“Jim will be missed because he does a great job and is always classy. When I first started as head coach in 1989, he was always very supportive. He has produced not only some top teams, but some of the best players in Massachusetts have come out of his program. Thanksgiving (vs. Xaverian) won’t be the same without Jim going against (Hawks’ head coach) Charlie Stevenson.”
Former Prep standout Rich McNeil went on to play football and compete in track at Bates College, and reminds O’Leary fondly. He is now finishing graduate school at Springfield College and will get a degree in athletic administration, and is also a graduate associate track coach.
“Some of the things coach O’Leary instilled in his players prepared me to do well at the next level. He laid the foundation for what I’m doing now and set the tone with his message to work hard all the time,” McNeil said. “He was always willing to put himself out there, knowing St. John’s kids want to go on to the next level. He promoted all his athletes and helped them get to that next level, even if they weren’t the best on the team.
“Being an athletic director takes a whole lot of time and effort these days. I know it can’t be easy for him to give up the coaching job, though, because he always put so much into it.”
Mike Geaslen quarterbacked the Prep football team last season and said O’Leary’s love for the game stands out.
“He cares for the team and all the players on it so much,” said Geaslen, who will play baseball at Northeastern University. “Football is his passion, and I know he’ll always be around to help out.
“The way he ran our practices was special. They weren’t the longest, but we got the most out of them because he did the same things we were going to do in games.”