Toronto Maple Leafs right wing William Nylander (88) controls the puck during an NHL game against the Los Angeles Kings, March 29, 2025, in Los Angeles.Kyusung Gong/The Associated Press
The classic Edmonton Oilers – the team between the time they got Wayne Gretzky and traded him away – lasted nine seasons. The Beatles were together for eight.
The current Toronto Maple Leafs era is about to hit eleven years. That’s how long ago they drafted William Nylander.
Eleven years is about as long as it took Alexander to conquer the known world. What have the Leafs conquered? The Atlantic Division, like that matters.
It is foolish to talk about consequences in sports – as in, if this doesn’t happen, then that will. Eras don’t end because teams are bad. They end when customers can’t be convinced to buy tickets, cable packages and merch. Until they make the mistake of finally winning a trophy, that will never happen to the Leafs. The city’s sunk costs are so high that they are no longer a fallacy.
There has never been any sense in the ‘Well, they have to change now’ conversation, because there is no fiscal downside in Toronto to sticking to the same, losing plan. So why risk it?
It’s better to call Post-Season 10.0 an inflection point. Whatever happens, no one will want to change, but not changing becomes unavoidable.
On Sunday, the Leafs begin what is, on paper, their easiest first-round match-up since they spit the bit against Montreal during COVID-19.
No offence to the Ottawa Senators, but experience counts for something. There are people in that organization who booked holidays in May because they didn’t realize it’s possible to play hockey past April. This should be simple.
Let’s say the Leafs win in six. That’s great. It prevents fans and media from dropping to the ground in a performative fit, and pushing themselves around in circles with their feet. It spares us the ‘This must be it’ debate, which isn’t really a debate. It’s more of a cry of pain.
Next up – the winner of Tampa Bay/Florida. This is the tough one. The Leafs haven’t won a second-round series since 2002. Louis St. Laurent was prime minister, and most cities in Canada were not yet electrified.
Getting to halfway through the playoffs doesn’t mean much to either Florida team, but it would be transformative in Toronto. After that, what challenge could we not half-face down together? We would be able to get the housing crisis half-solved, and half-bury the Gardiner Expressway.
I remember that conference final 23 years ago. It was greeted in this town like victory in a world war. It’s been bad for that long.
Beating Tampa/Florida gets Leafs management off the hook. Everybody gets to keep their job. Even Brendan Shanahan, who’s been in charge for those eleven years, in an umbrella organization that is methodically eliminating all its team presidents, probably gets an offer.
Then it’s on to play someone else. Let’s say it’s the Washington Capitals. That will be pandemonium. If the Leafs win that one and advance to the Stanley Cup final, everybody’s not just solid. They’re all getting raises.
Mitch Marner is getting a blowout offer. John Tavares is coming back on something close-ish to his current salary. Anthony Stolarz is being fast-tracked for Canadian citizenship. Tax-dodging signing bonuses for everyone!
Beyond that, we are into dancing naked in the streets territory. Best not to even consider it, beyond booking a refundable place outside the city if you plan on getting any sleep.
Then there’s the other direction.
If the Leafs lose to the Senators, a few things will happen. Per the usual, people will pretend to have had enough, though they haven’t. Toronto’s capacity for absorbing civic disappointment is limitless. It’s the most impressive thing about us.
An executive head becomes necessary. Since Shanahan is both the longest tenured and the only one whose contract is ending, he’ll have the plank cut out from behind him.
Unless he scores a hat trick in every game, Marner will take more blame for the loss than anyone else. That’s just the way it works in Toronto.
Once that happens, he’s about as likely to sign up for a penal league team than he is to come back here. Where does he end up? Las Vegas.
Then Tavares becomes an issue. The defrocked captain coming off what might have been the best all-round season by any Leaf. The club would be foolish not to re-sign him for a couple, three more years at something around half his current US$11-million salary, but will Tavares’ pride be able to absorb that insult? Is the convenience of not having to pack up all his crap and shlep it somewhere else worth accepting that his days as a star are over?
If the Leafs lose to the Senators, they’re down one, maybe two, core guys. Then it’s a rebuild, whether the Leafs want to call it that or not.
You know how it goes with renovations. You plan to take down one small wall, and all of a sudden the floors are being torn out. If the Leafs lose to Ottawa, odds are that inertia will pull them to a broader reconsideration of the roster. That’s the nuclear option.
The most difficult outcome to predict is what happens if the Leafs lose in the second round. I guess it depends on how they lose. If they go out on their backs in four, the Ottawa plan resumes. If they play lights out, take it to seven and are squeaked by a better team, then it may be business as usual. There may even be a way to bring Marner back, though probably not.
But for the first time in eleven, long years, the Leafs’ vibes-based planning is running into a contractual brick wall. It’s no longer possible to call doing nothing the something you’re doing. Whatever steps come next are volitional.
Which means change is here, even if it’s change to reaffirm that nothing will change for many more years to come.