Ever since MLSE President Keith Pelley dismissed Brad Treliving as GM of the Maple Leafs, he and the rest of the Leafs’ leadership have been abundantly clear: They fully intend to compete next season, with no plan to sell off their core of prime-aged and veteran players.
It has been obvious for months: the Leafs have not even remotely entertained the idea of moving Auston Matthews or William Nylander, yet they moved aggressively to acquire Darren Raddysh, who turned 30 in February.
I’m certainly not here to challenge this notion, but the way they conducted their business over the past couple of weeks made me pause for a second and think: Are the Leafs trying to have their cake and eat it too here? By that, I mean: Are they attempting to be competitive with the current group while also trying to build for the future more than they are letting on?
For all the talk about whether they should rebuild or try to win right now, they appear to be walking a middle ground rather than definitively choosing one path or the other. Yes, you run the risk of landing in the mushy middle, but the Leafs are in a rather unique spot with their prime-aged talent, to go along with just drafting first overall while not possessing their first-round pick in each of the next two years.
That theory was only furthered when John Chayka was asked about the week ahead with free agency opening and offered the following as part of his answer:
There are some needs we have. We will be aggressive, but we will also make sure we are not doing anything to hurt the future.
That last part certainly doesn’t sound like someone who is all-in right now, and his actions so far have made that rather clear.
Whatever you may think of Joseph Woll, he was the only goalie in the organization who had played 40-plus games in an NHL season. It’s possible they bring in more depth in net, but the prospect of running Anthony Stolarz, who has played 30-plus NHL games only once in his career, alongside two unproven NHL goalies who have combined for 29 NHL appearances between them is very real.
In return, they received what amounted to two mid-round picks and a 24-year-old defenseman who has played 107 NHL games and whom they appear to have every intention of giving an opportunity to.
That’s not a knock on Andrae—I actually rate him and noted as much when they made the trade. He is an interesting player, but he’s not exactly a proven commodity. While you couldn’t fully trust Woll, he at least gave them a baseline in net, capable of platooning more than any other current option while providing average-to-above-average NHL goaltending.
The upside here is clear: Andrae has the potential to become a top-six regular who offers mobility, and they have some young, exciting goalies in their pipeline. But these are upside plays on young players who generally come with growing pains. That is completely fine, but it’s not exactly pushing all the chips in to become true contenders.
Similarly, Chayka has already referenced considering internal center candidates, presumably Jacob Quillan, possibly Luke Haymes, or even Bo Groulx. He said, “We also feel like there are some players in our pipeline who are interesting as well. We want to make sure we are also considering internal candidates as we canvass different options.”
They should try at least one, and if they do, they could possibly trot out a lineup featuring 18-year-old Gavin McKenna, 21-year-old Easton Cowan, an inexperienced center option, and a defenseman who has played in the league but still has a lot to prove, to say nothing of a goalie with just 26 NHL games to his name in Dennis Hildeby. It’s not a full-on youth movement, but the lineup is suddenly quite young.
In fact, with a forward group featuring McKenna, Cowan, and Quillan, along with just nine veteran forwards, plus a group of six defensemen that includes Andrae and a Stolarz-Hildeby tandem in net, their average age would be 26.5—that would have ranked them as the third-youngest team in the league to start last season. That doesn’t include players like Bo Groulx or William Villeneuve, both of whom would lower that number even further.
They also traded Brandon Carlo away for two mid-round picks. Again, you can argue about Carlo’s fit and abilities, but he’s still a veteran right-shot defenseman who is a plus penalty killer and has generally been a good defender in his own end. Even if he was just on the third pairing, he could have provided serviceable minutes. Perhaps he wilted under the pressure after the trade, and he certainly did himself no favours when he stood around while Stolarz got run and Matthews suffered a Grade 2 MCL tear. Even so, they could have found a reduced role for him where he could have provided positive minutes, but they took the picks instead.
They have traded some baseline level of certainty for upside and potential. This isn’t even necessarily intended to judge it as right or wrong; it’s more to say that teams truly trying to win in the upcoming season don’t generally operate this way.
All of that led to a draft weekend where the Leafs made 10 selections—only the Los Angeles Kings drafted more players, with 11. Gavin McKenna was the headliner, but with a second-round pick and four third-rounders, they were able to make a number of interesting upside bets across all three positions within the top 85 picks of the draft.
It is a genuinely interesting haul, which we will get into in the notes below (and we have already profiled the picks player by player, for those who missed it).
But for all the talk about a rebuild or reset — and the debate about which direction this organization should go — this felt very much like a weekend where the Leafs tried not only to capitalize on the momentum of the first overall pick for their immediate roster, but also to use it as a springboard to help restock their cupboards and plan for the long-term future, rather than flipping picks for immediate fixes. Considering they have no notable UFAs next summer — and, truthfully, only one the summer afterward (you all know who it is) — along with a surplus of draft picks in 2027 already, they have rather quietly set themselves up to go in any direction they want moving forward, depending on how they perform this season and the big decision from their captain next summer.
Draft Notes
– We can firmly put the idea that teams wouldn’t trade with John Chayka to bed. He has already completed five deals, to varying degrees, which is two more than the Leafs completed all season (three). It’s already more than the organization completed all of last offseason (four, including the Mitch Marner sign-and-trade). One of the main positives we noted when Chayka was hired: he completed a lot of deals in Arizona. This is a Leafs team in need of smart trades. They are not a UFA or two away; they need to make legitimate, needle-moving trades. So far, they have attempted to, and in the case of the Raddysh move, gotten a significant one over the hump.
