Let's try and break down the major moves the Maple Leafs made this offseason so far and rank them from best decision to worst.
John Chayka was not shy in making the changes he said he was going to make for the Maple Leafs this offseason, and thanks to a bit of a luck and some shrewd business moves, he's certainly revamped the lineup. But not every move can be a home run, so we're here to look at what was great and what could come back to haunt the team later on.
The moves that genuinely made Toronto better
Drafting Gavin McKenna
Obviously this is going to be in the tier of better moves made by Chayka. Though he got lucky, the generational talent is now his and he'll be a focal point in the offence for the next decade plus.
Getting a creative, dynamic, and exciting superstar is one thing, but McKenna brings a humble character and mentality that keeps him in check. He never gets ahead of himself and if he isn't playing well then he wants to hear it.
He had 310 points over his last three-and-a-half seasons with the NCAA, WHL, and World Juniors and his playmaking ability will be a godsend for Auston Matthews as the team looks to spark his offence one again, not to mention his insane marketability.
If there was a move that Chayka could make this offseason that was a guaranteed slam dunk, it was drafting McKenna and he made the right call despite there being questions about who would go at #1.
Acquiring Darren Raddysh in a sign-and-trade with Tampa Bay
The first real big splash that Chayka made, bringing in Raddysh is a bit of a gamble but oh boy is the payoff worth it. Yes, he's a late bloomer and there's no guarantee that he'll replicate his 70-point campaign from 2025-26, but he's also a player Toronto hasn't had in 20 years.
Raddysh has a blistering shot from the point that often hits 100 MPH and his ability to not only shoot but pass, get the puck out of his zone and run the power-play makes him a huge asset regardless of the risks. He'll give the team something they haven't had since Bryan McCabe or Pavel Kubina - a true threat from the blueline.
He's also got the passion, as he's a Toronto native and has loved the Maple Leafs since childhood. Coming over to Toronto holds a lot of personal importance to Raddysh, and he's going to have a lot of motivation heading into the season.
Raddysh had 22 goals last year including 10 on the power-play, so his inclusion alongside Auston Matthews, William Nylander, Matthew Knies, McKenna, John Tavares, Easton Cowan; he's got a ton of opportunities to get the puck.
Is $68-million a lot for Darren Raddysh? Probably, but Toronto isn't going to worry about the financial aspect so long as he brings the heat as only he can.
Signing Sergei Bobrovsky
The biggest fish in the goaltending pond was reeled in by Chayka for three-years, $21-million. Now, $7-million is a lot to pay for a guy who will be 38 when the season opens up, but this is a guy who has been remarkably durable over the past six seasons, and his current health routine is elite.
He's going to stay healthy and able to handle the workload of a 50+ game season which is going to only help Anthony Stolarz. He can't do the starter gig anymore due to his piling injury count, so having him back up the guy he won a Cup with in Florida is a pretty good idea.
This actually also as Steve Dangle put it 'gives Toronto a starter.' Not a good goalie or one who is hot, but a true bonafide starter. They had a bevy of good to great goalies but always came up against superstars like Bobrovsky, Andrei Vasilevskiy, Jeremy Swayman, Tim Thomas, Carey Price...you're never going to win against that.
So if you can't beat em, then join em. Chayka is taking a big risk on Bobrovsky but it's a necessary evil if the team truly wants to win.
The moves that were fine but not difference-makers
Signing Teddy Blueger
Now if you were to categorize this signing I would argue it's 'fine.' Now, I did have Blueger as a potential target for Toronto and he came in at a lesser cost than I imagined, but he's not necessarily a needle mover.
Blueger is the type of player you can call 'you get what you're getting.' He's reliable, he's consistent. He's not offensive, he has a defensive first mindset, is a top-tier face-off man, is fairly speedy, and going to be a key penalty killer.
That's the reliability aspect because you know you're getting 10-20 points but also 90+ hits, over a 50% face-off win rate, and great PK numbers.
But he's just a bottom-six player much like the majority of signings that Chayka made, and while that aspect of the team needed a serious overhaul, Blueger is also a very similar player to Colton Sissons and Nick Paul; two others Toronto acquired on July 1.
He's going to be good for his role, but please don't expect him to score 20 goals, it's unreasonable.
Signing Brandon Duhaime
Again, I would classify this as a 'fine' signing though has a bit more upside given Duhaime's age, physicality and speed. He's someone who is going to hit hard, hit a lot, and provide a lot of key forechecking to keep the pressure high.
He's also a great penalty killer much like Blueger and Sissons, but again he's not a needle mover and this is purely to shore up the bottom-six to make them tougher, faster, and harder to play against.
He also comes in at a $7.8-million deal over three years which isn't terrible given the rising cap, but it feels like more of a Brad Treliving-esque signing where he tossed a bunch of money at a big guy in the hopes of toughening the team (though he's not 38, so that's a plus).
This isn't a move that will haunt Toronto unless he falls off a cliff and doesn't give the team any defensive help, but it's not a spectacular signing either. It's perfectly fine and serves its purpose - no harm, no foul.
The moves that could come back to bite them
Signing Colton Sissons (for a lot more than expected)
Now, I am going to live and die on this hill: I love Colton Sissons. I've been wanting the Maple Leafs to bring him in for the better part of a decade now because he plays a no-nonsense, tough, defensively savvy style that balances out the team.
He's elite in the face-off dot, he's a fantastic penalty killer, he's physical and a big body, can add some secondary scoring when needed and he's one of the faster players last season. But the issue here isn't signing him because it was sorely needed; it's the cost.
Sissons signed for two-years, $8.5-million contract which is a pretty hefty price increase. His last deal was for seven-years, $20.02-million ($2.68 AAV) and prior to that he was in the <$1-million threshold for AAV. This contract is a 60% increase over his previous one and it's a bit of an overpayment considering they got similar players for cheaper.
This is not a bad signing per se, but the money makes a lot of people recoil though with an ever-rising cap it's probably best to get used to this as the new normal.
Trading Dennis Hildeby for Nick Paul
Now we come to a very scary deal that definitely could haunt Toronto. In trying to improve up the middle and get a lot harder to play against, the team acquired Nick Paul from Tampa Bay but in doing so gave up Dennis Hildeby.
Hildeby could've been lost to waivers for nothing so the fact that Toronto got something for him is great but they also traded two picks on top of it. Paul is someone who can bring the offence and was hurt last year, but isn't that huge splash you'd expect Hildeby to bring back.
With Toronto putting their stock into Bobrovsky and Stolarz, they deemed Hildeby expendable and that's great except for when you get hurt. If Bobrovsky goes down for any reason then he'll leave a huge hole for Stolarz to fill. He's not the healthiest hen in the coop either, so if he's being asked to do a lot then he too could get hurt.
At that point you have Artur Akhtyamov who has very minimal NHL time and is expected to be a starter in a year or two, not this season. They signed Samuel Hlavaj but he's insurance to Akhtyamov in the Marlies and there's no real backup plan. They had Samuel Ersson but traded him away for a draft pick, and their prospects are nowhere near ready.
Of all the moves that John Chayka pulled off this offseason, this one comes with a lot more risks than rewards. Maybe he just got tired of seeing Paul completely torch the Maple Leafs in the postseason and decided to put an end to it one way or another. Either way? Risky.
What is the best move Toronto made this offseason?
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