The Edmonton Oilers are set to begin the 2026-27 NHL season on Tuesday, Sept. 29, against the rival Vancouver Canucks; they’ll play a home and home series starting in Alberta and concluding on Thursday in Vancouver.
For the Oilers, it begins a two-year window that superstar captain Connor McDavid is under contract; he signed a short-term extension last year during the final year of his previous deal, and he took a considerable discount at just $12.5 million per season.
Considering what some players have signed for this offseason, McDavid could easily be in line to sign the NHL’s richest deal upon his next contract.
But whether or not that next contract will be signed in Edmonton remains to be seen, and in the eyes of one notable NHL Insider, that won’t happen if they’re not Stanley Cup winners in either of the next two seasons.
NHL Insider Believes Connor McDavid Will Not Re-Sign With The Edmonton Oilers
Former NHL forward Jeff O’Neill, who is currently an analyst with TSN, believes that the chances of McDavid agreeing to another extension with the Oilers are “zero” if they don’t win the Stanley Cup in the next two seasons.
“I think it’s zero. He told them: I got 2 years here, and if we don’t win a Cup, I’m gonna do it somewhere else. […] When your assistant captain says, look around here, we’ve got 2 years to make this thing happen… I think that means something,” O’Neill said.
McDavid, whom the Oilers selected with the first overall pick in the 2015 NHL Draft, has captained the club to two straight appearances in the Stanley Cup Final; they lost both occasions in 2024 and 2025 to the Florida Panthers.
McDavid’s heartbroken reaction to losing a gut-wrenching Game 7 to Florida in 2024 made the rounds on social media for weeks, showing just how much the Ontario native cares about getting the chance to win hockey’s ultimate prize.
O’Neill isn’t the only one who believes that McDavid could choose to look for greener pastures when his current deal expires if Edmonton doesn’t get the job done by then.
Connor McDavid Said The Oilers Were Flat Last Season
Following their disappointing elimination in the opening round of the Stanley Cup Playoffs earlier this spring, McDavid echoed the sentiments of his teammate Leon Draisaitl that the club took a step backward in 2025-26.
“Yeah I feel the same way,” said McDavid. “It’s only a couple days ago I made those comments and I obviously feel the same as I did a couple days ago and agree with Leon. The organization has a whole has taken a step back and that starts with me, starts with Leon. We can all be better and we all need to be better.”
“Maybe we lost a little bit of that fire that we had the last two years,” said Draisaitl. “Because it’s been a lot of hockey, it’s been a long season. I don’t know if taking it for granted is what I would say but I do think that there’s many parts that just somehow we took a little step back.”
NHL Insider Sends Clear Message on Connor McDavid’s Oilers Future