I’ve sat down to write about the past week and change in the Maple Leafs organization about a dozen times in that span, struggling to know where to start, trying not to run into tangents once started, and feeling like we were always a few hours away from yet another news piece that would change the narrative once again. At a certain point, I figured it was worth letting the dust settle for a few days and coming back later. Later is here, so largely for the sake of being able to come back to this later, let’s attack a few of the storylines one by one.
Leafs GM Search Lands on Chayka
Like a lot of people, I was pretty surprised to see that the Maple Leafs search for a hockey operations leader ended on someone that so few people expected or wanted. John Chayka has been a pretty polarizing figure across his time in the NHL, playing hard and fast when he became the GM of the Arizona Coyotes at just 26 years old, getting himself in trouble with the league multiple times, and ultimately leaving the team just before the 2020 playoffs after lying about his intentions in visiting the New Jersey Devils for stealth interview.
There were additional concerns about him being out of the league for the six years since, focusing more on the business world. There were concerns about how, despite building his reputation pre-Arizona through owning a hockey analytics business, the roster blueprint for his team never really fit the profile of applying hockey data to get wins. There’s been lots of talk of not having the right balance of ruthlessness and tact/repsect when dealing with people in his past tenure.
As people began to talk themselves into the move, defences of the Niagara-region native began to pop up. “He was young and inexperienced the first time” is a common refrain and fair. “He had to deal with Alex Meruelo as is owner” is similarly common, though only really applies to one year of his time in Arizona. A lot of talk about modern concepts he supposedly introduced to the league requires you to ignore other teams and managers having done similar before him.
I think the Leafs left a couple of robust candidates on the table in Dallas assistant GM Scott White, and former Canucks General Manager Mike Gillis. The latter was my preferred choice, as he’s had experience with repurposing struggling cores into the best possible version of themselves, and is a blend of both the old guard and the forward-thinking future. Supposedly he wasn’t told he was out of the running until the night before Chayka’s hiring was announced, so maybe that’s a good sign that the team genuinely considered a blueprint like his, which almost definitely required significant off-ice investment and restructuring.
The worry there would be if there are two contending points of view in the organization, and Chayka represented the latter. I want to give the benefit of the doubt, but can’t shake the sight of a business-speaking executive hired in an interview process led by business-speaking executives, at a time where MLSE is accused of trying to save money and generate new revenue more aggressively than they have in recent times, prioritizing dollars over W’s. We’ll get the best idea of what Toronto’s future looks like in about a month or two as the staff restructure begins – a lot of lesser-knowns are up for contract renewals, and on the flip side, many are wondering what Toronto will do with Craig Berube, who has delivered the two worst analytical Leafs seasons of the Matthews era and feels very much like a square peg trying to fit a round league, but has two years remaining on his own deal that ownership might not want to eat.
The best case scenario here is that Chayka takes his lessons learned from previous experience, combines it with more resources, and gets the team back on track in a hurry. The worst-case scenario is that the Leafs hired a GM that likely signed below market-rate due to his reputation with the intent of having him lead a corporate-first era of the team. There’s not much we can do other than wait and see, and thankfully, I think we’ll have a good idea of the organization’s lean pretty quick.
The Sundin Thing
Coming with Chayka to be a part of the Maple Leafs management structure is all-time great Mats Sundin, who returns to town on a regular basis for the first time since leaving as a player following the 2007/08 season.
Sundin’s involvement had been rumoured for weeks, with many originally assuming he was an attachment to the Gillis bid, given his time playing for Mike in Vancouver. Nope, it turns out that he knew Chayka through being mutual friends with Tie Domi, who has somehow become a pseudo-kingmaker in all this.
Sundin’s role with the team is “Senior Executive Advisor, Hockey Operations”, a title that did not exist previously, helping Chayka with “team culture, player development, and leadership support”. In other words, a lot of jargon, coming with a lot of question marks.
Many wonder if this is a PR smokescreen of sorts – a player beloved by the young adult to early-middle-age portion of the franchise to add some shine to a GM hire that wasn’t initially popular. While Sundin said he’d been keeping tabs with international hockey in his time away, his on-resume experience since leaving the game as a player is near-zero, solely including an advisory role with Sweden at the 2016 World Cup of Hockey along with three other ex-players. CEO of MLSE Keith Pelley even mentioned in the introductory press conference that Sundin didn’t even know what his title would be until the contract was placed in front of him – something said to make it seem like Mats was team-first above all else, but instead had people wondering how serious his involvement really is.
One thing I wonder about here is whether or not Sundin’s move back to Toronto is more about family than work. Specifically, his children are beginning to the age where, if they also wanted to be hockey players, the leagues and levels in which they play will begin to matter. Many of his teammates and fellow alumni have stayed in Toronto and had their kids play through the GTA loops. Two years ago, we saw Nikolai Kulemin, of the generation just after Mats, move back from Russia so his son Aleks could play his U16 year in the GTHL and get drafted into the OHL. I wonder a little if Mats is already thinking forward here and that this role is as much about having a job and residency in Ontario as it is helping the Leafs. For now, it’s nice seeing him on camera.
