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19 of 20 NHL insiders called the Chayka hire a sham and Keith Pelley’s response was seven words


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Charlie McAfee
May 4, 2026  (1:44 PM)
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MLSE CEO Keith Pelley speak to media during the introductory press conference for the hiring of John Chayka and Mats Sundin.
Photo credit: Youtube - Toronto Maple Leafs

Steve Simmons works for the Toronto Sun and he brought the heat to Keith Pelley after questioning the hiring process of John Chayka in his introductory presser.

Although he does say some egregious things from time to time, you can't deny that Steve Simmons is able to spark a debate through his articles and whether you love him or hate him; he's a name that people recognize.

Steve Simmons confronted Pelley with the most damning question of the entire press conference and the room went silent

Well, he's going to get a lot more attention now after delivering a scathing teardown of Keith Pelley's hiring of John Chayka and questioned the entire process — taking aim directly at the CEO's supposed 'due diligence':
You talk the due diligence you did prior to hiring him and now hiring him. In the past 3-4 days I have contacted 20 people in the NHL many of whom are names we all know, of all 20; 1 was supportive of his hiring, the other 19 thought it was asham, quite honestly.

Words like clown artist, liar, salesman; how did you come to a different conclusion than I did in such a short time? - Steve Simmons

Pelley was very quick to shut that down though, and added a snarky reply to Simmons' inquest:
We must have talked to different people.

That didn't sit well with the reporter, who immediately fired back and challenged Pelley to give a better answer than that:
That’s it? Because the hockey world is ASTOUNDED by this announcement.

As per usual, Pelley decided to take the corporate route with his response:
We conducted deep due diligence and I am confident in this decision.
The Toronto media themselves were stunned at the question as well; but seemed to love the passion:
Senior NHL reporter Rob Simpson also noted that those he spoke to actually responded with laughter and disbelief that Chayka was being hired; only echoing Simmons' statements:
Hmmmm. Spoke to just 4 agent/management types and got laughter/disbelief. Recall during the Arizona disaster, multiple sources weren’t at all impressed.
— This hire is a shocker.
The situation added a lot of tension in the air as Simmons asked what everyone in the room wanted to, but probably didn't want to risk asking for fear of not being viewed positively by MLSE.
But it shows a horrifying reality — Pelley and Toronto still refuse to explain their process. What was impressive about Chayka? Why did 19 other executives call it a sham? Does Neil Glasberg have blackmail on Keith Pelley and make sure he hired Chayka?
Fans are going to come away with a lot more questions than answers, and with Chayka already skirting questions about his past; it's a bad omen for the Maple Leafs.

Pelley stood firm but the gap between his confidence and the league’s reaction is the biggest question mark over this entire rebuild

So uhh, while there wasn't much said overall — it was what wasn't said that is loud and clear. Obviously Pelley wanted to avoid any distractions and did his 'due diligence' to shut down things before they got worse.
But when you have 20 executives who are actively in the league and working the rigours of a GM position and only a singular one gives a vote of confidence; you have to wonder what the issues really are.
There are 32 GMs in the NHL, and if Simmons spoke to even a third of them what would be over 10 who all said no. There were other assistants, advisors, etc. who were likely consulted as well, so it's a wide array of opinions all centred around one factor.
The question that is going to haunt Chayka and Pelley for the entire time is whether or not this was a rushed, botched, and secretive process.
He can say all he wants about due diligence, but when your new GM wants to hire the son of the guy who also just led your hiring process — it reaches nepotism of astounding proportions.
Bad start for Pelley's new entourage, and they're going to need to make sure their actions speak for the words they refused to say.
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19 of 20 NHL insiders called the Chayka hire a sham and Keith Pelley’s response was seven words

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