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If you are a Connor McDavid fan, you have only 1 thought on your mind: when will the Oilers captain lift the Stanley Cup? Many will agree that the 28-year-old more than deserves his first Stanley Cup ring after years of top level performances. NHL legend Joe Nieuwendyk certainly thinks so. It doesn’t matter that he is a Calgary Flames Hall of Famer who’s supposed to hate the Oilers. He is just rooting for the Oilers captain, that’s it. “I hope Connor McDavid wins a Stanley Cup, and I promise Flames fans that when he does, I’ll go back to hating the Oilers again.”

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Hey, nobody wants to see that happen more than an Oilers fan. Although, since the events of the 2025 Stanley Cup Final, there is one lingering doubt that has only gotten more and more traction as the summer has progressed. Even if McDavid wins the Stanley Cup, will it at all be in an Oilers shirt?

Because to do that, the Oilers captain has to stay at his current team, where he is in his final year of his contract. And speculations are just running wild, especially since he is yet to put pen to paper. But the Canadian center recently addressed the contract situation, which vaguely suggested he may be staying in Edmonton. And maybe that’s why Paul Bissonette is changing his stance? Or is he?

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It all started when former NHL defenseman Ryan Whitney confronted his co-host on the latest Spittin’ Chiclets episode, which was uploaded to YouTube on September 2nd. “Do you guys want to maybe say, ‘I’m sorry’ yet?” went Whitney. “I don’t know if you saw Connor McDavid at Canada’s Olympic orientation camp. Like, he will be signing with Edmonton, Biz. You, you’ve been saying forever he won’t.”

Technically, McDavid hasn’t confirmed anything yet. But he did give a positive outlook as far as the Oilers are concerned. And that was enough for Whitney to call out Bissonette, who was like, “No, no, no, no. That’s not true … I said that I think he’s going to sign a two-year extension.” Changing his stance now, is the TNT commentator? Bissonette continued, “And then he’s saying, “Bye-bye. I’ve done my time here.”

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He was pretty certain that McDavid wouldn’t win the Stanley Cup in Edmonton because the Oilers just wouldn’t be able to put a winning team around him. They still haven’t solved the goalie problem that cost them the 2025 final. The team is always changing, the problems are endless. In fact, back in October 2024, Paul Bissonette publicly called out the team in a tweet: “Can’t believe the Oilers wasted McJesus’ prime. Come home, Connor. It’s time to end the drought. #LeafsForever”.

The former Penguins defenseman has repeatedly wanted Connor McDavid to join the Leafs. But he definitely thinks McDavid won’t stay for more than 3 years. Although Whitney believes McDavid will sign a 3-year extension, and win the Stanley Cup there. Why? Because McDavid said so.

As of now, both the Spittin’ Chiclets hosts agree on the fact that Connor McDavid will renew. And even veteran reporters think so.

Connor McDavid finally broke his silence

It was back on June 20 that the 2024 Conn Smythe Trophy winner had asked for some time to make his contract decision. And then, it was radio silence for more than 2 months. Until August 27, when he spoke about the contract situation. “I have every intention to win in Edmonton. That’s my only focus … maybe next to winning a gold medal with Canada.”

This is what got Whitney and probably every Oilers fan excited. But nothing’s concrete yet. As McDavid, also added, “I’d say all options are on the table, really. We’re going through it. I don’t have a preference either way.”

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The McDavid camp hasn’t approached the Oilers management for talks, and Oilers GM Bob Bowman had clarified that the negotiation talks will be driven by the player: “Timing-wise, Connor is going to drive that process.”

So, is there a real positive for the Oilers in this situation? Well, there’s consolation that even veteran reporters with decades of experience think McDavid is going to extend the contract sooner rather than later. It’s just how big the contract is going to be, with NHL-record figures being thrown into the discussions.

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