DERRY – If this really is Brian O’Reilly’s final football season at Pinkerton Academy—his 48th as head coach —it looks like he’ll be going out … limping.
At least, that’s how it seemed on Day 1 of the 2026 preseason, with O’Reilly pacing the field in an elongated medical boot.
“I’ve got a bad case of Achilles tendinitis,” O’Reilly said, grabbing a quick water break about two hours into the three-hour practice. “I don’t have to wear this boot, but it keeps me from running around too much, which makes me really sore afterwards. It’s called old age.”
O’Reilly turns 73 on September 27, though he could pass for a man 10 years younger. My old assistant, the late Mike Muldoon, always called O’Reilly the “always young” Dick Clark of high school coaches.
Last Friday, when local teams officially hit the field to start fall camp, was a Dick Clark day. Boot or no boot, O’Reilly was everywhere: waving his notebook, swapping out running backs, yelling for wide receivers to sharpen their routes, and insisting everything move faster and stronger.
“Why am I still here? Because I still love it,” O’Reilly said. “This is fun for me—building something from scratch, watching the boys grow day by day, game by game. And, of course, I love the competition. I love trying to win.”
But this stage of his life is a little different. Now his own kids—all in their 40s—have kids of their own, including a sophomore at Pinkerton and a five-year-old in Natick, among the five grandchildren.
“My wife Ina and I love our grandchildren,” O’Reilly said. “They’re so much fun to be around and are the most important part of our lives.”
He’s lightened his load a bit in the past six years, moving from the classroom to the athletic director’s office and, reluctantly, giving up his second-favorite sport, lacrosse.
“I didn’t really want to give up coaching lacrosse, but it cut into my then-new job as athletic director,” he said. “Most of the games are midweek, and it was just too hard to juggle with everything else.”
But football has always been his bread and butter, especially the precision and preparation—getting 70 or 80 people on the same page for four months.
Every year is different, and O’Reilly approaches each season with new goals and methods, especially on opening day.
“This year, I think we’ve got a solid team that should be there in the end,” O’Reilly said. “My focus early on is giving more attention to the backups, maybe filling a hole or two. For the most part, we’ve got an experienced group of upperclassmen. In another year, we might start Day 1 with drills or something different.”
One reason O’Reilly has stayed so long: his staff. One is a former head coach—Jon Rich, formerly at Londonderry High—and several assistants have been around for nearly four decades.
Bryon Murphy is one of those lifers, joining the staff after graduating from Plymouth State in 1981.
“Brian always puts his heart and soul into whatever he’s doing,” Murphy said. “He’s obviously smart and never leaves a stone unturned. But he was the same as a teacher. I still talk to former students who say he was their favorite. He’s not just a smart guy—he’s a great guy.”
Murphy figures the end is near for O’Reilly, and when it comes, he’s leaving too.
“What else would I do if I wasn’t here for football?” Murphy said. “I’d probably spend a little more time with family and my grandkids. But I do that anyway. I can assure you that when he leaves, I’m leaving with him.”
Pinkerton’s best player and captain this fall, Brady Spellman, has spent every autumn of his life watching Astros football with O’Reilly at the helm.
“Coach has so many years doing this and so much wisdom when it comes to football,” Spellman said. “How many state titles does he have 10 or 11? He’s the best.”
The senior will play fullback and linebacker when the season opens in three weeks.
“My fondest memories growing up were coming to games in our Derry Demons uniforms, high-fiving the players as they ran onto the field. Coach O’Reilly is the only coach I’ve ever known here. It’s been special to finally play for him.”
O’Reilly won’t make anything official about his future, but he’s leaning toward this being the last lap of a career that began in 1978, guiding Pinkerton football.
“I’m a lucky guy, and coaching this team this year is my focus,” O’Reilly said. “We’ve got a lot of work to do over the next few weeks. I’ll enjoy every day—I can guarantee you that.”
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