PORTLAND—Rob O’Leary has only been on the job as Portland High School’s new athletic director for a couple of days, but he’s already got his priorities.
“We want to put our chests out, we’re Portland,” O’Leary said. “It’s time to take Portland back. I’m very aware of that school on the other side (of town). I’m a big rivalry guy.”
O’Leary grew up in Saugus, Mass., played hockey in college and served as an athletic director not only in his hometown, but in Winthrop, Mass., as well.
“Saugus and Peabody have one of the oldest rivalries in Massachusetts,” O’Leary said. “Winthrop-Revere is a big rivalry. I think rivalries are healthy. They bring the best out in people, but you have to have class.”
After O’Leary’s athletic director position in Saugus was reduced to a half-time position following last school year, he looked for a new position and wound up replacing Mike Connolly (who left to take the athletic director’s position at Westbrook) at one of the nation’s most storied high schools.
“I came across Portland and was intrigued,” O’Leary said. “There’s great history and tradition here.”
O’Leary, 37, also played baseball, football and golf in high school, played hockey at Tabor Academy (on a team which included the storied Travis Roy) and on an ECAC champion at New England College in Henniker, N.H., then coached baseball, hockey and girls’ tennis before becoming the athletic director in Winthrop, Mass., for three years and in Saugus for one.
In 2011, O’Leary was given an award by the Massachusetts Interscholastic Athletic Association for making the most significant contributions to his or her school, league, district or state by an administrator with five years experience or less.
While Portland High has a rich tradition in sports like football, basketball (the boys’ team is the defending Class A state champion) and baseball, O’Leary is focused on making all athletes at the school feel special.
“What needs to be done here at Portland High is keep the integrity and traditions, but market to every kid, not just the bigger sports,” O’Leary said. “I want to bring everyone together. Make the smaller sports feel as important as the larger sports. I want to bring school spirit. That smaller school atmosphere.
“I love working with the community, the kids and the coaches. I like being part of the day-by-day operations, being in the hallways, being on lunch duty. I want to let the coaches know they’ll be supported, but that they’ll be held to a higher level. I’m a different breed. I’ll hold people to my standards.”
O’Leary also wants to see Portland win its share of championships, but to do so in the right way.
“What I really look forward to is having success,” O’Leary said. “I love having fan buses and kids cheering. I like to be a champion. We have the potential to win serious championships. It’s my job to make sure we get that done. I want to win games and do it with class. There’s more to athletics than winning and losing. I expect the parents’ and fans’ behavior to mirror the kids’.”
The schools’ ancient and fierce rivalry notwithstanding, Deering athletic director Melanie Craig is looking forward to working with O’Leary.
“Rob’s previous experience as an athletic administrator, along with his passion for kids, makes him a great match for Portland High School,” Craig said. “The Deering and Portland athletic administrator roles have changed dramatically in the past few years. While we both celebrate and value our rivalry of over 100 years, it’s important that work together to bring consistency and collaboration to the table as well, as we move all students forward. Rob and I have very similar philosophies and a ‘kids first’ approach to leadership. I’m excited he has chosen to join the PPS family.”
O’Leary said that he’ll commute for the time being from Winthrop, Mass., where he lives with his wife, Andrea, and sons Colin (age 6) and Ryan (3).
Eventually, he plans to move to the Portland area and he hopes to be here a long time.
“I’m a Bulldog now,” O’Leary said. “When I put my heart and soul into something, I dive into it headfirst. I hope to be around a long, long time. I’d love to retire here. I hope I’m sitting here 20 years from now talking about my retirement.”