Already coming in with high expectations, John Chayka's biggest test may not be winning now, but how he prepares to build around Gavin McKenna.
There was a lot of pressure on John Chayka before he even made a single move for the Maple Leafs. Coming in after more than five years away from the game, his prior reputation and the circumstances surrounding his tenure with the Coyotes left fans wondering if MLSE and Keith Pelley made the right call.
While he's made some pretty solid moves thus far, they don't exactly cement him as the architect of the Maple Leafs and it doesn't guarantee he'll be here for the long haul. A lot rests on his success in the coming two seasons with Auston Matthews, but his real definitive test is going to come along the way - how he builds around Gavin McKenna.
Toronto has only prepared for the next two years
As much as the team has surrounded Auston Matthews with a win-now group of players, there's really only two years to do some work. If the team can't accomplish their goals of getting past the second round and competing for the Cup - Matthews may decide he wants to leave and that leaves Toronto without their captain.
It also completely strips down their roster. At the end of the 2027-28 season, the Maple Leafs will have 10 unrestricted free agents, and two RFA's to deal with, while also figuring out an extension for McKenna if they haven't by that point already.
By the time McKenna needs to re-sign, William Nylander will be 33, John Tavares will be nearly 40, Darren Raddysh will be 33, Morgan Rielly will be 35 (if he sticks around) meanwhile their other defenders like Jake McCabe and Chris Tanev will be in their mid-30's and nearly 40 respectively - not to mention both Anthony Stolarz and Sergei Bobrovsky will also be 35 and 40 years old.
The only real youth the team has to build around McKenna in the coming years consists of Matthew Knies, Easton Cowan, and Ben Danford. So the team would need to find a star player to help carry that load, or find a way to bring in younger players who are between 23-28 in order to supplement McKenna.
John Chayka must avoid sacrificing McKenna's window the current one
We can talk about how Chayka reportedly used fake graphs and information, or how he skirted the rules in order to get ahead of other teams prior to drafting - but the biggest black mark may be how he handles things going forward and he can only be judged now on the team he's built in Toronto.
If we see Chayka making moves next season that prove he's caring about the future - trading older players or not re-signing or extending certain players in order to give others a chance then we can safely assume that while he's invested heavily in the next two seasons, he's going to have the future's best intentions in mind.
On the flip side, this is the most talent he's ever had to work with, he's got basically unlimited resources at his disposal with MLSE, and failure now not only reflects poorly on the Maple Leafs but also Chayka - who may somehow manage to fumble things at the one-yard line.
If he doesn't properly prepare for Gavin McKenna and leaves him with only a couple of players to work with while creating a hodgepodge of a roster behind him then not only is that going to put more pressure on McKenna to be a leader straight away, but perhaps be the last straw for John Chayka.
Will this be John Chayka's last chance as an NHL GM?
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