Insider hints at the real reason McDavid has not signed.

Perhaps the biggest story in the National Hockey League right now is the fact that Connor McDavid, considered by most to be the best hockey player on the planet, has yet to sign a new deal and appears poised to head into the 2025-26 NHL regular season as a pending unrestricted free agent.

Everyone has been trying to figure out why things have ended up where they are now and this past week the NHL's top insider, Elliotte Friedman, did his best to shed some light on the situation based on what he's been hearing. Friedman's first comments on the topic were comments that I would be concerned about as an Oilers fan, with the insider admitting that this decision from McDavid has caught him off guard.

"I have to say, I admit, I am surprised at this," revealed Friedman on the 32 Thoughts podcast. "I thought we would get back to camp in Edmonton and we would find out that Connor McDavid was singing a short term deal with the Oilers."

Friedman believes that the hesitation to sign on McDavid's part come from a burning desire to win a Stanley Cup. The insider discussed just how much the last two Stanley Cup Finals, both losses for the Oilers, have impacted McDavid and have made him even more rabid when it comes to his ultimate goal of winning it all.

"I think that is purely what this is about," said Friedman. "The two loses have angered him and disappointed him and pained him so much that he will not allow himself to be put into a situation where he doesn't think he's capable of winning."

So what is the issue with the Oilers, a team that has made it to back to back Stanley Cup Finals? Well that may boil down, at least in part, to a fateful series of decisions that most feel made the Oilers a much weaker team last season.

"They lost [Philip] Broberg and they lost [Dylan] Holloway last year, players who could be cornerstones of the future for the Oilers, and that's left some holes that they are trying to fill," said Friedman.

When Friedman was pressed on whether or not he believed losing both Broberg and Holloway was impacting McDavid's current decision not to sign, he answered in the affirmative.

"It's impossible to believe it's not," said Friedman.

The Oilers were of course unable to match the offer sheets for Broberg and Holloway due in part to the catastrophic signing of veteran forward Jeff Skinner to a one year deal at an average annual value and cap hit of $3 million, a move that wasn't made by either Oilers general manager Stan Bowman or his predecessor Ken Holland. Instead that move was made by Oilers CEO Jeff Jackson, who was serving as interim GM during the transition between Holland and Bowman and who just so happens to be McDavid's former agent as well.

If that fateful series of decisions proves to be the end of the McDavid era in Edmonton, I don't think fans will be quick to forgive Jeff Jackson for what is already viewed as a highly controversial signing.