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Best of Luck to Connor McDavid, But He's Taking a Huge Gamble That Could Just As Easily Blow Up In His Face

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Published: October 6, 2025 6:40 PM CST


As you may or may not know, Connor McDavid announced on his Instagram page (no credit to the journalists who claimed "sources" told them this) that he was re-signing with the Edmonton Oilers. It ended up being a 2-year extension for a well-below-market-value $12.5M AAV (average annual value).

Now, before I get into what I think about all of this, let me just say good for Connor McDavid for taking less money and giving the Oilers the cap space to sign the players necessary to put a winning team around him. He's obviously a team-first guy who just wants to win, nobody can question that now. We just saw Kaprizov sign for a record-breaking $17M AAV in Minnesota, not many players would be willing to do this (and they shouldn't, by the way. Get as much as you can get while you can get it).

However ... here's the real issue with what McDavid just did.

Connor McDavid now has no financial security beyond the next 3 years (the contract extension kicks in starting in 2026-2027, so he's under contract to Edmonton through the 2027-2028 season). If he suffers a serious injury, or, god-forbid, a career-ending injury, will Edmonton sack up and sign him to another contract extension as a severance pay of sorts to compensate him for his showing of good faith?

No, of course they won't. It's all business.

Connor is all in with Edmonton for 3 more years, win or lose. If he wins (and stays healthy), then fantastic -- mission accomplished. He can go on to sign a big money contract after that and get the money he deserves, be it in Edmonton or elsewhere.

But if he doesn't ... ?

Welp, then he just took a massive leap of faith for a group of billionaire sports owners that he may regret forever.

This is it for McDavid. One way or another, win or lose, he is more than likely gone from Edmonton once this contract is up. If he doesn't win? Of course he's gone, because he just sacrificed his money and his financial security for an organization that couldn't build a winner around him.

And if he does win? Well, frankly, he's probably still gone because he accomplished what he set out to do. He gave Edmonton a Stanley Cup and took a huge discount to do it.