Leon Draisaitl and Connor McDavid of the Edmonton Oilers are an unstoppable tag team. Photo by BRUCE BENNETT /GETTY IMAGES

The NHL has had many great players, and in the past 15 seasons many of them made more than $10 million per year in salary.

But for all these great players have brought to their teams, no NHL team has yet won the Stanley Cup in the league’s salary cap era, 2005-24, with a player on its roster making more than $10 million per season.

My Cult of Hockey colleague Bruce McCurdy brought up this fact in our new podcast on Edmonton’s contract negotiations with Leon Draisaitl and, shortly, with Connor McDavid.

In recent years, Stanley Cup winning teams have had three players who made $10 million on the nose, Sergei Bobrovsky and Alexander Barkov in Florida and Jack Eichel in Vegas, but no team has gone all the way with a player making more than that.

Fourteen players made more than $10 million in cap hit in the NHL last season, with Auston Matthews leading the way at $13.25 million. Toronto had two other players in this group, John Tavares at $11 million and Mitch Marner at $10.9 million. But Toronto, once again, failed to win even one ground in the playoffs.

Drew Doughty of the Los Angeles Kings made $11 million last year, ninth most in the NHL. But his Kings were again bounced in the first round of the NHL playoffs.

Indeed, since Doughty’s deal jumped from $7 million to $11 million in the 2019-20 season, the Kings have failed to make the playoffs twice and been bounced in the first round three times.

The second great Kings player, Anze Kopitar, went from $6.8 million to $10 million a year in the 2015-16 season. In the four seasons before Kopitar’s raise kicked in, the Kings won two Stanley Cups. They did not win a round after Kopitar’s big salary boost happened.

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Last week I wrote of another such example, how the Chicago Blackhawks won three Cups in six years when star players Jonanthan Toews and Patrick Kane were on more modest deals, but despite Kane and Toews being near the top of their games, that team never won another first round in the playoffs after their new deals at $10.5 million per season each kicked in for the 2015-16 season.

What does this mean for Edmonton Oilers, Draisaitl and McDavid?

It’s evident that both Connor McDavid and Leon Draisaitl will sign new NHL deals for more than $10 million per season. But if they decide to both sign in Edmonton, what cap hit would be both reasonable for them but also give the Oilers a solid chance of having enough cap dollars to compete each year for the Stanley Cup?

To figure this out, I looked at each team that won the Stanley Cup in the cap-era to see what percentage of the ever-increasing salary cap their top two players have commanded.

That average turned out to be 23.1 per cent of the cap in a given year, with Scott Niedermayer and Chris Pronger of Anaheim taking up the greatest percentage, 29.5 per cent for the 2006-07 Anaheim Ducks, and Ryan 0’Reilly and Alex Pietrangelo taking up the lowest percentage, just 17.6 per cent for the 2018-19 St. Louis Blues.

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The Florida Panthers, with their two $10 million players. designated 24 per cent of the cap to Bobrovsky and Barkov, just about the average for NHL Cup-winners. By comparison, McDavid and Darnell Nurse, Edmonton’s two highest paid players, took up 26 per cent of Edmonton’s cap, which is higher than all but two Cup winners in the cap era.

Of course an NHL team could defy this trend. The Oilers could pay McDavid $15 million on his new deal and Draisaitl $14 million per year on his and still win the Stanley Cup in 2026-27, when I guesstimate the salary cap will be about $96 million. That would be 30.2 per cent of the cap going to McDavid and Draisaitl.

For McDavid and Draisaitl’s contracts to be in line with previous salaries earned by the top two highest paid players on Cup winners, McDavid would have to stick to his current salary of $12.5 million, with Draisaitl getting a boost to that same $12.5 million per season. That would have the two getting 26.3 per cent of the cap in 2025-26 and 25 per cent of the cap in 2026-27. Those are salaries at a level that the Oilers could work with to have a solid shot at the Stanley Cup.

But if McDavid and Draisaitl take home 30 per cent or 29 per cent or even 28 per cent of the Oilers’ total cap, it’s going to be difficult for Edmonton to go all the way, at least if the history of Cup winners is a guide, and if my singular focus on the salaries of the top two players is reasonable.

By the way, if McDavid and Draisaitl are looking for inspiration in this regard, they might want to talk to Sidney Crosby. When Crosby won his first Cup in Pittsburgh in 2009, he took home $8.7 million, 15.3 per cent of the cap of that time. But in his next long-term deal, Crosby stuck with that $8.7 million per year, turning his back on at least two or three million dollars a year if he’d done what most players would do in that situation.

Crosby has earned less in salary because of it. But his lower salary also helped Pittsburgh have the cap space to win two more Stanley Cups in 2016 and 2017.

Did he make the right call? You’d have to ask Crosby, though it may be impossible to quantify.

What’s the going rate for an NHL superstar? $13 or $14 million a year these days.

What’s the value of winning the Cup? Priceless.