NHL Shocker: Winnipeg Jets and Pittsburgh Penguins Poised for Game-Changing Trade Moves?

As the dust settles on the upcoming hockey season, one question keeps echoing louder than the roaring crowd in Winnipeg’s arena—when exactly will Kyle Connor put pen to paper with the Jets? Murat Ates from The Athletic, a sharp eye on the pulse of the team, hints that while Johnathan Toews could solidify the crucial 2C spot if he keeps fit, the real headache for the Jets is locking down Connor’s future. This isn’t just any contract renewal; it’s poised to set a new benchmark as the heftiest payday in Jets history. With the salary cap rising steadily over the next few years, parallels are being drawn to the big-ticket deals inked by stars like Mikko Rantanen and Mitch Marner, whose contracts sport an average annual value north of $12 million. But the calculus won’t be just about raw numbers—it’s a delicate dance tied closely to a growing roster of 2026 free agents, including LA’s Adrian Kempe, who’s slated for a substantial payday himself. Connor’s contract saga is shaping into a complex chess game where timing and market signals will be everything, and waiting on who breaks first might make or break the deal. Curious about how this all unfolds? LEARN MORE

When Does Kyle Connor Sign with the Winnipeg Jets

Murat Ates of The Athletic: Ates writes in his column about Johnathan Toews and what he can bring to the team. If Toews stays healthy, he can be a 2C, and the Winnipeg Jets don’t have to worry about that problem. The bigger issue for the Jets is the contract extension for Kyle Connor.

When it comes to Connor and his contract extension, he will be the highest-paid player in Winnipeg Jets history. With the salary cap going up over the next several years, the Mikko Rantanen and Mitch Marner contract extensions that carry an AAV of $12 million a season could be the starting point. However, it would be more of a percentage of the cap than what Mark Scheifele and Connor Hellebuyck are getting.

This process will be complicated by the presence of other notable free agents in the 2026 class. There is a guy in Los Angeles named Adrian Kempe who will get over $10 million, and Kyle Connor’s numbers are better than his. So the market will be set by whoever signs first.

NHL Rumors: No Issues Between Kyle Connor and the Winnipeg Jets Over Contract

Was There a Purpose to Sidney Crosby’s Agent Talking About the Future

Josh Yohe of The Athletic: Yohe held his annual mailbag and was asked about why Sidney Crosby’s agent, Pat Brisson, mentioned to Pierre LeBrun of The Athletic about the potential his client could be on the move. This was more about ensuring that his wingers, Bryan Rust and Rickard Rakell, don’t get traded.

As Yohe mentioned, these comments were calculated, and his client may not be happy with the fact that his agent made the statements he did, but this was about ensuring the captain’s satisfaction and ensuring the Penguins have a successful season. Although playoffs might be out of the question, if Pittsburgh performs better than expected, maybe they won’t sell off the pieces everyone thinks they will.

And as Yohe said in another post in response to a question about Sidney Crosby and Evgeni Malkin being traded, he doesn’t think that will happen. Several factors could lead to both parties being traded, including both parties informing management that they want out.

NHL Rumors: Free Agent Rumblings, and the Pittsburgh Penguins

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