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Windows: When do the Leafs have their best shot at a Cup?

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A simplified look into the future.

NHL: Stanley Cup Playoffs-Washington Capitals at Toronto Maple Leafs Tom Szczerbowski-USA TODAY Sports

The Leafs could have won the Cup this year.

I’m serious. Of course, so could any number of other teams, and a bunch of them had a much better chance than Toronto did. But there was nonetheless a chance. Hell, the Sens were an overtime goal away from the Finals, and they’re not even good. Luck goes a long way in the playoffs.

The key thing is maximizing your chances. And while the Leafs are clearly hoping to contend year-in, year-out, there are going to be circumstances that make it easier or harder to compete in a given season. Let’s go through and see when those are.

2017-18

Pros: Potentially, JVR and Bozak; improvement from the youth while still mostly on ELCs

Cons: Defence very much under construction; team was middling last year

Let’s look away from contracts, trade pressures, roster limits, and so on for a moment. Have you thought about how ridiculous this forward group is? The Leafs took a top-five offence and added Patrick freakin’ Marleau to it. Kadri and Bozak may not match their career years, but on the other hand, Matthews, Nylander and Marner are still very much on the upswing. If the Leafs decide to ride with their current F group, they could compete with Pittsburgh for the highest-scoring team in the league.

The flipside: the Leafs were a middling team last year and, while we might think they have a lot more to give, they still had a defence so porous it brought them a ways down. The Leafs should improve next year, but if they’re going to progress to being a real top five team and thus a top contender, that defence has to get a hell of a lot better. I’m not sure Ron Hainsey’s going to be enough.

2018-19

Pros: One more year of ELCs from Matthews and Marner; Lupul, Komarov, JVR, and Bozak potentially open up lots of cap space;

Cons: Those forwards may be missed

The Leafs should be--and I think are—thinking of this as a clear opening to contend. The forward lineup is going to have some turmoil as we replace some or all of the vets, but the Leafs will have a year and some cap room to use it, and they’ll have an awful lot of players who should be nearing or not far from their peaks.

The final year of a star’s ELC has been a fruitful year for previous winners. Hawks won in the final year of Toews and Kane’s ELCs (2010), while the Penguins won in the final year of Evgeni Malkin’s (2009.) Obviously a lot is riding on what the Leafs do with the rest of their money, and it gets tricky with the upcoming crunch (since Matthews and Marner will join Nylander in making a spectacular amount of money after this season.) Still, the Leafs can hopefully exploit this to the hilt; they’ve got a base here and will have resources.

2019-2020

Pros: We ought to have multiple young stars near-peak, which is nice, if you think about it; Hainsey contract off the books, if that matters

Cons: No more stars on ELCs, unless Liljegren blooms; Marleau now 40; Jake Gardiner is either gone or more expensive

Here comes the cap crunch. This is not to say I think Toronto is going to be up a creek; there should be some nice talent on the roster. But MNM will probably be making a combined salary in the mid-$20M range, and that’s going to have consequences. This is about the point where we’re going to have an idea how well Mark Hunter’s drafting has really gone for the Leafs, because we’re really going to want some inexpensive players to fill out the roster.

If the Leafs can do that—and, if Liljegren makes some hay, boy would that be spiffy—they can be competitive this year. If not, well, improvement will be tough to add in free agency.

2020-2021

Pros: Nathan Horton’s contract finally over; Marleau’s contract over

Cons: There’s gonna be a lockout and we might as well accept that now

Projecting the cap at this point starts getting fuzzy, because there seems a very good chance that there’s going to be a new CBA this year and it could do all sorts of things to alter the contract situation. But it’s worth noting that the Leafs have been careful to avoid significant salary commitments. They’re not paying anyone more than $5M as of right now; MNM will break that, but they’ve avoided tying up long-term cap room, and Marleau’s deal being three years facilitates that. A younger option might have been preferable, but also would have tied up cap room into the next decade.

Putting the best spin on a lockout—hopefully it doesn’t wipe out the whole season—the Leafs might come out of it with more options to exploit their financial clout. I don’t think the league is seriously going to move towards a luxury tax model, but anything that loosens the constraints on rich teams would be huge for the rich kids of the neighbourhood.

2021 and Beyond

Pros: The Kessel retained salary finally ends; a rising cap might make room around the MNM deals

Cons: People will age

This gets into the range where nothing is predictable. But it’s worth noting that things have gotten easier for the Penguins as time as gone on, thanks to Malkin and Crosby’s salaries taking up a diminishing share of the cap. MNM will be at their peaks now, while Kadri and Zaitsev may begin to decline. If he’s still with the team, the Leafs will have a choice on Frederik Andersen.

Conclusion

The Leafs are positioned to strike now, and then to reload for the next decade. Ideally, I could see Toronto being in its best competitive position in 2019 and in 2021. Of course, whether they’re actually able to set themselves up for contention in those years, remains to be seen.