Rob O’Leary has no ties to Maine. But he’s about to become well acquainted with its largest city.
O’Leary, a 37-year-old from Winthrop, Massachusetts, was hired as Portland High School’s new co-curricular athletic administrator. He had previously been the athletic director at two Massachusetts high schools: Winthrop and Saugus.
“I was intrigued by the size of Portland High,” said O’Leary. “I knew Portland High School has had some success in athletics and just needed someone to direct them and lead them to the next level. And here I am.”
O’Leary, also a former high school hockey, baseball and girls’ tennis coach, was one of more than 30 candidates for the position that was vacated when Mike Connolly moved over to the same position at Westbrook after two years at Portland.
Peter Eglinton, the chief operations officer for Portland Public Schools, said O’Leary’s experience as athletic director, especially in terms of fundraising, was vitally important.
“He has worked with programs where he had to raise significant funding from outside sources,” said Eglinton. “We’re looking forward to his ideas coming in.”
O’Leary said he decided to leave his hometown job in Saugus after the school system there made $2 million in budget cuts. His vision is to give Portland’s athletics a hometown feel.
“I want to take some of these state-of-the-art facilities that we have and make them feel like home for us,” he said. “It’s awesome that we get to use these facilities, we just need to make them our own.”
He said it is important to get fans and families to buy into the collaborative booster program that subsidizes Portland’s athletics. And he wants to promote all of Portland’s sports teams, not just the successful ones. Portland won the Class A state boys’ basketball championship last winter.
“I want it to get to the point where we become a family,” he said. “And I’m talking about the whole program, not just one or two sports. I want to market the whole program so that the people in the community come out to watch even the smaller ones, not just the successful ones.”
Eglinton said that O’Leary’s responsibilities, which include overseeing all co-curricular activities at the school, will also include working with Deering’s athletic director, Melanie Craig.
“We needed someone who can work with the other high school as well as the central office to ensure we have consistent policies and procedures across the district,” said Eglinton. “We need to work as a team to ensure the best outcome for all of Portland’s students.”
O’Leary has already met Craig and looks forward to working with her. He also already understands the Portland-Deering rivalry.
“She is going to be a big help for me,” said O’Leary. “She’s been around the city, she knows the players, the ins and outs of what we need, what we don’t need.
“Although she is our rival and I won’t tell her everything, there are things I will share. I understand the rivalry.”
O’Leary’s wife, Andrea, and two sons, Colin (6) and Ryan (3), will remain in Winthrop for now. She is an assistant principal in Massachusetts.
“They’ll be up for weekends,” said O’Leary. “And it’s really not that long of a drive for me, an hour 25 to my house.
“I’m sure there are some winter nights when it will be longer. But I’m willing to sacrifice that for my career and for Portland.”