The Winnipeg Jets have a strong but imperfect core group of players, led by Connor Hellebuyck, Josh Morrissey, Mark Scheifele and Kyle Connor — in that order. The Jets do not have an obvious next wave of elite talent, nor is their roster deep in game-breaking talent beyond the aforementioned core.

It is difficult to chart their route to the Stanley Cup.

If there was hope on Monday that Kevin Cheveldayoff or Scott Arniel would offer clarity to that route, they did not share it with reporters at Canada Life Centre. Instead, it seems as though the same people will enact the same processes, searching for the same answers — a second-line centre at minimum — with the same depleted asset pool, drained by multiple seasons of trading draft picks for veterans who signed elsewhere as free agents.

How did the Jets go from Cup contenders with an elite collection of young talent in 2018 to this year’s mess — with last year’s Presidents’ Trophy as a thrilling diversion? What could put the existing core over the top before they’re too old to handle their part of the bargain?

This is the story of a hockey team stuck in the “mushy middle” — too good to tank, too flawed to win — without an obvious route out.

The 2026-27 Jets’ starting point

This 2026-27 Jets roster includes all veterans under contract, plus young NHL players like Brad Lambert and Isak Rosén and prospects like Danny Zhilkin and Nikita Chibrikov — all of whom will require waivers next season:

LWCRW

Kyle Connor

Mark Scheifele

Gabriel Vilardi

Isak Rosén

Cole Perfetti

Brad Lambert

Morgan Barron

Adam Lowry

Alex Iafallo

Cole Koepke

Vladislav Namestnikov

Nino Niederreiter

Nikita Chibrikov

Danny Zhilkin

LD

RD

Top prospects

Josh Morrissey

Neal Pionk

Brayden Yager

Dylan Samberg

Elias Salomonsson

Sascha Boumedienne

Haydn Fleury

Dylan DeMelo

Colby Barlow

Kieron Walton

G

Alfons Freij

Connor Hellebuyck

Kevin He

The second line needs a massive upgrade. Winnipeg got six points in 25 games from Lambert and three assists in 21 games from Rosén this season. Cole Perfetti produced like a 50-point player down the stretch, which is enough to rekindle hope for a strong season next year, but not so much that he can be thought of as a surefire driver with two inexperienced linemates.

The first line is kept intact because Arniel told me on Monday he didn’t think splitting Connor and Scheifele would be a long-term solution.

“(We were) having a tough time scoring goals,” Arniel said. “Now I’m going to take away the line that actually can give me a chance to stay in a game, to win a game for us? Could I, should I? Maybe that’s part of what I will look at. And then it might happen next year. I really, really hope it doesn’t, but I don’t know.”

This forward group needs Adam Lowry to bounce back from one of the least effective seasons of his career. He didn’t perform like a shutdown stalwart following his return from hip surgery, losing too much explosiveness to control play at either end of the rink. Winnipeg’s third line only works if the $5 million AAV captain returns to form as a play driver.

On defence, the year is 2026 and Winnipeg still misses Dustin Byfuglien. I’ve rearranged the Jets’ lineup to promote Elias Salomonsson, projecting continued growth from the 21-year-old, and to demote Dylan DeMelo from the top pair. The Jets would ideally replace DeMelo on the top pair with a big, right-shot defenceman who can kill plays and move the puck well enough to contribute to offence — the best-case version of Salomonsson, who is still recovering from his concussion.

Route 1: Make the No. 7 overall pick

How do the Jets find the next Byfuglien (or, more realistically, a second-line centre)? The obvious answer is to trade their first-round pick: No. 7 overall heading into the May 5 draft lottery.

It’s also the wrong answer. Winnipeg is not a premier UFA destination. Cheveldayoff said he tried “like hell” to make trades to upgrade this year’s team; Winnipeg getting stymied by no-trade clauses is an old, oft-repeated story. The Jets’ No. 1 route to top-end talent — and most importantly, top end talent that stays in Winnipeg — is through the draft. The Jets need to make the No. 7 pick and that pick needs to develop into an NHL player, whether they’re able to choose a big, talented, right-shot defenceman like Keaton Verhoeff and Daxon Rudolph or a top centre like Tynan Lawrence or Caleb Mahotra.

