The Leafs have very much put a lot of leverage and gave up a lot in futures to get the team to the point it's at right now. Defense is what it is heading into next year. They have 7 Defensemen signed for next season and the season after at $25.68 million. Their 3 most utilized Defensemen in the postseason were McCabe (1993 born), Rielly (1994 born) and Tanev (1989 born) and their 5th most utilized defenseman was Ekman-Larsson (1991 born) with only their 4th most utilized defenseman Carlo (1996 born) that is currently under the age of 30. With such an old defensive group, the Leafs were able to drive down their cap hits by handing out more term than you ideally would to older DMen like that. You figure you might pay for that on the backend to get excess value for the current year. So for next year, Leafs will just cross their fingers hope the aging DMen are able to hold up and perform close to as well as this year, figuring it's not very likely they play better given their relative ages. The Leafs have had consistent questions on if they have a true Number 1 Defenseman and if they can win without one. They'll likely have those same questions next year.
Goaltending is in a pretty good spot. Woll and Stolarz are signed for a combined $6.17 million, and both are coming off good seasons. Woll is signed for three more years and Stolarz is signed for one more year. Obviously you just kind of hope that they can match what they gave this season, which could in part be impacted by the defensemen. Goaltending can be a bit volatile and they likely outperformed the expectations people had for them coming in, so just a TBD there. Hope that both are healthy for next year and you can play whichever one is doing better.
Forwards are what it gets interesting. Toronto's biggest achilles heel has been their cap structure has been seriously messed up since 2019-20 by having too much money devoted to four forwards in general, and that arguably played too similarly if you buy into the "too soft" narrative. The counterpunch to this though and why they've avoided making any massive over-correction until now is that these high productive forwards are a big reason Toronto is comfortably in the playoffs and towards the top of the standings every year. No need to go into the past and what should have been done differently, looking forward, they have Matthews and Nylander signed for at least three more seasons at a collective $24.75 million. With NMCs I think they can both likely be assumed to stay.
Everyone knows John Tavares and Mitch Marner are both unrestricted free agents come July 1st. No question the same cap structure cannot be allowed to remain. Tavares is coming off a big season with 38 goals, nearly a point per game, but also turns 35 in September. We know he obviously chose to come to Toronto, has family ties and like it in the area and would likely prefer to remain with his family. Much about him re-signing or not at a "discount", but what does a "discount" mean for a player in that situation, and question for me on if he'd really be content to beg his way back to the team that stripped the C off his chest and has turned him into somewhat of a media scapegoat despite being a productive player throughout his tenure. For Marner, similar questions... they probably don't want to add a matching Matthews contract for cap structure reasons, but Marner only just turned 28 years old and had over 100 points. He likely wants to be in Toronto, but if that means a "discount" what kind of "discount" are we talking about, as even a "discount" will be a very high number. As a player in his prime, if he's not ready to beg his way back into Toronto then he very well could be walking.
Priority number 1 in offseason is likely an extension with Matthew Knies. A godsend to come out of their prospect pool and give them an immediate player you could slide into a top line role, be productive, give a different element, all while carrying an ELC contract. Now the ELC is up, so the decision becomes do you extend long-term or do you bridge? The benefits to long-term extension are that you can lock at hopefully a good rate and get rising years from him out of it for a longer time. With bridging, however, you can save a lot of money in the short-term and get a lot of excess value for the next year or two, but then he's due up again for what would likely be a bigger contract if he keeps progressing as you expect. Coming off a 29 goal, 58 point season, he won't command "superstar" money, but also won't be nothing. He is eligible for an offersheet if negotiations were to truly stall out, but has expressed interest in remaining in Toronto and not setting out on an offersheet path. If they are prioritizing this contract over not letting Marner/Tavares to walk, I expect it to be hammered out before July 1st.
Leafs have some other decisions to make with their bottom six. Max Paccioretty and Steven Lorentz are both unrestricted free agents on July 1st. David Kampf is signed for two more years at $2.4 million but could be traded after sitting out most of the Playoffs if Leafs wanted to clear some room. Their best remaining prospect Easton Cowan is graduating from Junior and his ELC will start, so they'll see if he's ready or needs some time in the AHL. Pontus Holmberg and Nick Robertson are Restricted Free Agents as well so Leafs may have to make a decision on if they consider either of those players part of the more immediate future. Robertson, turns 24, scratched most of the playoffs, could be a bit of a longshot play for a top 6 role as he's a pretty good scorer that's been buried if they are moving on from Tavares and Marner. Holmberg a bottom six Arb-eligible RFA a year away from UFA could likely be re-signed for cheap but could also just be someone they look to upgrade. Either way, Leafs have about 6 forwards to sign at the moment (8 forwards under contract for next year, which includes Ryan Reaves), so you'd expect pretty much all the movement to come from there.