How The Montreal Canadiens Are Avoiding a Divisional Rival's Biggest Mistake

The Montreal Canadiens are at the end of the tunnel that has been this multi-year rebuild. Since going to the Stanley Cup Final in 2021, the Habs have been bad. Really bad. They were the worst team in 2021-22, and got the first overall pick, and have picked 5th overall in the last two seasons, which has really stocked the cupboards.

So the end is in sight, but not quite there yet. Montreal's best prospects, Ivan Demidov, Juraj Slafkovsky, Lane Hutson are still years away from their prime, and the team will more than likely still be bad this year, especially with big offseason acquisition Patrik Laine missing a good chunk of the year. Although, they might be able to weather that.

With one more year of high, and more importantly, good drafting, the Montreal Canadiens should be well set up for Stanley Cup contention for years and years to come.

But we don't want just Stanley Cup contention, we want Cups. And there is a team that is stuck in Stanley Cup '''contention''' but without winning anything in this player generation: the Toronto Maple Leafs.

The poor, poor, Maple Laffs. At this time, the Montreal Canadiens' biggest Canadian rivals have been mired in such a slump lately, and frankly I feel sorry for them. Now, the Boston Bruins, the Habs' other biggest rival? They are a team to hate, and it looks like they sold their souls for decades of success with the implosion of their top tier goalie tandem.

But the Maple Leafs? They are a team to pity. They haven't won the Stanley Cup since 1967, they haven't reached the Conference Final since 2002. There's only so much abuse a single team can take before you feel sorry.

For a long time, the Leafs were plagued with terrible teams, and terrible drafting that kept the team near the bottom of the league, but lately, their regular season luck has fully changed.

The Leafs have a plethora of high-end homegrown talent. The Leafs drafted and developed four of their biggest names themselves, Morgan Reilly, William Nylander, Mitch Marner and Auston Matthews. All four of those players have at one time or another been towards the top of the league in their respective areas.

And yet, the Toronto Maple Leafs in the Matthews-Marner-Nylander-Reilly era have made the second round of the playoffs once, and never made it to the third.

Why? Because the Toronto Maple Leafs sold their soul.

Everyone remembers this photo right? It was pretty ubiquitous when John Tavares left the New York Islanders in free agency for the Toronto Maple Leafs, his childhood team, in 2018, for a massive sum.

It was a great story, and Tavares would become captain of the team for years, but even at the time pundits were questioning the signing. It was an addition to what was already a strength for the team, and paying a premium for it as well.

And then, because Tavares' contract was huge, and Nylander, Matthews and Marner were even better, those three had to be paid accordingly, and they were. Reilly didn't get as big of a payday, but he still made a pretty penny.

Tavares, Nylander, Matthews and Marner make around $46.65 million this year. The cap ceiling is $88 million. That leaves around $41 million for the rest of the team. If you notice, that is less than those four players combined.

If you take away Tavares' $11 million cap hit for the past 7 years, the team is still rather top-heavy, but $11 million is a lot to play around with, especially for a team that has a lot of holes, namely on the defence, goaltending and depth forwards.

The Leafs had a revolving door of goalies at this time. Frederick Andersen was a regular-season stud but struggled in the playoffs. Matt Murray never got off the ground. Jack Campbell grew into a genuine starter before he priced his way out of Toronto and fell apart in Edmonton. Ilya Samsonov never fully solidified himself as a quality starter and Joseph Woll has potential but still has to develop.

The fact is that the Maple Leafs never drafted a great goalie which, fair play, is as much a shot-in-the-dark as there is in the NHL draft, but they also could never afford to trade or sign a high-quality goalie, a player that the team has desperately needed.

It's a similar story on defence. Reilly is the lone stalwart, but the team has struggled to fill his partner spot and pairs below him with quality first and second-pairing NHL players. Toronto's depth forwards are populated with gritty, grinding, defensive forwards, who struggle to score, and then cannot score in the playoffs.

So, what's the lesson to be learned from the Toronto Maple Leafs?

When faced with the choice between strengthening a weakness, or doubling down on a strength, go for strengthening a weakness. If the Leafs never signed Tavares and instead signed a great starting goalie, and a great defender, we might not be talking about what could have been, and what was.

The good thing is, the Montreal Canadiens seem to already be looking at depleting an area of strength to address an area of weakness.

Think of the current Canadiens team. What is their biggest strength? The young defence, without question. With prospects like Logan Mailloux, Lane Hutson and David Reinbacher along with young established NHL players Kaiden Guhle, Jordan Harris and Arber Xhekaj, along with many more not mentioned (Struble, Baron etc.). The back end is looking a bit crowded.

But goal-scoring and veteran forwards? That is a little thinner. Brendan Gallagher is great, but he isn't even close to the player he once was. Josh Anderson is fast and big, and that's about it. Christian Dvorak is there. So, the Canadiens took from one of their strengths and added to their weakness.

The Canadiens traded for veteran goal-scorer Patrik Laine for young defender Jordan Harris. If the Montreal Canadiens went with the Toronto Maple Leafs school of team-building, they would just pay all their existing defenders a lot of money, and throw a bunch of money at someone like Moritz Seider or something.

The fact that the Canadiens are putting these roster moves together, even in a relatively small move like Laine for Harris, it shows that the Canadiens' brass and team are thinking the right way and making the right moves. It puts them one step above the Toronto Maple Leafs, and that brings great hope for the future.