The Edmonton Oilers are following the Maple Leafs’ restrictive salary cap blueprint. But there is one key difference

recently added Stan Bowman, general manager of the Edmonton Oilers, is currently facing one of the most depressing aspects of constructing an NHL team: roster costs increase with experience level.

This implies that any season that ends without a Stanley Cup victory—the Oilers nearly achieved this feat in June—could have been your greatest opportunity to do so.

Certainly that’s the least flattering implication of the contract extension for Leon Draisaitl announced this week. For all the talk about the deal being a signal of Connor McDavid’s long-term acquiescence to life in North America’s northernmost metropolis, given the well-documented friendship between the two stars, Draisaitl’s eight-year deal valued at $112 million (U.S.) means his cap hit of $14 million will supplant Toronto captain Auston Matthews as the NHL’s largest next season.

Considering Edmonton’s top defenceman Evan Bouchard is a restricted free agent also in need of a contract extension — and that McDavid will be eligible for another league-topping contract extension next summer — it’s an understatement to say the math only gets trickier from here.

In other words: Hello, Edmonton. Welcome to life as the Toronto Maple Leafs.

One of the easiest explanations for why Leafland’s current era has been such an unfailing disappointment, of course, is a top-heavy salary-cap structure that makes it difficult to credibly round out a roster. This coming season, for instance, Toronto’s four highest-paid players figure to earn an estimated 53 per cent of the salary cap. That’s up from a slightly less crippling 48 per cent last season, when the Leafs were typically short on depth.

For now, at least, the Oilers aren’t the Leafs. This season, the last year that Draisaitl will command of a bargain cap hit of $8.5 million, the Oilers’ top four highest earners will take up a comparatively modest 41 per cent of the salary cap. And while the Leafs’ famed Core Four are all forwards, at least Edmonton’s top four earners includes two forwards, McDavid and Draisaitl, and two defencemen, Darnell Nurse and Mattias Ekholm. Nurse’s $9.25-million hit is already the obvious albatross with no easy outlet, to be sure. But even bigger problems are coming.

This is where it gets difficult for executives. NHL orthodoxy gives a team in this position precisely two options: Pay the freight or get even worse. Never mind that paying the freight means that building a winner gets even more difficult.

The good thing for Bowman is this: His top-paid guys aren’t yet Stanley Cup champions, sure. But they have a history of delivering in games that matter.

“As great as they’ve been in the regular season, they’ve been able to step it up even more (in the playoffs),” Bowman said of McDavid and Draisaitl, speaking on Toronto’s TSN 1050 Wednesday. “Which is really hard to do.”

He can say that again. As good as McDavid and Draisaitl have been in the regular season — they rank first and third in points since they entered the league — it’s in the playoffs where they have separated themselves from the bulk of their contemporaries. McDavid’s career rate of 1.58 post-season points per game ranks third in league history behind only Wayne Gretzky and Mario Lemieux. Draisaitl’s 1.46 post-season points per game ranks fifth all-time.

The Leafs’ best guys haven’t stepped it up in the same way. Mitch Marner, the top current Leaf in career post-season points per game, ranks 51st on the all-time list at 0.88. Matthews is just behind him at 0.87. William Nylander comes in at a career rate of 0.80 points per game. Those are respectable numbers. As Bowman was saying Wednesday: It’s hard to score in the playoffs, when opponent scouting is on high alert. But the standard is the standard, set by Edmonton’s best. And the salary cap means to whom much is given, much is expected.

And measured against all that, Nylander has produced at about half McDavid’s rate in the playoffs. Speaking of grim realities: Nylander is about to step into a new deal paying him $11.5 million a season — just $1 million less than McDavid’s current cap hit.

Which goes to show you: NHL players don’t get paid in the playoffs. But teams are defined by who they pay.

Nobody’s pretending it’s easy. But it’s certainly easier if your franchise’s chosen big-money few return the favour when the games get big.

“Ultimately what it comes down to often times, is who can elevate their game in those pressure moments?” Bowman told TSN 1050. “I think that’s what separates great players from exceptional players.”

The separator is the Oilers have won seven playoff series with McDavid and Draisaitl as their best players. The Maple Leafs have won one with Matthews and Marner as their lead dogs.

Maybe there’s something to be said for losing before you win, for learning from failure en route to glory. But the sheer economics tell you there’s a lot more to recommend winning young. Bowman was GM in Chicago from 2009 until 2021, so he knows that story well. The Blackhawks won three Cups before stars Jonathan Toews and Patrick Kane turned 28 — around the time Toews and Kane began commanding top-of-the-league cap hits. They haven’t won a single playoff series since.

As teams get older, winning gets harder. Welcome to life as the Leafs.