I’ve lost track of how many times it’s been suggested one way or another since 2015 that if the Edmonton Oilers didn’t get their act together and win something — notably the Stanley Cup — in a hurry, Connor McDavid will pack his bags and look elsewhere for a place to play.

It seems more of a punchline offered up between fans having a go at each other than an actual possibility – that’s the way I’ve taken it the last five years as the Oilers have morphed into a contending team. The Decade of Darkness is long over, just an ugly speck of futility in the rear-view mirror. As McDavid running mate Leon Draisaitl said when the Oilers bowed out in the second round this spring, it’s Stanley Cup or bust now.

The Oilers haven’t won anything, but they’re no joke. After back-to-back seasons of 109 and 104 points, why would McDavid, who is under contract through 2025-26, want to get out of town? Same for Draisaitl, signed through 2024-25. Where else can the NHL’s most dynamic duo play with a legit contender, given cap considerations? Where else is the grass greener?

With what Jeff Jackson, McDavid’s former agent and just-hired CEO of hockey operations with the Oilers, is saying and what in-the-know insider Frank Seravalli of DFO Rundown is hearing, I don’t think McDavid or Draisaitl are going anywhere. Seravalli pegged the chances that both of them will stick around “for some time” at 90 per cent.

Jackson’s arrival from the Wasserman agency in itself and what he said in an interview with Bob McCown this week, has me thinking more along the lines of 100 per cent – unless this team falls off the edge of the earth over the next couple of seasons. I don’t see that happening. Does anybody?

In hockey, like in every walk of life, relationships matter, and Jackson and McDavid go back a decade. Jackson talked about that when he was unveiled as CEO. He reiterated what that might mean in his conversation with McCown on Monday. That said, Jackson isn’t looking back, he’s looking ahead.

“I think that the Oilers are in a good spot,” Jackson told McCown. “It’s been a while he’s been there — eight years. There have been frustrations, but there’s also been continuous building of a team that can compete. The city of Edmonton has embraced him.

“We have amazing fans. Darryl Katz has done everything in his power, with the building and Ice District and everything in the downtown. Players are treated extremely well. It all will come down to us doing our job to surround (McDavid) and Leon and the rest of the core with the important parts that are going to help them get over the hump and compete.

“I’m confident that we’ll be able to do that. There’s no guarantee, but I have an understanding of his love of Edmonton and the team. I’m optimistic (he’ll re-sign).”

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