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The latest Sidney Crosby-to-Toronto rumor doesn’t make a lick of sense

Mar 18, 2026; Raleigh, North Carolina, USA;  Pittsburgh Penguins center Sidney Crosby (87) skates with the puck against the Carolina Hurricanes during the first period at Lenovo Center. Mandatory Credit: James Guillory-Imagn Images
Mar 18, 2026; Raleigh, North Carolina, USA; Pittsburgh Penguins center Sidney Crosby (87) skates with the puck against the Carolina Hurricanes during the first period at Lenovo Center. Mandatory Credit: James Guillory-Imagn Images | IMAGN IMAGES via Reuters Connect

Sidney Crosby is arguably the best hockey player of the 21st century. Over his 21 seasons in the NHL, he has racked up 654 goals and 1107 assists for 1761 points. He also has won three Stanley Cup Championships, two Art Ross Trophies, and two Hart Trophies. With how good he has been, plus him being the captain of Team Canada, there has always been an idea that he wants to play in Canada's biggest market. These rumors only increase with the Leafs hiring his personal trainer, Andy O'Brien. But these rumors do not make much sense

O'Brien and Crosby have had a relationship for years. He has been Crosby's personal strength and conditioning coach since he was a teenager. While he has worked with other star players like Nathan MacKinnon and John Tavares, his relationship with Crosby is what he is best known for. It helped O'Brien get a job within the Penguins organization. There is even a picture of them celebrating the Pens winning the Cup.

While the two are close, that does not mean Crosby will want to come to Toronto. O'Brien was also not hired to lure him here. He is a part of the organizational overhaul John Chayka has undergone. He is set to take over the Sports Performance department. His goal is to prepare players for the grueling 84-game series. Making sure everyone is taking care of themselves and preventing injuries as best they can. Something they have struggled with. This is about fixing an area of need with the best man for the job.

Sidney Crosby will not be a Leaf just because they hired his trainer

Crosby is also not the right player to bring in right now. Sure, he is still a productive player, having logged 29 goals and 45 assists for 74 points in 68 games last season. But he is also 38 years old. There are major questions about how much longer he will play and put up the numbers he does. You would also have to give the Penguins an offer they can't refuse to move him. It is a risky move that has a very good chance of blowing up in the Leafs' face.

Sure, the Leafs are going to try to compete for a playoff spot this season, but they are in the middle of a re-tool. They are looking to get younger and surround Auston Matthews and Gavin McKenna with talent that can be with them for years to come. It may take a season or two before the Leafs are ready to make a real push. It just does not make much sense to bring in an aging forward to that type of team, regardless of how good he's been.

Although it would be cool to see Crosby wear a Leafs sweater, it is not going to happen because his trainer works for the team. He is here to make the Leafs a healthier team, not lure Crosby.

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