The road to the playoffs may be a slim one, but Monday was still a good day in Leafs Nation.
Not only did the Toronto Maple Leafs beat the Anaheim Ducks 5-4 in overtime, but a lot of Leafs fans will be rejoicing with the news that general manager Brad Treliving will no longer be employed by the organization.
But while the team is all but certainly set to miss the playoffs for the first time since 2016, it's possible to view this move as the potential herald of a new age. Sure, Maple Leafs Sports and Entertainment will still be running the show, but is the front office finally waking up to the reality that Leafs fans have awoken to since 2020?
There was an image of a cover page of The Hockey News that I saw in a social media reel quite recently. It read "PLAN THE PARADE. Toronto will win the Stanley Cup. It's only a matter of when. And how many."
Spoiler alert: to this point, they've won no Stanley Cups.
But they did win several honors since 2018, including two straight playoff eliminations to the Boston Bruins, a loss to a 42-year old Zamboni driver (WHO WORKS FOR THEM!), the wrath of John Tortorella and the bubble, a blown 3-1 series lead against the Montreal Canadiens, "We Want Florida", and two 6-1 blowouts on home ice against the same Panthers team that deflated the hype around the Leafs ending their series win drought and now sent Mitch Marner to the Sin City.
I'm not going to comment on how Marner's new team is doing; he'd actually be leading the Leafs in points AND assists if he was still in Toronto.
Dare I continue?
The point I'm trying to make is that it seems that maybe someone in the front office has woken up to the team's struggles and the fact that things might actually get worse.
After all, Auston Matthews is eligible for an extension in the summer of 2027, and it's all but certain that his contract status will be a major storyline for the next two seasons. Other cornerstones like goaltender Joseph Woll will also be eligible for an extension in a year's time, while Matias Macelli's RFA status isn't exactly going anywhere. And despite being on pace for an improvement in the assist category, John Tavares is 35 years old and on a contract that will take him very close to his 40's.
So if Toronto is going to win a Stanley Cup, next year might very well be do-or-die.
But most importantly, who's going to step up to the plate?
The big name floating around hockey media just hours after the Leafs announced Treliving's departure? Soon-to-be-former St Louis Blues' general manager Doug Armstrong.
Throughout his career, Armstrong has won two Stanley Cups, the first as an assistant general manager with the Dallas Stars and the second as general manager of the St Louis Blues. It's also worth noting that he worked with current Leafs head coach Craig Berube during that 2019 run with St Louis.
He also served as the general manager for several iterations of Canada's senior men's hockey team. His biggest achievements in the role include two Olympic gold medals (2010 and 2014) and two World Championship titles (2007 and 2016).
If the Leafs were to get Armstrong out of his deal with the Blues, he would easily be the most talented and experienced individual to hold the role in over a decade. And his proven ability to construct championship-winning rosters could very well help to put together a roster that will finally get over the playoff hump and challenge for their first Stanley Cup in almost sixty years.
Could a coaching change be on the horizon?
While Berube has worked with Armstrong before in St Louis, it's not a guarantee the two would work together once again.
The coaching market may not have the largest amount of big-name options, but there are some out there. Peter DeBoer is still without a job even a year after being fired by the Stars, and he's more than capable of getting a roster to the Conference Finals. He's also undefeated in Game 7's, an area that the Leafs more than certainly need to rectify.
Bruce Cassidy will also be joining the likes of DeBoer on the unemployment list, having only recently been fired by the Vegas Golden Knights. Cassidy was the coach who led the Golden Knights to their first Stanley Cup victory in 2023, and he also helped guide the Bruins to a Cup Final appearance in 2019. Berube does have a Stanley Cup of his own, but Cassidy does have the edge when it comes to Stanley Cup Final appearances and playoff wins; his 62 playoff wins are almost double Berube's 34 postseason victories.
If the Leafs do end up moving on from Berube, there's a very good chance they'll opt to go down the experience path once again. Despite being a ways away from the postseason this year, Berube pushed this Leafs core to an Atlantic Division title and two games further than their 2023 counterparts (though that's not much of an achievement). Another experience-based hire could very well be what this team needs to take the next step.
But no matter which way one puts it, this is set to be the Leafs' biggest offseason in over 10 years. More changes might very well be made to the front office and the roster during the summer, but the Leafs absolutely have to nail their general manager hiring.
Only then can the Leafs start to think about moving past the years of playoff shortcomings that came under past iterations of the team.