It seems possible that the No. 7 pick could be moved for a top young player on an entry-level or RFA contract. If the Jets managed to acquire a pending RFA like Leo Carlsson or Jason Robertson and then signed him to a long term contract, I’d walk back my caution. From here, it seems like the only realistic win is to make the pick. Two years of Dawson Mercer, Tye Kartye, or another middle-six centre with 2028 UFA rights would be a disaster next to several years of team control on a homegrown player.

But the 2026 draft pick can’t help this core!

Imagine preparing for a future beyond the prime years of Connor and Scheifele. If the only options are to win a Cup with this core or never, then the premise is flawed.

Route 2: Trade the Sabres’ 2027 second-round pick

“I think we’ve sent the most draft picks out the door to try to win,” Cheveldayoff said when asked about his commitment to winning with his existing core of players.

From the 2018 Western Conference final run to now, the Jets have made 40 draft picks — well short of the full complement of 56. I don’t know that a second-round pick and a top prospect returns a good second-line centre, but it might bring back a secondary scorer who can help the Jets win now more than young players like Lambert, Chibrikov, Colby Barlow or Sascha Boumedienne.

There’s some precedent for useful middle-six players. The Seattle Kraken recently acquired perennial 30-point forward Bobby McMann from Toronto for a second- and a fourth-round pick; McMann scored 14 points in 18 games for the Kraken down the stretch. Ottawa got 24-year-old defenceman Jordan Spence from Los Angeles at last year’s draft for a third- and sixth-round picks; Spence is delivering decent second-pair minutes for a playoff team. At that same draft, Washington acquired 23-year-old forward Justin Sourdif, from whom they got 31 points in 73 games in a middle-six role.

These are all incremental wins, but they’re still wins. Any viable middle-six or second-pair player — especially in that early 20s age range, with multiple years of team control — makes the Jets a better team. And even a 40-point player would have been Winnipeg’s fourth-most productive forward last season.

Route 3: Reimagine the approach to young players

Winnipeg drafts almost as many NHL players as an average team would with its draft picks. It doesn’t tend to help enough of those players find their way onto the Jets roster. Winnipeg has a well-established reputation of waiting longer to promote their players than other organizations do.

The Jets commit fewer resources to developing their players than some rival clubs, with top spenders employing skills development coaches throughout the summer their prospects can use at no charge. Prospect development is the purview of former Moose players Jimmy Roy and Mike Keane, the latter of whom was a longtime NHL player, winning three Stanley Cups. They prioritize communication and critical self-evaluation, but leave skill development to prospects’ existing clubs.

Winnipeg’s development program has not been a success in recent years. The Jets predetermined that Salomonsson was an AHL player this season, despite great AHL performance last year and superior play to veteran defencemen like Luke Schenn during his first call-up. Consider that 2017-2023 first-round picks Kristian Vesalainen, Ville Heinola, Chaz Lucius (retired due to Ehlers-Danlos syndrome), Rutger McGroarty, Lambert and Colby Barlow have scored six goals in a combined 172 games for the Jets. Perfetti’s 157 points in 290 games is a massive win by comparison.

“It’s not long ago, when we made the trade for Pierre-Luc Dubois for Vilardi, Kupari and for Iafallo, our depth in our organization did change,” Cheveldayoff said when asked about the Jets’ reputation for not developing their players. “But I can’t apologize for that. I can’t apologize for the fact that that depth probably helped us continue to move forward.”

“There is no development in Winnipeg,” is how one NHL source put it.

Route 4: What if the Jets did trade a core player?

Cheveldayoff was asked if he’d consider moving one of Winnipeg’s core players. He demurred.

“Every decision that I’m making is to try to push this group forward to try to win a championship with this group of players,” he said. “Whether it comes to a trade or whether it comes to a move, that’s what I’m doing. That’s why these guys signed here, that’s why they committed.”

