Rob O’Leary, Portland High’s athletic director for the past six years, is stepping down to take a similar position at a high school in his home state of Massachusetts.

O’Leary confirmed Friday that is he departing, but declined to mention where he’s going until his new school announces his hiring, which he expects early next week.

After six years as the Portland High AD, Rob O’Leary is taking a position in Massachusetts. File photo

O’Leary, 43, said that while he loved his time in Portland, that ultimately the wear-and-tear of commuting, along with family concerns, helped convince him to make the change.

“It’s a new challenge and I’m excited about it,” O’Leary said. “This move is very positive for my family. The rides late at night were adding up and my kids (sons Colin and Ryan) are getting older. I want to be able to go to their practices and games.”

O’Leary is a native of Saugus, Massachusetts, who played hockey at New England College and served as an athletic director in his hometown, as well as in Winthrop, Massachusetts, before taking over at Portland High in August 2014.

O’Leary stabilized a position which had seen frequent turnover prior to his arrival. Participation numbers went up in recent years and the Bulldogs had the edge in their ancient rivalry versus Deering in many sports.


“The best six years of my life were in Portland,” said O’Leary. “It was more fun than anything else. From state championship wins and losses to the great friendships I’ve made with people like (boys’ basketball coach) Joe Russo, (boys’ soccer coach) Rocco Frenzilli, (baseball coach) Mike Rutherford and (former girls’ soccer coach) Dave Levasseur, the people who are PHS. (Assistant principal) Kim (Holmes) is like a family member to me. (Principal) Sheila (Jepson) has been great. The other (Southwestern Maine Activities Association) ADs really welcomed me. I worked with (former Deering AD) Mel (Craig) for four years. We were like oil-and-water at times, but we were also best friends.”

Holmes raved about O’Leary’s contributions to Portland High.

“Rob is dedicated, supportive and goes above and beyond for all of our students,” Holmes said. “He has done an amazing job of putting Portland on the map. To know him is to love him. He wasn’t afraid to have difficult conversations or fight for what students needed. Students respect him and know that he was there to listen or help them with whatever they needed. He will be missed.”

James Coffey, the athletic director at Falmouth High, previously worked with O’Leary in Massachusetts. “Rob brought some new ideas to Maine and he brought his big personality,” Coffey said. “He’s a coaches’ AD. He’s good to his coaches and he supports them. He works really well with the kids.”

O’Leary said he and Portland High are working out an exit strategy. He plans to remain at the school at least on a part-time basis until graduation day on Aug. 5.

Portland High’s search for a new athletic director is underway. Holmes said applications for the position will be taken through next Friday. She said Portland Public Schools will conduct interviews soon after and fill the post quickly.

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