General manager Kevin Cheveldayoff and the Winnipeg Jets’ front office have a lot on their hands over the next two-and-a-half weeks.
Sure, they might kick back and enjoy the remaining game(s) of the Stanley Cup Final between the Edmonton Oilers and Paul Maurice’s Florida Panthers. But that’s not what we’re talking about here.

Photo by James Carey Lauder/USA Today
For Winnipeg, the summer of 2025 will be one that defines the direction and perception of the franchise for the perceivable future.
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Why is that, you ask?
Well, to put it bluntly, Chevy and Co. need to cough up some funds – and a lot of them, if they want to keep the current assembly of players together for next season and beyond.
Winnipeg, historically, has not been a prime destination for free agents in the offseason.
To be completely fair, Manitoba is hardly even a consideration by most star players looking to sign long-term, lucrative contracts for top dollar.
And it has nothing to do with the players, coaching staff, front office or management.
We are talking physical concerns with the weather and location.
Yes, it has been very difficult for Cheveldayoff and his team to attract suitors to come to the Canadian prairies, especially on long-term deals.
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That said, the Jets’ model has long been ‘draft and develop’.
It has worked wonderfully for the majority of the team’s active roster thus far:
Connor Hellebuyck, Mark Scheifele, Josh Morrissey, Adam Lowry et el are all Jets draft picks who have worked their way to NHL stardom. Others have joined the Jets by way of trade and have since realized the team makeup and success far outweighs the cold winter days. So much so that extensions have been put in place. Nino Niederreiter, Alex Iafallo, Vlad Namestnikov and Neal Pionk have each chosen to settle down in Winnipeg after beginning their careers in more desirable climates.
But now, back to business.
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The summer of 2025 will see a number of contracts handed out for 2025-26 and beyond. Winnipeg has five unrestricted free agents and four restricted free agents. Those five players no longer bound by contract under the Jets will be free to sign wherever they so choose come July 1.
The four others who have not yet earned signing rights will likely agree to terms with Winnipeg on contracts within July or August – Those players are less of a concern to Chevy, as the team and player typically do want to do business together and maintain a strong working relationship.
But it is the five UFAs that will be the biggest cause for concern.
Highlighting the list is star forward Nikolaj Ehlers. The 29-year-old left winger has concluded the final year of his seven-year, $42 million contract with Winnipeg and is set to test the waters in July.
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Unless Cheveldayoff can swoop in with an acceptable eleventh-hour offer, Ehlers is good as gone.
Has the Dashing Dane played his final game for the Jets?
It is beginning to look that way. The closer it gets to July without any sort of contract development, the more likely it will be that Ehlers chooses to part ways with the organization that drafted him ninth overall in the 2014 NHL Draft.
He has spent his entire 10-year career with Winnipeg, to which he has amassed 225 goals, 520 points and 222 penalty minutes in 674 regular season games. Ehlers has also added nine goals, 21 points and 10 penalty minutes in 45 postseason contests.
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Despite his versatility, crafty puckhandling and speedy zone exits/entries, Ehlers has never been relied on as a top-line player. He has been buried behind variations of Kyle Connor, Mark Scheifele, Blake Wheeler, Gabe Vilardi, Pierre-Luc Dubois, Cole Perfetti, Patrik Laine, Bryan Little and others over the course of his career, never quite landing those coveted top-line minutes.
Has his usage, lack of playing time, power play minutes and the Jets’ depth become too much to handle on a daily basis?
Does Winnipeg have a tight budget?
Are there other opportunities within the other 31 NHL clubs to which he could succeed in a top-line role?
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The answer to all of those questions is likely a resounding ‘yes’.
Dylan Samberg, Gabe Vilardi, Morgan Barron and Haydn Fleury are likely all contracts that Cheveldayoff will want to renew, and fast. But if he doesn’t find a way to make a little extra room in his budget for Ehlers, the quickest Jet that anyone has ever seen will no longer be dressed in polar night blue come October.
For a player of Ehlers’ skill set, paired with the fact that the salary cap will be rapidly rising over the next handful of years, on top of other comparable players and contracts offered, it is expected that Ehlers will earn $8-9.5 million annually on his next deal.
Signing for eight years with the Jets at $8.5 million would cost Winnipeg $68 million, but it would avoid the team needing to track down another top-six, power play specialist who can carry the puck with the best of them.
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Certainly Vilardi and Samberg are utmost priorities, but much like Mitch Marner in Toronto and Sam Bennett in Florida, some big-name players just stick out a touch more.
Right now, Ehlers is sticking out like a sore thumb. Before taking another shot at the lowly nail with his 12 oz. hammer, Cheveldayoff will need to assess the repercussions of his swing.
Quite often you think a lot more about the misses than the hits.
And when it results in a squashed thumb and a nail that will never quite grow back the same, it’s hard to get over.