Cheveldayoff opened up his playbook to Hellebuyck and Scheifele in 2023, signing his top players to matching seven year contract extensions after charting Winnipeg’s path towards a Cup in detail. It was an unusual move for a GM known for keeping information on a need-to-know basis, but it worked. It may be that some of his doubling down on the current core is follow-through on the promises and plans he shared at the time.

Cheveldayoff spoke for a while about the importance of the draft and then circled back: “To answer your question, (I’m) certainly open to talk about anybody. But anything we do is about making this group one step closer to winning a championship.”

What if the Jets traded Hellebuyck?

It’s tough to find a comparable trade here because it’s rare for a franchise goaltender to be moved. It seems as though Hellebuyck should be able to return a top-four defenceman or second-line centre, but there’s little precedent.

The Chicago Blackhawks’ acquisition of Spencer Knight and a top-10 protected first-round pick for Seth Jones doesn’t quite cut it; Knight was up-and-coming as opposed to a Hart Trophy winner. The Capitals’ acquisition of Pierre-Luc Dubois from Los Angeles for Darcy Kuemper isn’t quite it, either — Kuemper is a veteran but doesn’t match Hellebuyck’s resume.

Would the Florida Panthers pay Anton Lundell and the No. 8 overall pick? Would it be enough to satiate fans, if the Jets were then made to gamble by signing a lesser veteran UFA? It’s difficult to tell, but it’s the kind of trade a team would explore if it believed it could get premium value for their franchise goaltender and then backfill his role — or if it believed the goaltender wasn’t that good in the first place. I don’t think this is Winnipeg’s perspective.

What if the Jets traded Connor?

Winnipeg changed the way it does business, making Connor’s $12 million AAV contract buyout proof by paying $41 million of its $96 million in the form of signing bonuses. It gave Connor a full no-movement clause, like it had given Hellebuyck and Scheifele two years prior. The Jets are committed to this player and will not trade him at this stage of his career.

Still, there are precedents for elite scoring wingers returning major assets.

When Colorado traded Mikko Rantanen, it received Martin Necas and Jack Drury in a three-team trade. When the Hurricanes later traded Rantanen to Dallas, they got Logan Stankoven, two first-round picks, and two third-round picks. Rantanen is beyond Connor’s quality, but the Panthers acquired Matthew Tkachuk for a more comparable player in Jonathan Huberdeau, packaged together with MacKenzie Weegar. If Winnipeg were able to pull off a similar move to what Florida did, perhaps there is a more truculent top scorer available to them, with superior defensive impacts.

What if the Jets traded Morrissey or Scheifele?

Hellebuyck’s best years drive more wins than any other player available, but goaltending is volatile enough such that it’s at least possible to trade a goaltender, sign a replacement, and survive the aggregate. The same applies to a scoring winger like Connor, with minimal defensive impact. The Jets would immediately miss Connor’s 40 goals and 90-plus points but give a little less back the other way, too.

It’s hard to imagine Winnipeg moving Morrissey or Scheifele and coping successfully without them. The trade archetypes in this case tend to be something closer to “veteran No. 1C for young player who might become a No. 1C and a draft pick.”

In all four cases, the trade is viable if it helps the Jets and an awful idea if it hurts them. It’s difficult to imagine Winnipeg ever taking a proactive approach to this kind of trade, even as Cheveldayoff has knocked reactive versions of similar trades out of the park. But the Jets are stuck in the mushy middle in part because they do the same things over and over again. Looking in new directions is worthy of discussion.

“Margins in this league are very, very thin. Winning and losing in this league can be as easy as one goal,” Cheveldayoff said in a prepared opening statement.

It’s clear that running an NHL club, as Cheveldayoff has done since 2011, is dependent on similar margins. The Jets can’t reasonably acknowledge their disadvantages with respect to trades and UFAs in one breath and then leave any idea unexplored in their offseason review. They’re already at a structural disadvantage; they can’t afford to self-limit their already-thin margin for error.