Bears Betting Big on Ozzy Trapilo at Left Tackle - And the Timing Couldn't Be More Crucial
After enduring a brutal 2024 season up front, the Chicago Bears made one thing clear heading into 2025: they weren’t going to be caught short on offensive line talent again. That mindset explains why they didn’t hesitate to invest a second-round pick in Ozzy Trapilo, a towering tackle out of Boston College. And now, as the season hits its most pivotal stretch, the Bears are handing him the keys to one of the most important spots on the field - left tackle.
Let’s be honest: the line has improved, but it’s still a work in progress. Additions like veteran guard Joe Thuney and center Drew Dalman have helped stabilize things and given rookie quarterback Caleb Williams a fighting chance.
But the left tackle position? That’s been a revolving door.
Braxton Jones has battled injuries, Theo Benedet hasn’t held up under pressure, and promising rookie Kiran Amegadjie landed on injured reserve. Enter Trapilo.
The rookie has started the last two games - both Bears wins - and head coach Ben Johnson is sounding more and more like a coach ready to let the kid run with it. Johnson didn’t mince words when asked about the shift: “We're always going to play the guy that gives us the best chance to win the ballgame,” he said.
“I think he's an ascending player. He's still developing, and he's going to continue to get better.”
Translation: the training wheels are off.
A Natural Fit - Even on the “Wrong” Side
Trapilo made his name playing right tackle at Boston College, but with Darnell Wright firmly entrenched on the right side in Chicago, the Bears are asking Trapilo to make the switch to the left. That’s no small task - flipping sides on the offensive line is like learning to write with your non-dominant hand while getting shoved by 280-pound edge rushers. But the Bears are betting that Trapilo’s rare blend of size and athleticism can make the transition stick.
At 6-foot-8, Trapilo is one of the tallest linemen in the league, but he doesn’t lumber like it. He moves with surprising fluidity for a man his size - a crucial trait when you're tasked with protecting a quarterback like Caleb Williams, who thrives outside the pocket and extends plays with his legs. Trapilo’s ability to mirror defenders and stay engaged in space could be the difference between a sack and a game-changing scramble.
Trial by Fire
If the Bears are going to make a serious playoff push - and maybe even host a game in January - they’ll need Trapilo to grow up fast. The final five games of the season aren’t exactly a cakewalk.
Chicago has two upcoming matchups against Micah Parsons and the Green Bay Packers, plus a date with the 9-4 San Francisco 49ers. That’s a gauntlet of elite pass rushers and playoff-caliber defenses.
Johnson and his staff aren’t easing Trapilo in - they’re tossing him into the deep end and seeing if he can swim. And honestly, that might be the best approach.
If he can hold his own against top-tier competition down the stretch, the Bears may have found their long-term answer at left tackle. If not, well, it’s back to the drawing board in the offseason.
A Calculated Gamble
This is the kind of move that defines front offices. If Trapilo pans out, GM Ryan Poles will have turned a Top 60 pick into a cornerstone piece of the offensive line - and potentially solidified the protection around his franchise quarterback for years to come. If Trapilo can’t make the leap to the left side, it becomes a costly swing-and-miss at a premium position.
But for now, the Bears are leaning in. They’ve seen enough in practice and in back-to-back wins to believe Trapilo is trending in the right direction.
And with Williams continuing to develop, the timing couldn’t be more important. A stable blindside protector could be the final piece that takes this offense - and this team - from promising to playoff-ready.
There’s no guarantee it works. But in a league where you win by protecting your quarterback and dominating the trenches, the Bears are making a bold, calculated bet on their rookie tackle. And with December football heating up, we’re about to find out if Ozzy Trapilo is ready for the spotlight.