
Bears left tackle snap counts vs. Buffalo
— Courtney Cronin (@CourtneyRCronin) August 18, 2025
Braxton Jones - 14 (two drives with the starters)
Theo Benedet - 39
Kiran Amegadjie - 33
After playing 37 snaps at left tackle vs. Miami before moving over to right tackle with the twos last week, Ozzy Trapilo logged 39 snaps at RT last…
As much as it once looked like Trapilo would be a serious immediate challenger to Jones at left tackle, he is out of the mix now, barring something unforeseen. As we know, unexpected circumstances can occur, and Jones has not been a picture of durability, having missed 11 games over the last two seasons.
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Jones is also heading into a contract year, so the Bears have a future question mark at left tackle. With that in mind, Trapilo is absolutely an option to hold down one of the most important spots on the field for the Bears for years to come after this season.