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

Despite being “from away,” it didn’t take very long for Rob O’Leary to become a dyed-in-the-wool Portland Bulldog.

Now, after six years as the Portland High School’s athletic director, O’Leary is stepping down to become the Director of Physical Education, Health and Athletics at Weymouth High School in South Weymouth, Massachusetts, in his home state.

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. “Weymouth is a large school that’s big in athletics and that was a draw for me. This move is very positive for my family, but I was torn making my decision. The rides late at night were adding up and my kids are getting older. I want to be able to go to their practices and games.”

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

O’Leary stabilized a position which had seen frequent turnover prior to his arrival. He hired coaches to rebuild programs like girls’ soccer, girls’ basketball, boys’ and girls’ hockey, girls’ lacrosse and softball and oversaw continued excellence in sports like football (three trips to the state final in his tenure), boys’ basketball (three state games, two state titles), boys’ soccer and baseball. Participation numbers went way up during O’Leary’s tenure at Portland and the Bulldogs had the edge in their ancient rivalry versus Deering in many sports.


“Stillman’s shot (a buzzer-beater from Stillman Mahan to give Portland’s boys’ basketball team an improbable upset victory at Deering in the 2019 Class AA North quarterfinals) is what Portland athletics is all about,” O’Leary said. “That was a gritty win. I’ll never forget it.

“The best six years of my life were in Portland. 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. They knew I always had their back.”

Indeed, Russo said that O’Leary’s support was one of his best attributes.

“I’m really grateful that he had the coaches’ backs, because as a coach, that’s all you can ask for,” said Russo, who has coached basketball for 30 years and volleyball for five years at Portland. “I’ve been very fortunate to have great ADs and Rob was unique. He is who he is and he doesn’t pull punches. For an outsider, he became the heartbeat of Portland High School and one of its biggest fans.”

O’Leary made a point of praising many of his peers as well.

“(Assistant principal) Kim (Holmes) is like a family member to me and my family,” said O’Leary. “(Principal) Sheila (Jepson) has been great. The other 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 is such an important part of our administrative team. 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. He is an amazing colleague, but an even better friend.”

O’Leary also served as a member of the Maine Principals’ Association ice hockey committee and most recently and perhaps most memorably, earned Internet fame with a series of workout videos meant to inspire student-athletes during the COVID-induced spring sports hiatus.

“Those videos took on a life of their own,” O’Leary said. “They started out as a way for me to motivate the kids and I’ve lost almost 40 pounds since the quarantine started.”

James Coffey, the athletic director at Falmouth High, who previously worked with O’Leary in Massachusetts, then also made the move from the Bay State to Maine, said that O’Leary brought a breath of fresh air north with him.

“Rob brought some new ideas to Maine and he brought his big personality, like we saw in his workout videos. He’s a funny, funny guy,” said Coffey, who once served as the athletic director at Winthrop High School while O’Leary taught physical education and coached baseball and hockey under him. “He’s a coaches’ AD. He’s good to his coaches and he supports them. He works really well with the kids. When the Falmouth job opened up, Rob was very helpful with my move to Maine. We’ve had an interesting AD relationship for many years.”


O’Leary said that 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, Aug. 5. Portland is actively seeking a new athletic director and according to O’Leary, there will be plenty of interest.

Whenever he officially departs for good, O’Leary knows the feeling will be bittersweet.

Excitement over starting a new job, but also sadness from saying goodbye.

He might be on the verge of becoming a Weymouth Wildcat, but it’s safe to say he’ll always be a Portland Bulldog at heart. One who made quite an impact during his six year-stint.

“The outpouring of support I got from families and most importantly, from students past and present, means the world to me,” O’Leary said. “They all gave me, a guy from Massachusetts who was rough around the edges, a chance.

“Hopefully, I’m leaving Portland High in a better spot then when I came.

Michael Hoffer can be reached at Follow him on Twitter: @foresports.

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