The Maple Leafs' struggle to answer the question of the day: Why?

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Chayka and Sundin’s introduction as the new general manager and the senior executive adviser of the Leafs, respectively, at Real Sports Bar and Grill on Monday afternoon had a bizarre and uncomfortable feel. The team tried to make things celebratory. They sat popular figures from the past — Wendel Clark, Doug Gilmour and Darcy Tucker — in reserved front-row seats and had Chayka’s young family on hand, the kids in blue Leafs jerseys with the family name on the back. Chayka said he grew up in Jordan Station, Ont., cheering for Sundin, and called it an honour to now work alongside him. Neil Glasberg — who played a “pivotal” role, according to Pelley, in a “comprehensive search” that included 27 candidates — was on hand, and so were some of the highest ranking executives of MLSE. They all cheered for Chayka and Sundin. Pelley tried to lighten the mood. He spoke glowingly about the Toronto Raptors’ playoff performance and noted that Sundin had captained the last Leafs team to make an Eastern Conference final “24 long years” ago. The president and CEO of MLSE said that when their search landed upon the ”stellar complementary hockey minds” of Chayka and Sundin, “we jumped on it,” adding for emphasis, “we jumped on it.” But Pelley didn’t go much deeper in answering the why of it all — why Chayka, with a controversial past, had landed in the top hockey operations job at a crucial time for the franchise. Asked directly why Chayka’s messy exit from Arizona — from his resignation, to forfeited draft picks in the wake of that exit, to a suspension from the league in 2021 — weren’t red flags in his hiring, Pelley offered few details in pointing to the diligence MLSE had done. “We’ve done extensive due diligence and I’m very comfortable and very confident in where we landed,” he said. Pelley said he had read “all of the reports” and talked to “numerous people” about Chayka and his background, declining to say who he spoke with. He was also unbothered by the more than five years Chayka spent outside the NHL, even when it was suggested that it might negatively affect his knowledge of the league today. “There’s still no concern from me,” Pelley said. “He knows the players in the league.” Pelley didn’t have anything to say either about Chayka’s first job as GM or what he may have been encouraged by from looking at that period with the Coyotes. He spoke instead about Chayka’s “methodical” and “measured” temperament and how “we were incredibly impressed and encouraged by John’s vision that he shared with us during the process.” Finally, he said there was no reason for the Leafs choosing for the second time in as many years not to have a president, despite this decision’s role in the team missing the playoffs for the first time in nine years. He said that this would be a “winning structure” and a “real treat.” Chayka, for his part, said he “didn’t live off the grid” for the nearly six years he was gone and remained “obsessed” with the league. He also noted the essential role of data in decision-making. “These are no longer emerging ideas,” Chayka said. “They’re essential to how elite NHL organizations operate.” It was the kind of statement that might have won over Pelley, given his stated desire for a “data-centric” GM. Chayka only kind of addressed the missteps that led him out of the league. He said there were “mistakes” that he owned. He also said he was young and didn’t value the “human connection side of things.”  Mostly, he deflected by pointing to ownership instability during his time as Arizona’s GM. He wouldn’t have that instability in Toronto, he said. “Edward Rogers brings a ton of stability, a ton of resources,” Chayka said, referring to the executive chair of Rogers Communications Inc., which owns a majority share of MLSE. “His directive to me is to win at all costs and I believe him.” Chayka did offer hints as to what winning at all costs might look like in his estimation. He said he was open to the idea of Craig Berube returning as coach (“he’s a great coach”) for one thing, and would try to sell captain Auston Matthews on the team’s ability to bounce back and compete for a Stanley Cup — that “there’s still a window here.” “It is our job to sell him on what we’re capable of in reaching the ultimate goal, because I know that that’s what’s most important to him,” Chayka said. “I think he deserves some answers about where we’re at and where we’re headed — and give him the forum to provide feedback and ask questions and then take it from there.” He didn’t detail what his version of the Leafs would look like, saying there was work to be done in assessing the situation through meetings with players. He did say the Leafs needed to defend better (either through changes to the roster or strategy) and was definitive about the team’s need to improve on defence. Sundin’s role in things, meanwhile, felt more ambiguous. The franchise great essentially said he would try to impart wisdom from the past on the team and its culture. He seemed at ease in his first day on the job, but felt more like a background player. The ones who mattered at the dawn of this new era in Toronto were Chayka and Pelley. “Nothing I say here today earns credibility in this market. That will come from how we operate,” Chayka said. We’ll soon learn what that looks like. The why of it all remains a mystery. Spot the pattern. Connect the terms Find the hidden link between sports terms