– There has also been some cleverness and proper asset management in Chayka’s moves. Last year, the Leafs didn’t qualify Pontus Holmberg, which drove me nuts at the time. I wrote this with no benefit of hindsight:
“In terms of asset management, it doesn’t sit well with me that they lost a 26-year-old who just signed for over $3 million (total value) on the open market for absolutely nothing. The Leafs own third-, fifth-, and sixth-round picks next year; is that enough to act like they can punt players who were paid reasonably on the open market?
It’s not a heartbreaking loss in terms of the player himself, but there’s definitely the potential that come the fall, we’re talking about a Leafs fourth line where we’re looking at a couple of different players on it and wondering why they’re there instead of Holmberg.”
Missing easy opportunities to add draft picks, if nothing else, is unacceptable. This is a player who immediately received multiple offers and got term, yet the Leafs just let him go for nothing. That is extremely poor business.
– Compare that to this past month, when the Leafs took on Samuel Ersson in the Joseph Woll–Emil Andrae trade, a goalie they had no intention of qualifying. Instead of not qualifying him and watching him walk, they flipped him for a fifth-round pick. Of course, they later traded a fifth-round pick (from a different year) for Raddysh in the sign-and-trade with Tampa Bay. So, in a roundabout way, it made them whole.
The fifth-round pick likely won’t amount to anything (and I hope we can look back on this and say I’m wrong!), but the point is about constantly coming out ahead on the extra two percent, not behind.
– It also wasn’t lost on me that the Washington Capitals traded a third-round pick for Alex Tuch’s rights. Tuch did receive $2 million more than Raddysh per year, but they were the two biggest UFAs at their respective positions, and the Leafs gave up considerably less.
– After the Leafs drafted McKenna, their next three picks all came from the CHL, and in total, five of their 10 selections were from the CHL. I think this has more to do with the changes to draft rights than any sort of CHL theme. There were 106 CHL players drafted in 2026, the highest total since 2010.
This is the first year the league’s new draft-rights rules came into play. Previously, players selected out of the CHL at age 18 or 19 who remained unsigned after two years had their rights expire on June 1. These unsigned prospects were typically eligible to re-enter the draft that summer, provided they were still under 20 years old. If they remained unsigned and were too old to be drafted again, they became unrestricted free agents.
That means someone like Ethan MacKenzie, who is turning 20 this year, would have essentially had to sign a pro contract even though he’s not particularly ready for one. Now, the Leafs will retain his rights for years while he heads to the University of North Dakota to continue developing. It’s a win-win for everyone.
– In the bigger picture, it makes it easier to draft CHL players because it gives teams more time to evaluate them before committing to a valuable standard player contract, for which there is a limit of 50 slots. Teams aren’t in the habit of burning those for no reason because they are forced into making a decision on a CHL player before he is even close to ready. Braeden Kressler, whom the Leafs signed to an ELC, is a good example. He was never remotely close.
– Retention aside, I liked the swing on MacKenzie. He was noticeable for Team Canada at the World Juniors, and he has a good shot, as evidenced by his 22 goals in 59 games. There are varying opinions on him, given that he really struggled in his draft year and only took off when he was much older than much of the league, but when you have four third-round picks as the Leafs did, you can easily justify a selection like that one.
– Only one of the Leafs’ 10 selections was listed under 6-foot-1—Gavin McKenna. Mark Leach has always been clear that he likes size, and while he didn’t draft a bunch of huge players, he also didn’t suddenly swing toward undersized, skilled players under new management. There was a clear theme of mobility and skating, though, especially with their top three defensemen selected.
– It will also be interesting to track late-round defenseman Yaroslav Fedoseyev. The Leafs traded a pick next year, one round higher, to move back up and get him. They already had another pick eight slots later. They must have known someone was about to take him (the Rangers had the next two picks back-to-back), and someone in the Leafs’ draft room must have been pounding the table for them to make that move.
– No issue with the Leafs drafting two goalies. Yes, they have two promising netminders in the AHL right now, but you can never have enough goalies in your system. Personally, I think every team should draft at least one goalie every single year. It is the hardest position to evaluate—you have to keep swinging if you want to hit a home run.
– It might sound crazy in a draft where they selected McKenna, the highest-upside forward in the class, but my only real complaint on paper is that it would have been nice to add one more notable upside forward, especially at center. Zach Olsen projects more as a bottom-six player, and they only drafted one center—Cooper Williams—who plateaued this season after a promising rookie campaign. As we can see with the Leafs right now, it is extremely difficult and expensive to acquire centers. You need to draft them, and the Leafs didn’t really do that in this class.
– Ten years ago, the Leafs drafted Auston Matthews first overall and made 10 other selections. Only Joseph Woll and Carl Grundstrom reached the NHL in any sort of full-time capacity among those picks. The year before, they drafted Mitch Marner, and among their eight other selections, only Travis Dermott became a regular NHL player for any meaningful stretch. The rest, as they say, is history.
There are some interesting players in this mix, but we have seen this before. The lack of success previously in stacking up mid-round picks really hurt the Leafs’ depth over the past decade. Hopefully, 10 years from now, it’s a different story with this group.
Onto free agency!