The Press Conference
Speaking of “nice to see Mats on camera”, he probably paid off whatever he’s being compensated with last Monday, feeling at times to be the only prepared person in the room when the new power structure was introduced to the media.
Chayka was mostly fine, but you could tell that there was an element of nerves to start, rarely looking up in reading his prepared statement and falling back on filler in the question and answer period. Pelley was often combative in his answers, perhaps not expecting to be challenged as much as he was. The reporters were about a step away from the Homer and Barney NASA press conference in The Simpsons, and we’ve all seen the Steve Simmons exchange several times over at this point.
It was a sight to behold, even if the Leafs aren’t the Toronto sports team you care most about. At Saturday’s Toronto FC game, which felt more like a cash-grab coronation for the opposing Leo Messi and Inter Miami, supports put out a “Rebuild Is Complete / Do Your Due Diligence” tifo in the south end, making reference to yet another Pelley claim that the struggling soccer team has been fixed in a Leafs press conference with the former line, and a nod to Pelley’s justifications of the hiring with the latter.
Pelley stammered and struggled mightily when Rosie Dimanno questioned how exactly the management structure is expected to work, he had a sarcastic tone when addressing Chayka’s time away from the game to Gino Reda, and when Chris Johnston attempted a much more polite version of Simmons’ question about Chayka’s prior red flags, he gave the same “due diligence” non-answer. Not a ton was asked about the team on the ice, which irritated the glass-half-full side of town, but it was interesting to see a Leafs presser where almost every question put the responder on their toes. It was like none I’d seen in recent history.
Lucky Number 12
Tuesday ended up being an extraordinary lifeline for both the on and off-ice fortunes of the hockey club. Those already uncertain by the hires were certainly not made more encouraged by Monday’s presser.
A day and a half later, a city sat glued to screens hoping that a lottery ball dispenser would make things a little better.
Toronto was in an extraordinarily unique position this year with regards to this draft lottery. For one, not a lot of people thought the team would be this deep in the mix in the first place. Even I, as someone who was “down” on the team’s fortunes for this season earlier that most, figured we were looking at an upper-mediocre team rather than one that would finish in the bottom five. Key injuries didn’t help, nor did the goaltending tandem having an even greater fall to earth than expected.
The nightmare of it all came with regards to the fate of Toronto’s draft pick, which had been promised to the Boston Bruins in a bad-on-day-one deal for Brandon Carlo at the 2024/25 Trade Deadline. Toronto only protected their pick to the Top 5, and for much of the year, it felt like they were going to send a pick in the 6-10 range to the Bruins, bringing back memories of giving the same team two Top-10 picks in 2010 and 2011.
A seven-game losing streak dragged them into 28th, but that didn’t guarantee that they’d keep their pick. Due to the possibility of teams jumping up in the draft lottery, the team still had a more-likely-than-not chance of slipping back into the range of giving Boston their draft pick.
At about 7:15 PM, the entire trajectory changed, with Toronto getting the 8.5% outcome bumping them up to 1st overall. In the 15 times a Toronto pick has been in the draft lottery (3 in another team’s possession), they have only won twice, and moved up once. Suddenly, a mistaken trade felt less catastrophic, a bad season a little less lost, and a future a little less bleak.
Toronto will almost definitely draft phenom winger Gavin McKenna with the top pick. Ivar Stenberg, a more physically mature Swedish centre, and Chase Reid, a dynamic defenceman, are both likely to make their teams very happy, and I don’t blame people for wanting to consider them. But McKenna has followed the pathway of a future superstar in every year of his trajectory, falling out of consensus favour seemingly only because of fatigue of hearing his name. This isn’t a Shane Wright scenario where all the OHL players of his draft year proved to have been hurt by losing more of the COVID season than most other regions – McKenna has continued to produce at levels with few historic comparables everywhere he’s gone.
Adding another future game-breaker, who should be at least useful right out of the gate, affords the new brass a layer of flexibility that they could only dream of in their talks a week prior. He moves most of the organization a step down the depth chart, and comes with three years of massive contract value via his entry-level deal. Adding him makes fixing other holes a lot easier, and lessens the danger of not having 2027 and 2028’s first-round picks by a fair amount.
Uncertainty With Auston Matthews
Amidst this fury of negative, positive, straight-forward and confusing news were reports about Auston Matthews and him not being sure where his future lies in Toronto. The biggest of these stories came from Chris Johnston of The Athletic a few hours before the lottery, with Elliotte Friedman adding his own notes throughout the week, most recently noting on 32 Thoughts yesterday that Matthews might want to wait until after the draft and free agency to decide what he wants to do long-term after that.
This has led to a lot of panic within the fanbase, and a lot of turning on the media for “stirring up controversy”. For those who spend any serious amount of time following the other big North American pro sports leagues, though, this isn’t hugely concerning. An example I brought up on social media over the weekend was the constant media back-and-forth between NBA star Giannis Antetokounmpo and the Milwaukee Bucks whenever one side wants more from the other. Literally as I’ve been typing this article this afternoon, an ESPN report seemed to re-open that saga for about the 50th time since 2018.
