The thought was there when Ozzy Trapilo first stepped onto an NFL field for the Chicago Bears season opener against the Minnesota Vikings on Sept. 8.
“It’s always kind of in the back of my mind,” Trapilo said.
Growing up with his two older sisters in the Boston area, there was memorabilia all over his childhood home. Trapilo was nearing his third birthday when his father, Steve, died of a heart attack at age 39 in 2004. But there were memories all around him from his father’s time playing football at Boston College and in the NFL for the New Orleans Saints.
“So you kind of know,” Trapilo said. “As long as I can remember really. That was like a fundamental part of him.”
It’s now a fundamental part of Trapilo’s story too. Every step of the way he has followed in his father’s footsteps. First he went to Boston College High School, where his dad also played football. Then he followed Steve’s path down the road to Boston College.
Now he has followed his dad to the NFL too. Last spring the Bears made Trapilo a second-round selection (No. 56) in the NFL draft.
Trapilo doesn’t have any memories of his dad. He was too young when he died. But Steve’s memory lives on in the home.
“Growing up, that’s how I always knew him,” Trapilo said. “I knew he was a football player.”
‘It was nice to be home’
Every time Trapilo walked into the weight room at BC High, he saw his dad’s name. The room was named in honor of Steve, who donated a bunch of equipment in the mid-1990s.
Steve Trapilo played at the high school in the early ’80s before moving on to Boston College. In the famous clip of quarterback Doug Flutie’s Hail Mary against Miami in 1984, after throwing the 48-yard touchdown pass in the final seconds, Flutie jumps into the arms of one of his offensive linemen. That was Steve Trapilo.
Boston College offensive lineman Steve Trapilo lifts Doug Flutie after the quarterback completed a 48-yard Hail Mary touchdown pass that beat Miami as time expired on Nov. 23, 1984, in Miami. (Joe Rimkus Jr./Miami Herald)
“I don’t have many other words to describe it,” Ozzy Trapilo said of that clip. “It’s kind of surreal.”
The Saints drafted Steve in the fourth round in 1987, and he played six seasons for them. He briefly signed with the New England Patriots in 1993, but that marked the end of his playing days.
Afterward, Steve returned to BC High and became a volunteer assistant coach for the football team.
“That’s just the nature of Steve,” said Jon Bartlett, who coached with Steve Trapilo back then. “He was always looking to help BC High for what it did for him as a young man and making him the young man that he was. He credited everything to BC High and the BC High football program.”
Bartlett, now the athletic director at St. Sebastian’s School in the Boston area, coached Ozzy Trapilo at BC High when Ozzy was a sophomore. Ozzy was a “beanpole” back then, but he was tall and athletic.
He was a really good basketball player in those days too.
“You knew if Ozzy put on the weight and strength it was going to be a really impressive combination because seeing him on the court moving, running up and down the court, he was one of the fastest players on the basketball team,” Bartlett said. “Just his speed and getting up and down the court and his footwork in the post.”
That’s where the weight room came into play. Trapilo spent countless hours there, with his dad’s name on the wall providing “a little bit of extra motivation.”
When he was a junior, college football coaches who were recruiting Trapilo would show up at his basketball games to watch how he moved on the court, the lateral quickness and the speed in open space. Trapilo developed into a conference MVP basketball player.
“He was a big, strong kid who was agile,” BC High basketball coach Bill Loughnane said. “He picked up things like a sponge.”
Trapilo, of course, was an impressive football player too. His college decision was never really that difficult. As a top-100 recruit, he had offers from schools all over the country — but he never truly wanted to leave home.
“BC definitely had a leg up in that,” Trapilo said. “And alongside that, most of my family is around that area, so it was nice to be home. And everyone could come to all the games, which they did. I had a good crowd for every game. It was great.
“It’s cool sort of following the path (Steve) took, while also we’re different positions, different skill types. We’re on a different journey.”
A BC connection
Bears offensive tackle Ozzy Trapilo speaks with the media after rookie minicamp at Halas Hall on Friday, May 9, 2025, in Lake Forest. (Stacey Wescott/Chicago Tribune)
The Bears knew they needed to address the left tackle position over the offseason. Braxton Jones, who had started 40 games over the previous three seasons, was coming off ankle surgery, and questions remained about whether he was the long-term answer.
At the NFL scouting combine in February, general manager Ryan Poles promised competition at left tackle.
“That’s another spot where there’s going to be competition and you build the line with the best five guys,” Poles said at the time.
In March, the Bears made major changes on the offensive line, trading for guards Joe Thuney and Jonah Jackson and signing free-agent center Drew Dalman. But they didn’t bring in anyone at left tackle.
Their focus turned to the draft. Poles and director of player personnel Trey Koziol — former Boston College teammates themselves — found a tackle prospect they liked in a familiar place.
Trapilo was a 6-foot-8, 316-pound senior who spent his entire career at Boston College despite coaching changes and the ever-changing, transfer-crazy world of modern college football.
“Obviously (we) have a lot of touch points up there at BC,” Koziol said on draft night in April.
