Edmonton Oilers forward Connor McDavid handles the puck against the Vancouver Canucks in the second period of their preseason game last week at Rogers Arena.Bob Frid/Reuters
The most impressive thing Kirill Kaprizov did over the summer wasn’t signing for US$17-million a year, the biggest pay packet in NHL history. The really amazing thing he did was turn down US$16-million a year.
Kaprizov is a very good player on an average team. He’s Mitch Marner without the Toronto hype machine.
If that guy is pushing 16 million bucks back across the table, the economics of hockey salaries needs a big rethink. The other shoe dropped on Monday, when Connor McDavid extended his deal with the Edmonton Oilers.
The Oilers want to marry the best player in the game. The best player in the game wants to date a while longer. McDavid agreed to sign a two-year, US$25-million extension.
This is good news for the Oilers but it isn’t great news. The club has been put on notice – be good, or else.
Once last season ended, McDavid immediately began transmitting soft signals of discontent.
“If I feel there’s a good window to win here over and over again, then signing is no problem,” he said.
At 28 years old, McDavid is right to feel a sense of urgency and he wants the Oilers to feel it too.Perry Nelson/Reuters
This was broadly taken as a threat, and an unreasonable one. The Oilers had just made two Stanley Cup finals. What else does the guy want? No team can win every year.
Via his decision on Monday, McDavid begs to differ. When a player of his stature begins to differ, others will get ideas.
This isn’t just one guy passing up some guaranteed money. It’s a reimagination of the relationship great players have with the teams they play for.
Had McDavid signed long-term, the Oilers could have relaxed. Nobody’s going to say that, but it is the effect of securing your most important employee. Now you’ve got the next eight, 10, years taken care of. You can Pittsburgh Penguins yourself into permanent mediocrity, knowing you have Sidney Crosby to sell tickets.
The Edmonton Oilers agreed to a two-year, US$25-million contract extension with captain Connor McDavid on Monday, ending months of speculation about his future
The Canadian Press
No team wants to do that. But now they can. Knowing that they can changes the organizational temperature from red-hot desperation to the warm fuzzies.
McDavid must sense that. Why else is he always going on about ‘if’ this happens in Edmonton and ‘maybe’ that?
He’s 28. Brad Marchand aside, players don’t get better in their 30s. McDavid is right to feel a sense of urgency. He wants the Oilers to feel it, too. He’s just made sure they will.
Now no one, from ownership down to the fourth line, has the luxury of slipping. No tactical retreats, no mini-rebuilds, no first-round letdowns. The bar is up here, higher than you can reach.
To be safe, the Oilers have to either win it all or come very close for the next three years.
If they do that, McDavid may deign to sign a long-term deal just as the salary cap jumps.
If they don’t, maybe the Florida Panthers are looking for some help.
What business leaders can learn from Connor McDavid
This is a reversal of common wisdom. For teams, you want your top end talent under contract for as long as possible. For players, you want to maximize your earning right now, when you can be certain you will get it. There’s a good business case to be made that it makes sense, for both sides.
Unless money and marketing stability are not your primary drivers. If winning is all you care about, short-term deals apply maximum pressure to performance.
Imagine if the Leafs could get McDavid, but only for one season. What would that Leafs team sound like? You think they’d roll into a preseason presser trying their usual dodge about specific expectations?
If McDavid was willing to come here time limited, Leafs GM Brad Treliving would be up on a table with his shirt off shouting, “THIS IS OUR YEAR. MARK IT DOWN.”
Truly great players in other sports have discovered the magic of this trick. LeBron James has spent most of his career going from short-term deal to short-term deal. Once the team he’s on starts to slip, James is gone. That’s why his teams always matter.
Tom Brady used the same pressure to keep the Patriots honest during his last few years there. As soon as he left, the team cratered. He’d been holding them together, not just through his play, but via force of will. He wanted them to win, so they had to.
Anyone with enough ability can do this. You just have to care more about winning than money. Not just saying that, which everyone does, but taking steps to show it’s true.

Teams want their top end talent under contract for as long as possible, but players want to maximize their earning right now.Steph Chambers/Getty Images
No one does that sort of steel in hockey. Everybody’s grabbing whatever they can, trying to squeeze a few more years out of whatever team they play for, regardless of where they’re headed. Kaprizov in Minnesota is a good example.
Maybe it’s Rick DiPietro’s fault. The once touted goalie signed a 15-year deal with Islanders, played seven of them and not very well. They’re still paying him more than a million bucks a year.
Who wouldn’t want free money? More importantly, what if you sign a two-year deal and get your foot run over in a Costco parking lot? Don’t think too hard. Take the money.
McDavid just changed that channel. Until now, he’s made about US$90-million in salary. I guess he figures that’s a decent cushion if it all ends tomorrow. It’s too bad more people don’t have his sense of proportion.
What he’s done is exchange money for influence. If he didn’t already, he definitely runs the Oilers now. His is the final desk every decision goes across, metaphorically. Nothing can happen without his consent. Otherwise, it’s curtains in a few years.
There’s no saying for sure what effect it will have on the team this year. Telling someone they have to win won’t make them win. But now, unlike most other teams in hockey, the Oilers know they have no permission to lose.

Short-term deals like McDavid's apply maximum pressure on teams to up their performance.Steph Chambers/Getty Images