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The Toronto Maple Leafs introduced John Chayka as their new general manager, following a disappointing season. During the press conference, reporter Steve Simmons criticized the front office, labeling Chayka a 'con artist' based on NHL sources.
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Maple Leafs reporter slams Toronto front office for hiring 'con artist' John Chayka during new GM's press conference originally appeared on The Sporting News. Add The Sporting News as a Preferred Source by clicking here.
The Toronto Maple Leafs officially welcomed their new general manager on Monday.
The franchise hired John Chayka, formerly the youngest NHL general manager ever in Arizona, to lead the way after missing the playoffs in 2025-26. But Chayka also brings a bit of a controversial history — and one reporter made sure to address it at the new executive's introductory press conference.
As Chayka met with the media about his new role, Toronto Sun reporter Steve Simmons called out the Maple Leafs' front office, saying he spoke to NHL sources that called Chayka a "con artist" and "salesman."
Here's a look at how Toronto's front office responded to questions over Chayka's scandalous history.
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Steve Simmons labeled John Chayka a 'con artist' based on information from NHL sources during the press conference introducing Chayka as the new GM.
John Chayka was previously the youngest general manager in NHL history while with the Arizona Coyotes before being hired by the Maple Leafs.
The Maple Leafs missed the playoffs in the 2025-26 season, prompting the need for a new general manager to lead the team.
The media, particularly reporter Steve Simmons, expressed skepticism about Chayka's hiring, questioning the front office's decision and highlighting concerns about his past.

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Chayka was officially announced as the Maple Leafs' new general manager on Sunday, with Mats Sundin also being named senior executive advisor of hockey operations. As Toronto made significant changes to its front office, the two new faces met with reporters on Monday.
However, Chayka comes to Toronto with a history of front-office controversies, including a 2021 suspension from the NHL.
Simmons, speaking to Maple Leafs CEO Keith Pelley, referred to the "due diligence" that Pelley said the team did before hiring Chayka, then offered his own research.
The reporter said he spoke to 20 different NHL sources, many of whom were "prominent names," about the Chayka hiring — and only one of them viewed it in a positive manner.
"The other 19 thought it was a sham, to be perfectly honest. Words were used like 'con artist,' 'liar,' 'salesman,'" Simmons said. "How did you come to a different conclusion than I was able to come to in a very short time?"
Pelley responded by saying: "I must have talked to different people."
Simmons then took it a step further, saying "that's it?" and that "the hockey world today is astounded by this announcement."
"We've conducted due diligence, and it was deep due diligence," Pelley said. "It was a thorough process, and I'm quite happy with where we've landed."
A few years after becoming the youngest NHL general manager ever at 26 in 2016, Chayka had an ugly exit from the Coyotes.
He abruptly resigned from the franchise in 2020, just one day before the playoffs were set to begin, with Arizona saying in a statement that he "quit on a strong and competitive team, a dedicated staff, and the Arizona Coyotes fans, the greatest fans in the NHL." At the time, Chayka reportedly had three years remaining on his contract.
Reports indicated that Chayka's relationship with the franchise had deteriorated, as he had begun exploring opportunities with other teams — and in January 2021, that was all but confirmed when NHL commissioner Gary Bettman announced a suspension through the entire 2021 calendar year for Chayka for violating the league's "conduct detrimental to the league and game" rules and breaching "his obligation to the club" by pursuing opportunities with other teams while still under contract with the Coyotes.
Additionally, in a separate case, the Coyotes were stripped of their 2020 second-round pick and 2021 first-round pick for violating the league's combine testing policy. Under Chayka, they were accused of conducting illegal pre-draft testing for more than 20 prospects from the Canadian Hockey League, allegedly putting them through physical tests, which is not permitted.
When Chayka was recently hired by the Maple Leafs, Hockey 24/7 reported that "at least one team" raised tampering concerns with the NHL as he began to fill out his staff for Toronto. That team "expressed concern to the NHL that employees under contract may have been contacted without proper permission."
The NHL didn't find any reported violations in its investigation.
Steve Simmons is a Canadian sports journalist who has been with the Toronto Sun for 38 years. He is the outlet's longest-serving sports columnist, described as "provocative and outspoken" in his bio for the Sun.
Simmons, who has covered plenty of major sports events for the Sun, was named Canada’s sports writer of the year in 2013 and was elected to the Canadian Football Hall of Fame in 2019. He's also written two hockey books, attended Western University, is from Toronto, and has also written for the London Free Press, Calgary Sun and Calgary Herald.