Is The Chaykanator Worth the Bite

Just 60 days into John Chayka’s tenure and the “sleasy cars sales man” might be winning over the Toronto Maple Leafs faithful once again. After a widely criticized hiring, John Chayka has been a breath of fresh air since he’s entered the team. Sure, some of that positive momentum is from the lottery balls and lady luck giving them “Mr. McKenna”, but John surely has definitely addressed a need that fans were hoping for, action.

Lets look at some of the moves coming up and why Toronto may or may not have made a good pick in Chayka.

June 15th, 2026 – Signed Tins Luc Koblar to a three year contract

The Norwegian Center-man currently plays in the SHL and put up 24 points. Based on the additional signings that we will discuss later on, center ice depth has been a core weakness of this team. After Matthews and Tavares, the options at centre have consisted of Max Domi and Pontus Holmberg… Yikes. I think that having the 18 year old grow into a decent center and could help the team long term. While his numbers don’t pop off the screen, a good defensive down the lineup center could bode well for them.

Overall, I would give this move a B+.

June 16, 2026 – Acquired G Sam Ersson and D Emil Andrae and a 2026 third round pick (G Jusso Ainasto) for G Joseph Woll and D Simon Benoit

Overall I don’t get this move. Woll has been inconsistent and injured but I feel like Benoit has been pretty good and it could be a lot for a 3rd round pick (which they ended up picking a goalie with anhyway) for a guy they didnt sign and a young D. I dont know how well Emil Andrae could help this team in a win now mode. I think while Matthews is in the final years of his current deal, you would want to load up with guys who are solidified top-4 defenseman and not a young guy. But time will tell if I am wrong on this.

Overall, I would give this a C.

June 19, 2026 – Sign and Trade D Darren Raddysh for a 2026 5th round pick (C Morgan Anderberg)

This is the move of the offseason for Toronto. A key weakness of the Leafs in years past has been their back end and goaltending. While last years 70 points might be an anomaly, Toronto has a guy to replace Morgan Rielly and his cap hit and can take his role as the powerplay quarterback going forward. A key flaw of the prior teams has been spending too much on their forwards and bargain-hunting. Raddysh will be physical, a true number one guy and on a sweetheart deal compared to Byram (Wooo-Nelly).

Overall, this is an A for me.

June 27, 2026 – Acquired two picks in the 3rd round (C Zach Olsen and Mans Gudmundsson) for Brandon Carlo

Brandon Carlo was abysmal to watch last year. Putting up just 7 points in 55 games was not the move for a guy who they spent a young center in Fraser Minten a 2026 1st rounder and a 2025 4th rounder to acquire. Thankfully by wining the draft lottery and it being top 10 protected, they save the humiliation of losing McKenna, but making $4.1M and only putting up 7 points is not ideal. Clearing up that cap room definitely made room for more moves this year which could improve this team.

Overall I give it a B.

July 1, 2026 – G Sergei Bobrovsky signs for 3 years at $7M per

Sergei Bobrovsky has not started under 50 games for the Florida Panthers since 2020-2021 which was because the NHL only played 56 games that year due to the Coronavirus pandemic. This stabalizing force will be huge for a team that saw 39 games played by Woll a guy they traded before this deal was made. In their division winning year Woll and Stollarz started 30 games evenly each, which was probably a huge reason for their success. Hopefully, with a more even work load Bobrovsky/Stolarz and if necessary Aktiamov (who was insane for the Marlies by the way in the Calder Cup Playoffs), should bode well for having a better year to convince Matthews Toronto is the place to be. Now that last year may be a real regression, but the 37 year old posted a 3.07 GAA despite a .877 SV %, it should be good enough to win a whole bunch of games.

Overall I give this move a B+.

Among the major moves, the Leafs made some minor moves for C/LW Nick Paul, C Colton Scissons,C Teddy Blugger, RW Jack Roslovic, all moves that make them harder to play against and faster down the middle. It seems like John Chayka around the A- to B+ range may be doing well so far, and while its still early he has sure shown he will be active to make the team win. Using stats like skating speed and intangibles like hard hitters, the team looks promising. After the narrative of a guy that no one wants to talk to in the industry, he sure is making a lot of moves to prove all the doubters wrong!