The Chicago Bears have to feel pretty good with how the first half of this season has played out. Assuming nothing changes, the Bears should contend for their first playoff appearance since 2020, and a big reason why is some of the decisions they made last offseason.
One of the most notable decisions was a heavy investment in the offensive line. One year after finishing 24th in Pro Football Focus’s final offensive line rankings, the Bears added veteran blockers Jonah Jackson, Joe Thuney, and Drew Dalman to the middle of a group that ranks seventh entering Week 10. But that ranking could be even higher if they had addressed the left tackle position.
Braxton Jones had been the starter for the past three years but was coming off a serious ankle injury and entering a contract year. With a new coaching staff in place, head coach Ben Johnson’s staff would have been best served by getting a long-term answer, and it led to the selection of Ozzy Trapilo in the second round of April’s draft.
Unfortunately, Trapilo hasn’t been the answer and it’s a decision that haunts them as they head into the second half.
Bears’ Left Tackle Struggles Expose Draft Miss on Ozzy Trapilo
The left tackle position has been the Bears’ weakest link throughout the 2025 season. Trapilo had a head start to claim the role while Jones recovered from his ankle injury and even took the lead in what offensive coordinator Declan Doyle dubbed the “King of the Mountain” practice during training camp. But Trapilo regressed and eventually gave the job back to Jones.
Jones appeared in six games and started four for Chicago before suffering a knee injury. Instead of Trapilo taking his place, he was moved to right tackle as the Bears turned to veteran backup Theo Benedet. While Benedet has been serviceable, he hasn’t been a brick wall, allowing 15 pressures and a sack on 208 pass-blocking snaps this season, which raises the question of what happened the Trapilo.
In hindsight, the Bears may have made a poor choice. Trapilo played right tackle in his final two seasons at Boston College and hadn’t taken a snap on the left side since 2022. His advanced age (he turned 24 on Oct. 17) also signaled he had fewer prospects than other players in the draft, perhaps lulling the Bears into thinking he could be a plug-and-play option on the left side.
Instead, Trapilo has been a disappointment. According to PFF, Trapilo has played 55 snaps this year and allowed two pressures on 32 pass-blocking snaps. While he had his best game as a pro in last week’s win over the Cincinnati Bengals, he only played eight snaps. His most extensive action came in a Week 4 win over the Las Vegas Raiders and while he managed a 59.9 grade in the running game, he logged a 29.5 pass-blocking grade, although he got praise from the coaching staff for that performance.
Perhaps Trapilo is more comfortable on the right side of the line, but that’s a problem considering the Bears already have Darnell Wright, who is the highest-graded offensive lineman on the team. Chicago also would have been better served selecting Josh Simmons in the first round, who wound up going 32nd to the Kansas City Chiefs and won their starting left tackle job coming out of training camp.
While that means they wouldn’t have taken Colston Loveland, left tackle was a position that the Bears needed to address. Instead, Chicago took Trapilo in the second round and created a big concern as they head into the second half.