Amongst a (lack of a) flurry of moves across the NHL on Trade Deadline Friday, the Leafs got in on the action. Instead of short-sighted “buy now” moves, however, the front office finally accepted that they need to shift their focus to the future. A decade too late, perhaps.

The back-to-back (in New Jersey to play the Devils Wednesday and 20 km away Thursday to play the Rangers) saw Bobby McMann, Scott Laughton, and Oliver Ekman-Larsson as healthy scratches. For those just tuning in, these players were held out for potential trades out of Toronto.

Admittedly, selling now is better than another first-round playoff exit. The Leafs are also the only NHL team to not win a gam since the return from the Olympic break.

But this depth-acquiring and future-building should have come quite literally a decade ago. There’s a little trip down memory lane. The team-building should not have stopped with the drafting of Auston Matthews.

It’s been a decade of tinkering with the same roster. It clearly hasn’t worked. Why not embrace a more aggressive rebuild? If not now, when? The summer? If not then, when? The summer three summers from now?

On Thursday afternoon, hours before playing the New York Rangers at Madison Square Garden, Toronto traded Nicolas Roy to the Colorado Avalanche for two future picks.

Roy was acquired in July 2025 when the Leafs executed a sign-and-trade, sending Mitch Marner to the Vegas Golden Knights. Safe to say that this season has shown moments where the Leafs have sorely missed the hometown guy’s playmaking, especially as the power play quarterback alongside Auston Matthews.

On Friday, Toronto made only two more moves. These trickled in after the 3pm EST deadline as there was no doubt a lineup of deals that the NHL office had to confirm around that time.

Bobby McMann went to the Seattle Kraken for two more draft picks. Undrafted, McMann played 200 games for Toronto (91 points) and had 19 goals before the deadline. As well, Toronto sent Scott Laughton to the Los Angeles Kings for two more draft picks. What’s annoying is the leafs could not recoup a first-rounder back for Laughton.

The moves that needed to happen did indeed end up going through, thankfully. That being said, this trade deadline was, from where I sit as a frustrated and fed-up fan, all about damage control. And it was nowhere near enough.

The year before the Leafs drafted Auston Matthews, another generational player went #1 overall to the Edmonton Oilers. Connor McDavid. You may have heard his name thrown around with the all-time greats. Rightfully so.

Connor McDavid missed the playoffs in three out of his first four seasons. The exception was a second-round exit in his second pro season (2016-17).

He and the Oilers have come up short in two straight Stanley Cup Finals, but they’ve made it there.

Another example is Nathan MacKinnon. Like McDavid, “Makinen” (as Ricky from Trailer Park Boys calls him), missed the playoffs in three of his first four seasons. MacKinnon’s rookie year, the Avalanche lost in the first round to the Minnesota Wild in seven games. They then lost again in the first round to the Nashville Predators in six games. The following year, a second-round loss in seven games to the San Jose Sharks.

Watching the Olympics last month, and especially the Men’s Hockey gold medal game, anyone could tell that MacKinnon seems to take losses personally.

He’s now a Stanley Cup Champion, having finally broken through in the 2022 playoffs. It took him a decade in the NHL to finally hoist the Cup.

Despite losing both series to the Florida Panthers, Connor McDavid and the Edmonton Oilers have made two straight Cup finals and it wouldn't be the most unrealistic thing if they ran through the western conference this spring. But MacKinnon and the deep, loaded up Avalanche might have something to say about that.

Maybe there’s a correlation there. Maybe I’m grasping at straws. But maybe Auston Matthews (and the Leafs) could have benefitted from a similar lack of playoff presence through the early years of his NHL career.

Short-term pain for long-term gain, or something like that.

Barring a massive turnaround, the spring of 2026 will see no NHL games in Toronto. And that also feels like it’s about a decade too late.