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Keith Pelley can’t afford to repeat this mistake with John Chayka

Keith Pelley can't afford to make the same mistake with John Chayka and Mats Sundin as he did when Brad Treliving was the general manager of the Toronto Maple Leafs.
May 4, 2026; Toronto, Ontario, CANADA;  Maple Leafs Sports and Entertainment CEO Keith Pelley answers media questions between Toronto Maple Leafs general manager John Chayka (left) and senior executive advisor Mats Sundin during an introductory news conference at Real Sports Bar and Grill. Mandatory Credit: Dan Hamilton-Imagn Images
May 4, 2026; Toronto, Ontario, CANADA; Maple Leafs Sports and Entertainment CEO Keith Pelley answers media questions between Toronto Maple Leafs general manager John Chayka (left) and senior executive advisor Mats Sundin during an introductory news conference at Real Sports Bar and Grill. Mandatory Credit: Dan Hamilton-Imagn Images | Dan Hamilton-Imagn Images

Toronto Maple Leafs CEO Keith Pelley cost Brad Treliving his job with the Maple Leafs over the course of last season, and he simply can't make the same mistakes with John Chayka and Mats Sundin next season.

According to The Athletic, Keith Pelley made an appearance in the Maple Leafs war room during last season's trade deadline. Pelley reportedly came into the room with trade return suggestions that were likely created by artificial intelligence. Heading into the trade deadline, Pelley was obviously concerned with the job former general manager Brad Treliving had done, and didn't feel he was the right person to lead the group moving forward. So instead of firing Treliving earlier, he decided to take matters into his own hands and run the trade deadline on his own.

The use of AI in Keith Pelley's suggested trades

Pelley attempted to help scouts find players and returns he thought were worthy of the deals they were making. Other NHL general managers found that Treliving was extremely difficult to work with, as they felt none of their trade discussions would get anywhere, likely due to the fact that Pelley was pushing for deals that were unrealistic and based on AI. Reports have suggested that Pelley remains hands-off with the Toronto Raptors, Toronto FC, and the Toronto Argos, but with the Maple Leafs, it tends to be a whole different story. For someone who doesn't have any experience in hockey, this seems like a terrible idea.

Pelley needs to trust his management staff

These kinds of actions caught the staff members off guard, as he came to the room with outlined trades the team should make. At some point, Pelley is going to need to trust his management group if he is not willing to hire a President of Hockey Operations. These kinds of maneuvers ultimately cost Brad Treliving his position as general manager. Do I believe Treliving is still the right person for the job, no; however, not having faith in the people you put in place is not a good feeling for anyone involved in the organization, including players.

Moving forward, if Pelley wants the Maple Leafs to achieve any success, he needs to back off and let John Chayka and Mats Sundin do their jobs. No team in all of sports can be successful if this is the direction they want to take. Chayka and Sundin are placed in this position for a reason, just as Treliving was. If you want to be a part of the picture, then you need a different position within the organization and MLSE.

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