[Editor-in-chief’s note: The bulk of this article was written on the day that it was announced that Toronto Maple Leafs’ prospect and 2020 15th overall selection Rodion Amirov passed away by his agent, Dan Milstein. While of course it may prompt questions of what might have been, I am electing not to include this event in my overall assessment of Toronto’s future out of respect. We here at Black Stitch Hockey extend our sincerest condolences to Amirov’s family, friends, teammates, and members of the overall hockey community affected by this tragic loss.]

In the culmination of the efforts (so far) of the home-drafted core of Auston Matthews; Mitch Marner; William Nylander; and Morgan Rielly, the 2022-23 Toronto Maple Leafs won a playoff series, beating the Tampa Bay Lightning in six games and marking the first series win by the franchise in nineteen years. They were then put away in five games by the eventual Eastern Conference champions, the Florida Panthers. The Leafs had a big change with GM Kyle Dubas leaving after the expiration of his contract for the Pittsburgh Penguins’ front office. His replacement was Brad Treliving, former GM of the Calgary Flames. Treliving’s job, at this point, is to build upon the team’s success and push them over the edge from competitive team to winners of the organization’s 14th Stanley Cup and their first since 1967, to end their NHL record Stanley Cup drought. How have the moves that Treliving made this summer positioned the team to do so? Let us take a look and make some judgments, while also examining the Leafs’ performance in the 2023 NHL Entry Draft.

The Leafs had a handful of departures in free agency this summer, which can be found here. The first addition, meanwhile, was by way of giving RW Ryan Reaves a three-year, $4.05 million deal. I am a big fan of Reaves, but I don’t really understand the long-term thinking here. Multiple years with an AAV of $1.35 million for a fighter who is on the wrong side of 30? It just doesn’t make sense to me. The follow-up additions were very good, however. We know why Tyler Bertuzzi was a popular rental for the Bruins last season. He scored 10 points in their 7 game series with Florida after putting up 16 in 21 regular season games with the Black and Gold and showed tremendous heart. The ability he adds to score and be a presence in front of the net is a great addition to their forward group at one-year, $5.5 million. Max Domi was given a one-year, $3 million contract, and is coming off of a 20-goal season and has the capacity for great offensive upside. Treliving definitely recognized the last of scoring depth that the team has is a serious issue (Bleacher Report points out that their goals-per-60-minutes was a poor 2.04 when Marner, Matthews, Nylander nor Taveres were on the ice – That shows a very top-heavy set of forwards). These two players mark a significant improvement in scoring options. D John Klingberg was also brought in to shore up options on the blue line on a one-year, $4.15 million deal. This addition is mostly positive but a bit of a mixed bag. Klingberg is still the sort of OFD that can put up 30-40 points a year (obviously, his 50-to-almost 70 point seasons of his prime years in Dallas are in the rear view mirror now, but still respectable), but the defensive metrics leave something to be desired. Obviously, there is some risk with the manner in which he plays the game where he is trying to be aggressive in counterattacking efforts and expecting players like him to be a total two-way menace is foolish, and let us further note that he played with a historically bad Anaheim team to start last year, but keep in mind that these are averages from the last three seasons and it paints a rough picture in that area. That said, while the Swede is a bit deep into his career at this point, he can still be a very good asset at maximum output. Further, it’s a one-year deal, so they’re not tethering themselves to him, and it does address the need for more top-tier puck movement and playmaking from the blueline beyond Morgan Rielly. It is also interesting thinking about Klingberg’s situation in light of the beginning of his hunt for a long-term deal last year, wherein he turned down an eight-year, $7.25 million-a-year contract offer from the Stars, perhaps unwisely. It is very likely that he missed his window, but good for the Leafs that they were able to get a great high-impact one-year likely-to-be rental. Another noteworthy addition was G Martin Jones at one-year, $875K. His numbers have been volatile over the years, but one asset he has is health. Goaltending injuries have definitely plagued the Leafs’ options at the position. It can’t hurt to have an option like Jones, who has had plenty of availability, in their rotation. G Ilya Samsonov was also awarded an extension of one-year, worth $3.55 million, in his arbitration case. I am certain that ideally, they want him to be healthy and playing at his top ability, but you never know if that’s what we’ll get from him and the rotation at large, so the Jones signing was smart. First round pick RW Easton Cowan signed his ELC on August 10th, at 3 years, $2.8 million. More on him momentarily. D Simon Benoit was further signed to a one-year, $775k deal. Additional signings can be found here.

Lastly, in extension related news, the Toronto Maple Leafs made Auston Matthews the highest paid player in the NHL, giving him a four-year deal worth $53 million (AAV: $13.25 million) that begins in 2024-25. This crossed off a big checklist item, as the career over-a-point-per-game, goal scoring machine of a former first overall pick was entering the UFA market at the end of the coming season. It is a bit of a disappointment that they were not able to get him longer term, but that is about the only demerit. The cost is manageable when you get down to it; at present, the Leafs will have a projected $34,172,000 in cap space, and the cap, as we emphasize on here often, is going to continue to rise in the coming seasons. There are some questions about other extensions on the horizon such as those of William Nylander and Mitch Marner, but as Clutchpoints notes, they will cross that bridge when they come to it, and they only have Morgan Rielly owed big money after this year so there is some flexibility as demonstrated by that and their current estimated cap space. This was a satisfying move for both sides. Matthews got the bag, but Toronto did not handcuff themselves financially while giving it to him, either (as much as they assuredly would have liked a longer deal).

The Toronto Maple Leafs only had three picks in this year’s draft. As mentioned, their 28th overall selection was used on RW Easton Cowan of the OHL’s London Knights. He is certainly a decent prospect with a fair amount of potential, but this feels like a reach. Take a look at this assessment by YouTuber TacTixHD: His teammate Denver Barkey had better offensive numbers, his only disadvantage being that he’s just a bit smaller than Cowan – but Barkey (who Christian asserts could be a potential Brad Marchand down the road in terms of overall contribution to the Flyers in his Philly report) was picked at 95th overall by the Philadelphia Flyers. Maybe Cowan can be better, but as TacTixHD points out, the value is just so much higher in the Barkey pick, and it seems as though Treliving and his team reached on this one. The team further drafted C Hudson Malinoski (of the Brooke Bandits of the AJHL, currently committed to Providence College) in Round 5 and D Noah Chadwick of the WHL’s Lethbridge Hurricanes in Round 6. Just a quiet couple of days for Toronto due to a lack of draft stock, and a day one that might raise some eyebrows.

I think Toronto made mostly pretty good moves to take the next step and compete for a Cup, while also locking down the player who has led the league in goals since entering the league for several more seasons. I wasn’t a fan of some of Treliving’s decisions, though, they are still currently over the cap, and I really do not get their first round selection, personally. With that said, I’m going to give them a B- for their offseason to this point. They may push for a Stanley Cup this year, but it’s not a gimme that they’re going to escape their very competitive conference, and this is probably the make-or-break point. I could go as far as to say that if they do not break their historic Cup drought this year, it likely will not happen for them for a long time. They have a good chance, though, and Toronto fans should be more excited about this group than just about any other one they’ve had in the memories of most of the fanbase. We’ll see just how far this core, with its pretty good additions, goes in its efforts to really challenge for hockey’s most sacred chalice.