Bears guard Jonah Jackson (73), center Drew Dalman (52), guard Joe Thuney (62) and tackle Ozzy Trapilo (75) head to the line of scrimmage ahead of quarterback Caleb Williams (18) in the third quarter against the Packers on Dec. 7, 2025, at Lambeau Field in Green Bay. (John J. Kim/Chicago Tribune)
Poles and first-year coach Ben Johnson liked Trapilo’s combination of size, toughness and smarts. Poles, who played at Boston College from 2003-07, never met Steve Trapilo, but he certainly heard stories about him through other alumni.
“I know a lot of guys that played with him and knew him,” Poles said. “It was really cool to hear their appreciation for that connection. So just kind of one of those small-world things.”
Poles, an offensive lineman, went through training camp as an undrafted rookie with the Bears in 2008 but didn’t make the roster. He found himself in need of a job and wound up back at Boston College as a graduate assistant.
That kicked off a career that eventually would lead to his becoming Bears GM. In a strange coincidence, when Poles left Boston College for a scouting assistant job with the Kansas City Chiefs in 2009, Johnson took his old job as a BC graduate assistant for the 2009 season. Their paths were so close to crossing, yet that wouldn’t happen for another 16 years when Poles hired Johnson.
But back to 2025: Trapilo needed a little time to develop his game at the NFL level. He found himself in what became a four-way battle for the left tackle job during training camp. Jones won the starting job entering Week 1, but Johnson hinted that the decision wasn’t permanent. In October, the Bears moved to second-year tackle Theo Benedet.
Trapilo did what he always has done. He went back to work. The Bears worked him at both right and left tackle while sometimes utilizing him as a sixth offensive lineman.
“You saw his daily improvement, whether it was working left side or right side,” offensive line coach Dan Roushar said. “You just see him start to be more consistent in his play.”
‘He’s got to keep improving’
Bears left tackle Ozzy Trapilo blocks Browns defensive end Myles Garrett in the fourth quarter Sunday, Dec. 14, 2025, at Soldier Field. (Brian Cassella/Chicago Tribune)
The Bears offense stepped off the field after Cleveland Browns star pass rusher Myles Garrett sacked quarterback Caleb Williams on third down. It was Dec. 14, and the Bears were in the midst of a push for the playoffs.
Roushar took a look at the photos of the third-down play on his tablet from the team’s sideline. Trapilo had his hands on Garrett before the six-time All-Pro sneaked around him for the sack.
“Hey, you’re in good shape here. How’d you lose it?” Roushar asked Trapilo.
Before Trapilo could answer, Thuney, the veteran team captain with four Super Bowl rings, piped up.
“That’s Myles Garrett,” Thuney said.
He had a point.
“You know, I think I did OK,” Trapilo later said of his matchups against Garrett. “There’s always stuff you want back, obviously. There’s a couple plays that I look at the film and say I wish my technique was more like this.”
Garrett finished with 1½ sacks. The Bears have done a good job of not letting some of the star pass rushers on their schedule blow up games. Garrett and the Vikings’ Javon Hargrave in Week 1 are the only opponents to record more than one sack in a game.
“Ben does a really good job of understanding what we can and can’t do,” Roushar said.
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That means not leaving your rookie left tackle on an island against a player of Garrett’s caliber very often. Roushar doesn’t beat around the bush. The veteran O-line coach tells it like it is, and that’s what his players like about him. Trapilo called him “demanding, but in a good way.”
Roushar, an Iowa native who played quarterback at Northern Illinois, worked under Sean Payton and Dennis Allen in New Orleans coaching the offensive line and tight ends. He then coached two seasons at Tulane and was set to retire before Johnson called him about the Bears offensive line job.
In the secretive world of the NFL, in which it sometimes can feel like everybody is walking on eggshells in front of the media, Roushar can be refreshingly candid. Asked about his rookie left tackle, he said there’s plenty of work to be done.
“He’s got to keep improving,” Roushar said of Trapilo. “He has to be a much better run blocker. He’s got to get more consistent in pass pro, get stronger and be more physical, on and on and on. And if he could just grow a little bit in every one of those areas, we’re going to have a better football player.”
The Bears were waiting all offseason for somebody to step up at left tackle. Before emerging as the starter, Trapilo served as the sixth lineman, often coming in for jumbo packages. Trapilo found that experience rewarding because it gave him chances to see the field and opportunities to practice on both sides of the formation.
“Just getting the 10 or whatever reps per game, going out there, whatever it is, pass, run,” Trapilo said. “We kind of covered everything with that. Even motions and stuff like that. Just getting in a rhythm.”
Bears offensive tackle Ozzy Trapilo (75) blocks Steelers linebacker Nick Herbig (51) during the first quarter Sunday, Nov. 23, 2025, at Soldier Field. (Eileen T. Meslar/Chicago Tribune)
When Benedet suffered a quadriceps injury ahead of a Week 12 matchup with the Pittsburgh Steelers, the Bears inserted Trapilo into the lineup at left tackle. He has held the job since then.
The Bears have stuck with Trapilo, but as Roushar noted, there’s plenty he needs to improve on.
“He’s not going to settle for where we are now,” Trapilo said of Roushar. “He knows, he can see how much greater we can be as a unit and me as a player. So he’s out there every day hounding little things, but in the end the little things make a big difference.”
Have the Bears solved their left tackle conundrum?
That’s a question for the offseason. Right now, they are winning games and have big goals in January. The rookie left tackle is a big part of what they’re doing.
“When the season ends, then we can attack all the things that he needs to address,” Roushar said.
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