The Toronto Maple Leafs are entering a new chapter after missing the playoffs for the first time in a decade, prompting sweeping changes across the organization in an effort to end the NHL’s longest active Stanley Cup Final drought.
One of the team’s most talked-about additions this week is Sidney Crosby’s longtime performance specialist, a hire that signals Toronto is placing just as much emphasis on preparation and player development as roster construction.
The move has already generated optimism across the hockey community, with many viewing Crosby’s training model as a proven blueprint for sustained success.
Jay Rosehill Says Sidney Crosby’s Trainer Is a Big Win for Maple Leafs
Former Maple Leafs enforcer Jay Rosehill believes Andy O’Brien’s reputation speaks for itself, largely because of the years he has spent working alongside Crosby.
Appearing on Leafs Morning Take, Rosehill said Crosby’s commitment to preparation gives him confidence that Toronto made a worthwhile addition to its revamped performance department.
Reacting to O’Brien’s arrival, Rosehill said, “He looks like a different person out there. The news dumps in the summer are fun. But if you’re going to hire someone who takes care of business and doesn’t cut any corners, it would be a guy who’s been around Crosby.”
Rosehill pointed to Crosby’s relentless approach to training as the biggest endorsement possible, adding, “Sid does everything the right way. So if Sid’s name is attached to this guy, I think that’s a really good sign.”
While acknowledging he is unfamiliar with every aspect of O’Brien’s methods, Rosehill said Crosby’s influence alone carries significant credibility.
He also wondered how much the position has evolved in today’s NHL, saying, “I wonder how that job has evolved over the years, how much you have to push the players, and how much of these programs the guys do on their own.”
Even with players taking greater ownership of their offseason routines, Rosehill believes experienced performance leaders still bring meaningful value.
O’Brien arrives in Toronto with one of hockey’s strongest resumes. Beyond spending more than 20 years working with Crosby, he helped support Stanley Cup-winning teams in Pittsburgh and later served as a high-performance consultant during Florida’s back-to-back championship runs.
His responsibilities with the Maple Leafs extend well beyond strength training, as he will oversee conditioning, nutrition, sports science, injury rehabilitation, and mental performance across the organization.
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Rosehill also viewed the hire as another sign that General Manager John Chayka is thoroughly evaluating every department before the 2026-27 season.
“I’m sure if this guy just got hired by this outfit, which seems to be doing its due diligence on everyone and is bringing in a lot of different minds and hockey people, here’s another one of them,” Rosehill said.
He closed with another endorsement of O’Brien’s background, adding, “Again, I don’t know a lot about the guy, and these players are usually pretty dialed in with their own routines. But if this guy has been employed by Crosby for that type of work, and you know how seriously Sid takes it, welcome aboard.”
