Maple Leafs Called Out by Reporter for Hiring ‘Con Artist’ John Chayka As New GM

The Maple Leafs officially hired John Chayka as the team’s new general manager. | Dan Hamilton-Imagn Images

The Maple Leafs made some changes in the front office after a disappointing 2025-26 season that saw them miss the playoffs for the first time in a decade. After parting ways with GM Brad Treliving, Toronto filled the general manager vacancy by hiring John Chayka, in a move that hasn’t sat well with much of the fan base.

As the Maple Leafs announced Chayka’s hire in a press conference on Monday, Steve Simmons of the Toronto Sun didn’t hold back when questioning the team’s decision, going as far as to say that his sources have described Chayka as a “con artist,” a “salesman” and a “liar.”

“... I have been in contact with about 20 people who work in the National Hockey League... Of the 20 people I spoke to, one was supportive of John’s hiring and the other 19 thought it was a sham, to be perfectly honest. Words were used like “con artist, liar and salesman.” How did you come to a different conclusion that I was able to come to in a very short time?” Simmons asked Maple Leafs president Keith Pelley.

Steve Simmons goes at Keith Pelley for hiring John Chayka. This was something. pic.twitter.com/zSw8768sCQ

— World Hockey Report (@worldhockeyrpt) May 4, 2026

“I must have talked to different people,” Pelley responded dismissively, seemingly uninterested in giving a legitimate response to Simmons’s question. “We’ve conducted due diligence and it was deep due diligence. It was a thorough process and I’m quite happy with where we’ve landed.”

John Chayka’s checkered past

Chayka, 36, was last in the NHL as the GM for the Arizona Coyotes, who have since relocated and become the Utah Mammoth. When he was hired in 2016, he was just 26 years old, the youngest GM in NHL history. However, his time with the franchise was marred by scandals, and his exit from Arizona was highly controversial, as he quit his role just days before the team’s playoff run in 2020.

About a month after his departure, an NHL investigation determined that the Coyotes had violated the league’s combine testing policy by conducting illegal pre-draft testing on more than 20 players from the Canadian Hockey League. That violation resulted in the organization losing its first-round pick in 2021 and a second-round pick in ’20.

He was later suspended and barred from working in the NHL for the 2021 calendar year due to “conduct detrimental to the league and game” after it was revealed he was exploring opportunities with other clubs while still having three years remaining on his contract with the Coyotes.

Early on, his new chapter with the Maple Leafs hasn’t gotten off to a very promising start, either. Amid all the criticism over his hiring, allegations of tampering have already emerged. According to Hockey 24/7, at least one team raised concerns to the league alleging Chayka was contacting employees under contract with other teams as he began attempting to fill out Toronto’s coaching staff. The NHL investigated and determined that those concerns were “unsubstantiated.”

The Maple Leafs’ front office didn’t seem too interested in discussing Chayka’s checkered past when welcoming him aboard as the new GM.

The best way to describe that press conference:

Uncomfortable pic.twitter.com/J5AUm3NjQ6

— Chris Johnston (@reporterchris) May 4, 2026

The hiring of Chayka is certainly a questionable one. A team desperate to win a Stanley Cup and end its near 60-year drought would be expected to seek out a GM with a rich history of leading teams to the playoffs, making quality draft picks and executing big-time trades to enhance the team. Chayka, who hasn’t held a role in an NHL front office in five years, provides none of that experience, and has one of the more scandalous pasts in the sport. As for how the team settled on Chayka, all Pelley would say is that the team conducted “deep due diligence.”

Chayka will have plenty of work to do in order to claw his way into the good graces of the fan base, and it seems the media won’t be holding anything back in order to make his transition easier.

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