So last Monday, my friend Jake called me up, all excited about some new Bear draft pick. “You’ve got to look up this Ozzy Trapilo guy,” he says. I’m like, what kind of a name is that? It sounds like a character from The Sopranos?
It turns out that Ozzy has a fantastic backstory. And the more I dig into it, the more fascinated I become with how he got here.
The Kid from Nowhere Special
Ozzy was raised in Norwell, Mass. Have you ever heard of it? Nor had I. It’s a small town where everybody knows everybody, and the biggest thrill is likely the high school football games on Friday nights.
His real journey began at Boston College High School in Boston. Three-star recruit; not the sort of ranking that has ESPN banging down your door. But this kid had something. Duke, Michigan, and Georgia Tech were among the schools throwing offers at him. That doesn’t happen by accident.
My neighbor’s kid played high school ball right around the same time, and he used to tell me that the guys who really make it aren’t always the flashiest. They’re the ones who show up every single day and just grind it out. That’s Trapilo all over.
College Days That Actually Mattered
Here’s where it gets interesting. Most kids these days go chasing after the glamorous schools, the ones you see on TV every Saturday. Ozzy? He stayed home to go to Boston College. Smart move, if you ask me.
For four years, he participated in no fewer than nine games a season. That’s not sitting on the bench collecting a scholarship; that’s being counted on. By 2024, he was starting all 12 games at right tackle and was named to the All-ACC First Team.
All-ACC First Team is huge. It’s like being the best pizza place in Brooklyn; there are so many great ones, and you’d better bring your A-game every single day.
The kid played tackle on both sides, too. Coaches love that flexibility. It’s like having a Swiss Army knife on your offensive line.
Draft Day Magic
April 2025 comes, and there is Ozzy Trapilo, taken in the 56th spot by the Chicago Bears. Second round! Money is real, expectations are real, and a chance to make something of himself in the N.F.L. is real.
I was watching the draft that night, and when they called out his name, I kind of choked up. This kid from a town nobody’s ever heard of has finally gotten to the show. His family was beside themselves, and honestly, you could feel how much it meant to them.
This season, Pro Football Focus awarded him an 80.5 pass-block grade. Those PFF guys are not ones to please, so that number actually means something. He played 36 games in college, which tells you all you need to know about his durability.
What the Bears Saw
Chicago wasn’t throwing darts at a draft board when they selected Ozzy Trapilo. They needed help on the offensive line, and this guy fits what they want. He’s got active hands, he knows how to keep pass rushers at bay, and he keeps his back flat when he’s blocking.
Sounds technical, but all it really means is that he knows how to do his job without getting beaten. In the NFL, that’s half the battle right there.
The Bears entered 2025 with question marks at left tackle. Often, the best answers come from where you least expect them. Now they have Ozzy going up against Kiran Amegadjie for that spot. Competition’s fantastic, and it makes everyone better.
The Human Touch
What I love about this whole story isn’t just the football stuff. The kid plays guitar! How’s that for breaking the mold? The kid plays guitar! Now that’s what I call breaking the mold! You have this 6-foot-7 mountain of a man who, you’d guess, could bench press a small sedan, and you discover he’s playing acoustic songs on his own time.
During the rookie minicamp, he was asked about moving to Chicago and what snacks he would take to the offensive line room, you know, things like that. He was just speaking naturally; no corporate talk, no canned answers. It’s just a regular dude who just happens to be really good at blocking people.
The Real Story Here
Hey, I’ve watched football for thirty years, and there have been hundreds of draft picks I have seen. It’s not his size or his numbers that make Ozzy Trapilo different, however; it’s his path.
This is not a five-star recruit who was a prodigy from age 12. This is a kid who worked for everything that he got. Three-star rating, stayed close to home, started low on the depth chart, and now he’s protecting NFL quarterbacks.
My old college roommate always said the best players aren’t the ones with the most talent; they’re the ones who squeeze every ounce out of what they’ve got. That’s Trapilo in a nutshell.
Also Read: What Nobody’s Telling You About Medicaid Cuts 2025
What’s Next
The kid needs to step up in a hurry. They have a young quarterback in Caleb Williams who will need protection, and the NFC North isn’t exactly known for playing patty-cake.
Ozzy’s going to move to left tackle, the blind side, where things get real in a hurry. But honestly? If you’re going to bet on someone to become that player, bet on the kid who has been disproving people his entire existence.
The timing’s perfect too. The Bears are constructing something in Chicago, and having a guy like Trapilo, who is someone who understands that nothing gets handed to you, is exactly what they need.
Bottom Line
Here’s my take: Ozzy Trapilo represents something we don’t see enough of anymore. Hard work is actually paying off. Staying loyal to your roots. Making it without all the hype and social media nonsense.
When my kids ask me what it takes to make it in sports, I’m going to tell them about this kid from Norwell, Massachusetts, who just kept showing up and doing the work until somebody noticed.
The Bears didn’t just get a second-round pick. They got a guy who’s going to earn his paycheck every single Sunday. And in today’s NFL, that’s worth its weight in gold.