May 30, 2023

The beginning of the end starts for the Toronto Maple Leafs

In the latest exhibit that the hockey gods come with a wicked sense of humor, the Toronto Maple Leafs are now tied for the longest streak of making the playoffs in the league. Thanks to the Washington Capitals, Pittsburgh Penguins, and Nashville Predators all heading for the cottage of the damned this season, it’s the Leafs and Boston Bruins tied at seven straight years. But ask any Leafs fan if that streak means anything more than a Stone of Shame.

These Toronto Maple Leafs, the biggest collection of star power at forward at least in the league, haven’t won a playoff series. They keep getting there, and they keep falling at the first hurdle. There is no more Sisyphean team in sports right now than Buds All Day. No team has promised so much and yet delivered so little. The difference between them and Sisyphus is that he just had to roll the same boulder up the hill. The one the Leafs are sentenced to gets heavier every April.

This time around, not only do the Leafs carry around the weight of their past failures and the desperation of a fanbase that borders on a cult in November much less April, but they’re carrying the idea that this might be it for this group. And even if they get past the obstacle that has defined them for nearly a decade now, a fourth playoff win, things won’t be the same after this. Whatever happens over the next week or two, the Leafs will pass through a plane of existence.

Looking ahead

First the brass tacks. Auston Matthews enters free agency after next season. He can sign an extension come this summer, and the good thing for the Leafs and Matthews is they basically already know the number. It’s $16.7 million, the max salary under next year’s cap of $83.5 million. Is that what Matthews will hold out for? Maybe maybe not but it’s the one that will shape any negotiation. Connor McDavid currently makes $12.5, the highest salary in the league with Artemi Panarin. When McDavid signed it, it was 15 percent of that year’s cap. 15 percent of next season’s cap would be $13.1 million. So there’s your range. The low end of that would be about a $1.5 million raise for Matthews per season.

That’s if Matthews wants to sign an extension now. Or he could wait for 2024, when the salary cap should jump up by a few million dollars, which would raise the maximum salary with it. Players like Matthew just haven’t gotten to free agency since his teammate John Tavares did, and he could engineer one of the biggest bidding wars in NHL history should he feel the need. It gets even more interesting should his hometown Arizona Coyotes get their new arena and suddenly are burdened with the responsibility to fill it in a way they never have before.

Even aside from the Matthews question, the Leafs have a ton of them for next season already. They have just 14 players signed for next year and just $7 million in cap space as of now to fill all those holes. Maybe they can crowbar Justin Holl, Jake Muzzin, and Matt Murray off the roster and fill some of those holes with kids, but not all of them. No matter what happens in these four to seven games with Tampa, the Leafs won’t look the same next year.

Of course, should it be another blue-clad balls-up, the long-discussed major trade could happen. William Nylander and Mitch Marner have seen their names thrown about to nearly every team in the league when Leafs fans start doing the autopsy, and that will only intensify should it not go their way this spring. Nylander hits free agency at the same time as Matthews. Marner the next summer. Even with a rising cap in a year’s time, is there room for all three? Would an aging Tavares suddenly become vulnerable to a toss overboard? He’s already shifted to wing at times to accommodate Ryan O’Reilly. Is he worth $11 million per as an aging winger? If Matthews plays hardball on an extension, would those phone lines open?

Another first-round loss could see both GM Kyle Dubas and coach Sheldon Keefe kicked into the nearest mud-puddle, despite producing 100-point seasons consistently. How will a new regime view this roster? Is Matthews going to feel better about sticking around amongst upheaval? These are just some of the balls that the Leafs have to juggle.

Careful what you wish for

There’s more to it on a spiritual plane for the Leafs this time. Another first-round loss almost makes it easier to do anything. The Leafs would have cover in saying that there is just something rotten within this group, rather than just being the biggest victim of hockey’s weirdness and callousness that isn’t tied to reason, and any decision or move they make has logic.

But should they put the Lightning to the sword, and they really should, then it’s something else. Now what’s the crutch? Losing to the Bruins in the second round would hardly be solace, but the Bs are the best regular season team of all time, at least according to wins and points, and if we ignore the souped-up standings system as opposed to what came before. Say the Leafs take the Bruins to six or seven tough games, and then Boston goes on to win the Cup. How far away are the Leafs then? Barely a half-step. What will the Bruins be in the future? Patrice Bergeron might not be around, maybe not David Krejčí either. And neither’s retirement would provide the Bs much cap relief to replace them. They will not be the same next year, likely. The Lightning are on the downside of their cycle. No one’s coming up on the outside fast enough to overtake the Leafs in the Atlantic. The Leafs can’t start over or even greatly change if they’re so close.

But with Matthews’s impending free agency, running it back again would somehow be even more fraught with pressure and expectation. If the first round has become the name that shan’t be spoken in the T.O., then a Cup-or-bust campaign will resemble something on the cutting room floor of Alice Through The Looking Glass. If Leafs players and fans thought they had it rough before…

The Leafs are neither up-and-coming, nor are they, or they shouldn’t be, on the downside of a window. No team has more riding on a first-round series, and it’s hard to think of any in the past that did as well. When it’s over, the Leafs will be something different. Wanting a simple playoff series victory might look pretty simple in four to seven games’ time. Or it might look like Black Death. The Leafs will never be the same.

To follow Sam’s descent into madness having to listen to John Buccigross call playoff games, follow him on Twitter @Felsgate.