John Chayka faced a substantial challenge when hired by the Toronto Maple Leafs. His "to-do" list included appeasing the team's best player, finding a new coach, and reshaping a roster that had cratered during the previous season, a franchise-worst drop in points.
Many NHL observers wondered if the Leafs would "retool" or "rebuild." After two months on the job, it appears that Chayka has chosen to have his cake and eat it, too.
While a game has yet to be played, and much work remains to be done with the Maple Leafs roster, there is no doubt that over his short tenure, Chayka has demonstrated forward-thinking, progressive ideas in revamping the team.
Inside the Forward-Thinking Moves of Chayka's Early GM Tenure
NHL observers and fans alike questioned MLSE president and CEO Keith Pelley's choice of Chayka and senior advisor Mats Sundin to lead the Maple Leafs front office. The much-maligned Chayka came with a checkered past and minimal success during his previous stop in Arizona, with the Coyotes.
Most considered it a giant risk to put the future of the flagship Leafs in the duo's hands. The defeated mood around the franchise was immediately boosted by the unexpected lottery win, starting the pair's tenure off on the right foot.
Since then, the good times have continued to roll. Chayka's first major decision was hiring a new coach. After an exhaustive search, the out-of-left-field hiring of Jim Hiller was confirmed. While the jury is still out on this move, you can understand Chayka's logic behind it.
Hiller has previous head-coaching experience. He was an assistant with the Leafs earlier in his career, so he knows the demanding Toronto market. Also, he has a previous connection with many of the Maple Leafs most important players, such as Auston Matthews and William Nylander.
Chayka's first roster moves involved reshaping the team's leaky, plodding defense. He brought in puck-moving defenseman Emil Andrae and sent goaltender Joseph Woll to the Philadelphia Flyers in return.
Some questioned moving on from Woll, who many think was the Maple Leafs most talented goalie, but his track record of injuries made the transaction understandable. Plus, it alleviated a logjam of Toronto goalies, and Woll was likely to return the most assets.
A short time later, he was proactive in sending a fifth-round pick to the division rival Tampa Bay Lightning for the rights to pending UFA, and GTA product, Darren Raddysh, then quickly signed the hard-shooting defenseman to an eight-year max contract.
Raddysh was one of the top free agents of this year's class, but Chayka didn't let him hit the open market. The Leafs' GM added something the team has lacked during the Matthews-Nylander era, a threatening shot from the point. Chayka is banking on Raddysh not being a one-hit wonder, and while eight years is a risk for a player in his thirties, it was a forward-thinking move nonetheless.
At the NHL Draft in Buffalo this past weekend, Chayka continued remaking his roster. He sent goaltender Samuel Ersson, part of the return package for Woll, to the Ottawa Senators for a fifth-round pick, recouping the fifth-rounder he sent to Tampa for Raddysh.
Next, during Day 2 of the draft, Chayka sent plodding defenseman Brandon Carlo to the St. Louis Blues for two third-round draft picks. That move simultaneously freed up $4.1 million in cap space with free agency starting this week. It also removed the stench and reminder of the awful trade former GM Brad Treliving made in acquiring Carlo. Now, the organization can put that terrible move, trading away top prospect Fraser Minter to acquire Carlo, in the rearview mirror.
Unlike predecessors Treliving and Kyle Dubas, Chayka sees the value in draft picks and having a pipeline of prospects within the organization. He picked up a third-round pick as part of the Woll trade with the Flyers, then added two more third-rounders for the Carlo deal with the Blues. The Carlo deal, especially, was nice work for a player whose impact was minimal during his time in Toronto.
Chayka has also been unafraid to dangle big names like Matthew Knies and Morgan Rielly in the trade market, in hopes of seeing what other teams might offer. When proposals were not to his liking, he backed off.
Finally, Chayka didn't overthink the first overall pick of Gavin McKenna. He realized the gift the franchise had been presented with and went with the prospect who had the highest ceiling, the presumptive top choice for two years running.
While the true test will come when games are played next season, there is no denying Chayka has done fantastic work thus far in his short time with the Maple Leafs. His moves have demonstrated more progressiveness in two months than Treliving showed over two years.
The early returns on his tenure have prioritized forward-thinking roster design and aggressive asset management. If these initial progressive moves are any indication of the future, Chayka isn't just temporarily patching holes; he is actively engineering a sustainable blueprint and the hope of better days ahead for the franchise.
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