While the Montreal Canadiens continue to have success, their longtime rivals, the Toronto Maple Leafs, have finally acknowledged that their Stanley Cup window has closed.
With that in mind, let’s take a look at some of the lessons Canadiens should remember as the Maple Leafs attempt to identify what went wrong.
1 – It’s a long way to the top if you wanna rock and roll
When it comes to building a roster competitive for the Stanley Cup, there is no foolproof recipe, and the best laid plans of mice and men often go awry.
Take the Washington Capitals, for example.
Even with the best goalscorer in NHL history in the lineup, it took them two years to qualify for the playoffs. And once Alex Ovechkin got his first taste of springtime hockey, it took 11 years for him and the Capitals to finally capture the Stanley Cup.
It’s been 12 years of disappointment, a heavy price to pay for any fan base.
In fact, many of the best teams in NHL history have failed miserably in their respective playoff contests. The Boston Bruins scored the most points in league history in 2022–23 with 135, and yet, they lost to the Florida Panthers in the first round. The Tampa Bay Lightning scored 128 points in 2018–19, the third-most in NHL history. They were eliminated in the first round by the Columbus Blue Jackets in four consecutive games.
The Maple Leafs were never able to get beyond the second round, failing to win two series for nine years in a row, which ultimately led them to remove talented players from the mix in exchange for more conflict, a recipe that slowly but surely eluded them from the ultimate prize.
The lesson in this case is that it’s not always easy to convince passionate fans like Montreal and Toronto to show a little more patience.
Simply put, winning the Stanley Cup is incredibly difficult, and some of the greatest greats in league history have failed to lift hockey’s Holy Grail.
2 – Property Management
While there is certainly some logic involved in trading future assets for NHL-ready players, a trend that was popularized by the Lightning, there must be some semblance of asset management there.
The Leafs have traded many of their first-round picks, with little long-term value in returns. Spending a first-round pick on a defensive defenseman like Brandon Carlo, while only convincing the Bruins to provide top-5 pick protection, is the epitome of a high-risk, low-return type of deal.
Why is Boston’s Brandon Carlo draft pick only protected in the top five?
Brad Treliving: “Because that’s what we had to do to get the deal done last year.”
How hard did you work for top-10?
“We pushed.”
– Luke Fox (@lukefoxjukebox) 6 March 2026
Another good example of a wasted asset was the acquisition of Scott Laughton. The Leafs once again used a first-round pick to complete the deal, and while Laughton provided more energy to the team than most of his teammates, he was ultimately dealt to the Los Angeles Kings at the NHL trade deadline in exchange for a conditional third-round pick.
It’s easy to criticize with the power of hindsight, although I would argue that both deals were easy to criticize even in a contemporary setting.
The Canadiens have already traded some of their picks in the first round, including the deal they got for Noah Dobson, however, they ensured that he will be with the team throughout his tenure, and he fits into the ideal age group of the rest of the main players.
Adding players can be great, and first-round picks are fine as long as the deals stick to the vision set by management.
3 – Make a plan, stick to it
Speaking of vision, it’s quite clear that the Maple Leafs struggled to establish a long-term vision with their talented group of players. Having a blind spot big enough for two divisional rivals should be considered a hockey sin.
You could even argue that this is still an issue, based on Keith Pelley’s recent press conference.
Thoughts on the Pele presser:
1) They still have no vision. No firm was hired, no hierarchy was set. That doesn’t mean they won’t get it right, but they are just promoting it.
2) Pelé told prospective GMs he didn’t want to hear about scorched-earth rebuilding.
– Brian Hayes (@HayesTSN) 31 March 2026
Luckily for the Canadians, sticking to the plan is the name of the game in Montreal, but the pressure will eventually mount.
At that point, the temptation to stray from the plan will emerge, and it will be up to Kent Hughes and company to stay true to their original vision.
4 – Scoring is fun, defending is important
The Canadiens, like the Leafs, love to score goals, but it’s fair to say that defense usually takes a backseat when it comes to their on-ice tactics.
Having a good goaltender may help hide the problem, but it doesn’t address the root of the problem.
Former Calgary Flames analyst Kent Wilson said it best.
“Stopping shots is like killing rats. It’s better not to do it, but if you’re doing it all the time it tells you that you have bigger problems.”
The Canadiens block as many shots as they allow too many shots, a situation that risks being exposed in the seven-game series.
Aside from a first line of Juraj Slafkowski, Nick Suzuki and Cole Caufield, most Canadiens lines have difficulty outplaying their opponents. As far as defensemen, with the exception of Lane Hutson and Adam Engstrom, they also tend to lag.
The Habs are one of the most entertaining teams in the league, and they have a penchant for staging comebacks late in games, but that’s symptomatic of a larger issue that has plagued them for years.
As the saying goes, defense wins championships.
5 – Keep the pipeline flowing
The Leafs did a good job putting together a relatively strong lineup, however, it would be hard for you to argue that they bolstered their lineup with a steady stream of young, talented players.
Trading away first-round picks like Candy was part of the problem, and there were some highlights like Matthew Nease, but for the most part, the Leafs had to pay a high price to add mediocre players to the lineup.
Having prospects like Michael Hayes, Alexander Zarovsky and LJ Mooney up front, not to mention Bryce Pickford, Adam Engstrom and David Reinbacher on the blue line, should ease this concern somewhat, but it may not sustain the team for 10 or more years, especially if draft picks start to dry up.
A healthy balance between drafting and using draft picks to improve an NHL roster is always in order.
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