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31 Oilers Questions: Is winning a Stanley Cup the only way McDavid will re-sign?
Photo credit: © Sergei Belski-Imagn Images
By Zach Laing
Aug 14, 2026, 17:30 EDTUpdated: Aug 14, 2026, 17:45 EDT
Connor McDavid could’ve asked for any dollar amount last summer as he entered the final year of an eight-year contract.
The Edmonton Oilers front office would’ve signed a blank cheque, and they would’ve done so merrily. After all, the fact that the best player in the world would want to extend with your organization is something to be proud of.
But McDavid didn’t do that. He signed a two-year extension at the same $12.5-million cap hit he carried over the length of what was once the benchmark contract in the National Hockey League. Players now, of course, have blown by that mark — seven players will carry larger cap hits than he next season.
The message McDavid sent was clear: I want to win a Stanley Cup in Edmonton, and I want to make it easier to build a team around me.
All of the noise last summer was loud about McDavid’s contract status, providing more than enough conversations about what his next deal would look like, and we’re not far away from reaching that point again. By the time next summer rolls around, McDavid will be eligible to sign an extension with the Oilers, and time is running out to ensure he wants to do that.
Whatever transpires, the Oilers need to do whatever they can to ensure he re-signs next summer, or at the latest, before he has a chance of hitting the open market. It begs the question of if the only way he would stay is by winning a Stanley Cup.
The argument for McDavid staying with a Stanley Cup win feels fairly straightforward, no? McDavid has said time, and time, and time, and time again (I could keep going, too) that he wants to win a Stanley Cup. Hoisting Lord Stanley’s Mug would surely keep him in Edmonton for the long-term.
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The argument for McDavid staying without a Stanley Cup win
This is where things begin to get complicated. It’s been generally understood that as long as the Oilers are remaining competitive, that McDavid will continue to stay with the team. Seasons like last won’t cut it, and if the next two playoff runs are short, it’s hard to see him wanting to stay. Who could blame him?
After taking a significant pay cut for the Oilers to win with him in Edmonton, Stan Bowman and the front office’s inability to keep this team a perennial contender could drive others out of town, too.
But further deep runs could be enough to keep him in Edmonton, too. That means the Oilers are continue to spend assets to get better today, whether that be by way of using up cap space, or trading out picks and prospects to find NHL players today.
Mike Babcock’s hiring will play a factor, too. One has to wonder, given how much McDavid and the other Oilers leaders backed his hiring, if there’s a sense of loyalty to sticking by the bench boss. It’s unknown how long Babcock’s contract is for, but that loyalty could be there if it’s a multi-year contract of three years or longer.
I’m of a personal belief that Cup or bust, McDavid will be an Oiler for life. Earlier this year he spoke about being asked if his legacy matters to him, and his answer was clear:
“I’m 11 years into my career. Of course I think about my legacy. I want to be remembered as a winner. But not just anywhere. Here. To be in this city during a Cup run, to feel that buzz … it just wouldn’t be the same somewhere else.”
Whether it’s just one Stanley Cup or not, McDavid has a chance to do something that none of the other superstars who donned Oilers jerseys in the glory days did: play out his whole career in Edmonton.
Zach Laing is Oilersnation’s managing editor and The Nation Network’s news director. He can be followed on X at @zjlaing, or reached by email at zach.laing@bettercollective.com.
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Edmonton OilersTeam Cap Summary
Cap Summary
2026-27
2027-28
Projected Cap Hit
$99,274,166
$87,350,000
Projected Cap Space
$4,725,834
$26,150,000
Current Cap Space
$4,725,834
$26,150,000
Active Players
23/23
15/23
Draft Picks
Round
'26
'27
1
0
0
2
1
1
3
1
0