Oct. 8: 8:37 a.m.: It will indeed be an eight-year, $96MM deal that pays Connor $41MM in signing bonuses over the life of the deal, according to Darren Dreger of TSN. The Jets have now announced the deal.

Oct. 8, 7:00 a.m.: Connor’s deal is expected to come in around the $12MM mark per season when done for a total value of $96MM, Friedman adds Wednesday. That would be the largest contract in franchise history. He’s also set to receive a full no-move clause and significant signing bonuses – something Winnipeg has never given out, not even in their landmark extensions for Connor Hellebuyck and Mark Scheifele two years ago.

Oct. 7: The Winnipeg Jets and star forward Kyle Connor have “made progress on a long-term extension,” Sportsnet’s Elliotte Friedman reported Tuesday night. Friedman added that both Connor’s camp and the Jets are working to secure an extension before the team’s season opener on Thursday. TSN’s Darren Dreger seconded Friedman’s report, saying both sides “are getting closer to a contract extension.” At the same time, The Athletic’s Pierre LeBrun added that he expects the upcoming contract extension to carry an eight-year term.

While a complete agreement on a deal has thus far proved elusive, the widespread expectation has long been that Connor would re-sign with the Jets, the only NHL franchise he has ever played for. Last month, owner Mark Chipman expressed confidence that the club would be able to re-sign its star winger, even going so far as to say that he expected that a deal would be completed “sooner rather than later.”

With today’s reports from some of the game’s most connected insiders, it appears Chipman was right. While the full terms of this expected contract extension are still unknown, signing Connor to such a deal would be a significant win for the Jets organization. Despite the Jets’ consistent on-ice success, Winnipeg has long faced an uphill battle in convincing players to commit to playing there.

The Jets are owned by a committed ownership group and are managed by a hockey operations department with a consistent track record of success. They can offer players the opportunity to play in front of a die-hard fan base that is the envy of most of the league. However, despite this, the Jets have had to contend with a perception among players that Winnipeg is not a premier free agent destination, a perception that has proved frustratingly persistent.

Back in 2019, 42% of NHL players polled by ESPN listed Winnipeg as the “road city [they] dread the most.” The team has not been a significant player at the highest levels of unrestricted free agency and is reportedly listed as a standard on players’ trade protection lists.

All of that is to say that the Jets face a different player acquisition landscape compared to other NHL teams. Teams such as the Florida Panthers and Dallas Stars have a favorable climate and tax situation, while others, like the New York Rangers or Los Angeles Kings, can market themselves as unique, destination cities to prospective players. Winnipeg has not been able to employ similar tactics to recruit players, instead building its Stanley Cup-contending team through a diligent draft-and-develop model combined with savvy work on the trade market.

Their model only works, though, if they are able to convince the players they draft and/or develop to remain in Winnipeg for the best years of their career, and in many recent cases, the Jets have had remarkable success doing so.

They’ve been able to re-sign franchise pillars such as Mark Scheifele and Connor Hellebuyck, as well key contributors such as Neal Pionk.

With today’s reports, it seems Connor’s name will soon be added to that list of key Jets players to commit to a long-term extension with the franchise. In re-signing Connor, they’ll manage to keep their most lethal scorer, and arguably their most important forward, on their roster for eight years after this one.

Since the Jets returned to Winnipeg, just two forwards have scored more points than Connor, and just one has scored more goals. His 0.95 career points-per-game ranks first in modern Jets franchise history. Connor also owns the two highest-scoring seasons in the modern history of the Jets, including his fantastic 2024-25 when he scored a franchise-record 97 points in 82 games.

He’s one of the game’s elite play-driving wingers, and he’s a threat to score whenever he steps on the ice. He’s a consistent playoff performer as well, and is coming off of the best postseason run of his career – he scored 17 points in 13 games during the Jets’ most recent playoff run.

All of that means Connor is unlikely to come cheap. It’s difficult to project long-term contracts at the top of the market at this point, as two of the most recent big signings were impacted by unique circumstances that are not applicable to other players and situations. Minnesota Wild superstar winger Kirill Kaprizov is in some ways comparable to Connor (both are play-driving true number-one wingers) but Kaprizov was widely seen as far more of a threat to test unrestricted free agency – making the Wild all the more willing to pay whatever it took to get his signature on an extension. That resulted in a $17MM AAV, something Connor, or any other player, for that matter, appears likely to match anytime soon.

And then there is the recent re-signing of Connor McDavid with the Edmonton Oilers. McDavid is the game’s unquestioned best player, but his extension carries a two-year term and just a $12.5MM AAV. Under normal circumstances, it’d be hard for Connor to argue that he deserves to make as much – let alone more – than McDavid, but again, it was a unique circumstance. It was widely reported that McDavid opted to be paid a notable amount less than his market value in order to maximize the Oilers’ ability to field an elite team to support him.

For what it’s worth, AFP Analytics projected Connor’s next contract to be worth just north of $12MM annually, and that would seem to be an appropriate price for Connor given his abilities, the market environment, and the rising salary cap. But at this stage, the only reports are that there is serious momentum to complete a deal on both sides of the negotiation, not that there is a completed deal at this point. So until there is further reporting, all we can do is speculate on what the terms of Connor’s extension will ultimately be.

Photos courtesy of Terrence Lee-USA TODAY Sports