More likely than not, what we’re seeing right now is Matthews – likely through his agents or someone sympathetic to his interests in the league – trying to keep the pressure on the Maple Leafs to keep pushing to contend. What he wants specifically is anyone’s guess – it could be specific trades or signings, it could be staff changes, it could be resources, but it’s safe to say that the 28-year-old’s priority is for the team to try to dig out of this year’s hole rather than accepting it as their fate.
David Pagnotta reported today that Sundin and Chayka will be meeting with Matthews and his agent Judd Moldaver “over the next few weeks“. That doesn’t strike me as a guy who has his foot out of the door in Toronto, or he’d be getting the wheels in motion as soon as possible. My guess is for this to get to a position of concern would require Toronto to provide Matthews for an unserious long-term vision, in which case, the team will have bigger problems than losing their captain’s interest. I can understand not wanting to bend to one player’s every demand, especially if the specifics get counter-intuitive, but if it remains at an eagerness to keep spending to improve, it’s likely a good thing that the team’s all-time leading goal scorer still feels hungry to contend here.
Mitch Marner – Comeupppance Or Coincidence?
On the subject of players who did move on from the organization, a look at the top playoff scorers list will show a familiar face in a less-familiar jersey. Mitch Marner leads the league in playoff points with 16 in 10 games, including seven (a Hat Trick + 4 assists) in his last two games.
Naturally, there’s a lot of “told you so” types competing with “where was this?” types in Toronto, as Marner’s exit from Toronto came with no shortage of criticism.
I always found the timing on Marner’s reputation in to be interesting, in the sense that the market at large was very protective of him in years where there were valid reasons to be critical of his play and his working of the media. His 2019 contract negotiations were a case study in what not to do to leave a long-term impression, and from the moment he iced Game 3 against the Bruins in 2019 with a pair of blocked shots to the end of Toronto’s 3-1 collapse against Montreal in the 2021 bubble, it felt like Marner spent too much of his post-season ice time trying to win games singlehandedly, to his team’s detriment. Calling any of this out in the moment was an easy way to be accused of having a vendetta.
Marner appeared to find his playoff groove in 2022 against the Tampa Bay Lightning and generally stayed out of media trouble by that point as well, but by this point, it had become “his turn” to wear responsibly for the team’s losses, even as he was demanded to fix things he’d already fixed. Playing through the 2024 series against Boston on the after-effects of a high-ankle sprain probably didn’t help. The circumstances of his eventual departure – notably blocking a trade that would’ve given the Leafs a pivot to Mikko Rantanen at the 2024/25 trade deadline – were the salt in the wound.
It’s all a bit of a tragic mess. As for whether what he’s done this run would be possible here? I don’t see why it wouldn’t be. Anaheim and Utah of this season are weaker teams than most of Toronto’s playoff opponents in the Matthews era. Ottawa last season is probably a better comparable than all the series against Boston, Tampa, and Florida, and in that Senators series, Marner had 8 points in 6 games, only going pointless in Game 5. It also likely helps to have a blue line that knows where the offensive zone is and aspires to get there. At this point, all I’ve really got energy for here is to shrug and wish him the best.
Besides, Frederik Andersen going from The Great Elimination Game Pumpkin in his Toronto prime to Danish Patrick Roy at 36 is the more confusing ex-Leaf tour of this playoffs, for me at least.
Marlies Keep Rolling
Those who want to continue to experience playoff hockey in Toronto will have at least one more chance to see the Marlies, as they closed out their series against the Laval Rocket this weekend.
Toronto were underdogs going into their second round matchup, trailing Laval by eight standings points and a goal differential gap of 31 in the regular season. With that said, they had momentum in their season series, closing out the last two games of the regular seasons with wins against their eventual opponent, and never seemed to let a setback get to them.
The series was very back and forth. Going into the deciding game, all four games were decided by multiple goals (3-1 Laval, 6-2 Toronto, 6-2 Toronto, 4-0 Laval). I witnessed most of Toronto’s Game 3 win and while they it wasn’t their most top-down dominant affair, they took immediate advantage of Laval’s early mistakes and put the game out of reach before the first period even got to the halfway point.
Saturday at Place Bell was much more of a nailbiter, with Toronto playing from behind for most of the night. Reese Johnston picked a great time to score his first of the playoffs with fifteen minutes remaining in the third, and five minutes later, Vinni Lettieri scored the series winner, in a game where the two teams combined for just 41 shots on goal.
Toronto now take on the Cleveland Monsters in the third of what they hope will be five rounds. Toronto went 4-1-3 against Cleveland this season, with three of those losses coming in the shootout – something they won’t see in postseason action. I’ll be curious to see if Ben Danford, who comes down from the Brantford Bulldogs following the end of their OHL season, draws in on the Toronto blue line at an in this series.
For those looking to catch some of this series, Game 3 will be played at Coca-Cola Coliseum on Wednesday, May 20th, followed by a Game 4 if necessary on the 22nd. Both are 7:00 p.m. starts.
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