Maple Leafs’ Chayka Gamble Has Shades of Oilers’ Jeff Jackson Hire

The Edmonton Oilers were “accused” of hiring Jeff Jackson as the CEO of hockey operations because he had a relationship with Connor McDavid. Jackson was McDavid’s former agent, and despite not having experience as an NHL manager or head of hockey ops executive, he was given a prominent role over a much more senior and experienced executive in Ken Holland. Speculation suggested the Oilers believed having McDavid’s agent on staff would make it much easier to get McDavid to commit to a long-term deal.

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The Oilers even went so far as to hire his old coach out of Erie, Kris Knoblauch.

McDavid signed another extension with the team, but it was only a two-year deal. Some will argue the move worked, while others might contend it backfired, given that the Oilers are a worse team under the guidance of Jackson and now-GM Stan Bowman than when Holland was running things.

Still, as John Chayka rattled off the names of all of Auston Matthews‘ family members at the media conference on Monday, Toronto media started to get the sense this decision to go off the radar with the hire was no accident. It became clear that Chayka knew Matthews and his family well — Matthews grew up in Arizona, where Chayka was the GM for many years.

That’s when the pieces started seemingly fitting together.

Chayka Having an In with Matthews Doesn’t Feel Like a Coincidence

Why, of all the people who could take that high-profile and coveted job in Toronto, would the Maple Leafs choose Chayka? Given his track record is less than stellar and he hasn’t been in the NHL for years, wasn’t there a better option? Many think so, with reporter Steve Simmons even using the conference to tell MLSE CEO Keith Pelley that the people he talked to thought it a “sham” of a hire.

But, as Chayka sat there and said, “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 started to look like a person who could reach Matthews. Maybe more than most other GMs coming into the job. Pelley might believe that Chayka has Matthews’ ear. And, if he does, keeping the superstar might be more likely.

Chayka noted, “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.”

The question now is, if this is the Maple Leafs strategy — hiring a guy that Matthews has a relationship with to keep him in Toronto — does it backfire or does it help? Jeff Jackson has made some costly mistakes in Edmonton. He’s now responsible for fixing them, or McDavid will leave. That’s the risk in hiring someone who hasn’t had a track record (or at least not a strong one) as a GM or President of Hockey Ops. You can’t put someone in charge of every key decision if their only focus is on appeasing one player.

Next: Chayka Said the Right Things—But Left One Big Question Hanging