Leahy was a junior starting at wide receiver and defensive back on the Prep’s 1997 undefeated Super Bowl champions, a squad led by future NFL players Brian St. Pierre at quarterback and Wayne Lucier on the line.
“We struggled when I was a freshman because we had a lot of young guys. That made winning the big title all the more special,” Leahy said. “(O’Leary) had the right personality for the job. It was fun to play for him, but he always expected things to be done right.
“I’ll never forget those pre-game speeches he and coach (Joe) Lovett used to give, including the poems they read. They knew how to really motivate the team.”
When Glatz stepped down as the Eagles’ football coach in 1983, he never hesitated in picking his young assistant coach, O’Leary, as his successor.
“I made a very good choice,” said Glatz. “He was always a hard worker, and when I retired there was nobody else as far as I was concerned. He’s had a lot of good years and done a very good job. Jim is very personable, likeable and open minded.”
Among the many friends O’Leary made in the coaching ranks over the years, count Masconomet’s Jim Pugh as one who likes and respects his fellow coach.
“I’ve known Jim a long time and he’s a personal friend as well as a fierce competitor,” said Pugh, whose Chieftains played St. John’s Prep in the 2008 season opener. The two have worked together with the Mass. State Football Coaches Association as well as the MIAA’s football committee. “St. John’s plays the top teams in the state year-in year-out every week of the season. They might lose a few, but they always take on the best.