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The Maple Leafs found themselves looking for a new general manager after missing the playoffs for the first time in a decade. On Monday, John Chayka was officially introduced as the man for the job, but things got awkward during a press conference where a reporter posed a very pointed question concerning his qualifications.
More than 15 people have served as the GM for the Toronto Maple Leafs since the franchise won its last Stanley Cup in 1967, and Brad Treliving became the latest one to fail to bring that championship drought to an end when he was fired after three seasons in the wake of a campaign where the team finished with a 32-26-14 record while firmly failing to make the playoffs.
The Maple Leafs kicked off a search for a replacement that lasted a little more than a month before settling on John Chayka, who was viewed as a bit of a wunderkind when he became the youngest GM in NHL history after the Coyotes hired him at the age of 26 in 2016.
He had a fairly turbulent run that came to a controversial end in 2020, as he resigned right before Phoenix was set to resume the season that had been derailed by the pandemic in the bubble in Edmonton. The following year, he was suspended for “conduct detrimental to the league and game” for trying to land a gig with another team while still employed by the Coyotes, which came after the team lost a couple of draft picks in connection with a private scouting combine he organized.
Those issues didn’t stop the Maple Leafs from hiring him, and that move seemed to come as a surprise to plenty of people around the league based on what one reporter had to say at his introductory press conference.
Maple Leafs reporter Steve Simmons referred to Maple Leafs GM John Chayka as a “con artist” and “liar” while pressing the team’s president about his hiring
Steve Simmons is a somewhat infamous sportswriter who has covered the Maple Leafs for the Toronto Sun for close to 40 years. If you’re familiar with a certain rumor involving Phil Kessel’s love for hot dogs, you can credit the column he penned in 2015.
He also treated readers to a fairly eye-opening anecdote while writing about Chayka shortly before he was officially hired, asserting he had six computer monitors on his desk during his time with the Coyotes despite only using one, saying, “the other five, with data frozen on each screen, were nothing but show.”
On Monday, Simmons was in attendance at the press conference where Chayka was introduced as the new GM of the Maple Leafs, and he garnered plenty of attention for the question he directed at president Keith Pelley while questioning whether or not the team really did its due diligence.
Steve Simmonds’ question to Keith Pelley about John Chayka https://t.co/FQNZUMIPys pic.twitter.com/qHhsBHDzfH
— Rink Rat Report (@RinkRatReport) May 4, 2026
Simmons did not mince words, saying:
“In the past three to four days, I have been in contact with about 20 people who work in the National Hockey League, many of whom are prominent names that we would all know.
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,’ ‘salesman.’ How did you come to a different conclusion than I was able to come to in a very short time?”
Pelley initially responded by saying, “I must have talked to different people,” and added, “We’ve conducted due diligence, and it was deep due diligence. It was a thorough process, and I’m quite happy with where we landed” after Simmons said the “hockey world is astounded” by the decision to go with Chayka.
It’s hard to envy the situation he has inherited, and it will be very interesting to see how his tenure ends up playing out.