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Steve Simmons asks Keith Pelley a must-watch question Leafs fans will love

The Toronto Maple Leafs introduced John Chayka and Keith Pelley on Monday afternoon.
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

The Toronto Maple Leafs held a press conference on Monday afternoon after announcing the hiring of John Chayka as the team's new general manager and Mats Sundin as an executive advisor of sorts. And of course, it provided some wild entertainment.

While most of the questions were answered in typical fashion from two people new to the job -- Sundin talked a lot about the Leafs' team history and wanting to bring back those days, while Chayka vaguely talked about what he envisions for the team. But, easily the high point of the whole thing was when The Toronto Sun's Steve Simmons got the mic and brought some insane heat to the table.

"You talk about the due diligence that you did on John, prior to hiring him and now, hiring him. In the past, say, three to four days, I have been in contact with about 20 people who work in the National Hockey League, many of who are prominent names that we all know," Simmons said. "And of the 20 people that I spoke to, one was supportive of John's hiring, and 19 thought it was a sham, to be perfectly honest. Words were used like con artist, liar, salesman -- how did you come to a different conclusion than I was able to come to in a very short time?"

And Pelley responded extremely frank and straight forward, with an underlying fire after listening to the notorious reporter just call everything into question.

"I must have talked to different people," the MLSE CEO said.

"That's it?" Simmons responded. "Because the hockey world today is astounded by this announcement."

Pelley just had to grin and say "Okay" and repeated once again his statement that he must have talked to different people when Simmons asked for another response.

Simmons provided some high-end entertainment at introductory press conference

No matter whether you agree with the hiring of Chayka or not, Simmons just spitting out a question like that and getting the attention of the entire hockey world because of it, is so good. The Maple Leafs took a year or so off from being the true centre of the hockey universe but one hiring and one press conference later and now everyone is thinking about Toronto once again.

Simmons' reasoning for the question is clearly because Chayka does not hold a high reputation around the league. He showed some lack of experience as the youngest GM in NHL history during his tenure with the Arizona Coyotes and rubbed some more traditional people the wrong way. And, because of being the young hotshot guy who created his own private sports analytics company and didn't have any public-facing work, caused his reputation among the hockey analytics community to be questionable.

Chayka hasn't really fit in either camp of being a former player, or being a hockey analytics mind who has so much of his work in the public sphere for people to know his thoughts.

Time will tell how Chayka's full control of the Maple Leafs is going to go -- but at least it started out with a bang thanks to Steve Simmons.

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