Even Winnipeg’s wins leave them with all with kinds of difficult questions.

Winnipeg’s 2019 playoff nemesis, Ryan O’Reilly, was traded to Toronto. Homegrown talent Jonathan Toews won’t be traded at all; he hasn’t played for the Blackhawks since before the All-Star break and announced Sunday that he’s dealing with Long COVID symptoms and Chronic Immune Response Syndrome.

Timo Meier was always this trade deadline’s biggest and most obvious target; now the 26-year-old Sharks forward stands alone atop the list of available impact players.

How much should the Jets be willing to pay for him, Jakob Chychrun or any of the players who could help the team mount a playoff run?

Meier is a player we’ve discussed for the Jets at length: a point-per-game power forward who uses his size and speed to take the puck to the most dangerous areas of the ice. He’s well-known to several current Jets, including his former junior teammate, Nikolaj Ehlers, and former Sharks teammates, Dylan DeMelo and Brenden Dillon. Meier’s $6 million cap hit is also well within the range of what Winnipeg can afford now, with the Jets one of just a few teams capable of accommodating his $10 million qualifying offer — if Pierre-Luc Dubois indicates a desire to move on.

Winnipeg could also explore a long-term extension below $10 million or even move Meier in the offseason if they can’t convince him to stay. When a prime-aged player is that good, the options are plentiful — it’s one of the many items that make Meier or Chychrun more appealing than, say, Patrick Kane.

I recognize that connecting the biggest and most exciting names to Winnipeg feels counter to some fans’ expectations. The Jets followed a three-game winning streak with two losses to Columbus and New Jersey, while Monday’s 4-1 win took 50 saves from Connor Hellebuyck. Colorado is nipping at the Jets’ heels and there’s a chance the narrative shifts away from “can they catch Dallas for first in the West?” and toward “can they hold onto their wild-card spot?” Emotions are high in the post-All-Star break, pre-trade deadline world, and the power play against Columbus and puck management against New Jersey and New York have asked questions of Winnipeg’s quality that the Jets need to dig deep to answer.

Fans will also remember the time Kevin Cheveldayoff pulled the previously undiscussed Paul Stastny trade seemingly out of nowhere, finding a nearly perfect fit for the Jets’ 2018 stretch run. That was in the midst of Winnipeg’s push to compete for the Stanley Cup; Winnipeg traded its first-round picks in 2017, 2018 and 2019 in the name of securing its competitive window. Yes, the Jets’ 13th pick (which became Nick Suzuki) returned the 25th pick (Kristian Vesalainen) by trade and yes, Winnipeg got its own 2019 first-round pick back from New York but it cost the Jets defenceman Jacob Trouba. Cheveldayoff did what he could to slow the drain of draft capital but he couldn’t stop it altogether. Winnipeg wanted to “win now.”

To that end, I think Cheveldayoff’s biggest decision to make is how much of Winnipeg’s future he’s willing to sacrifice to chase a deep playoff run.

Winnipeg is good but not dominant, a virtual playoff lock and a tough out against any opponent but not a surefire contender. We’ve dug through the pieces and concluded that they can wear the contender label this year in a wide-open Western Conference, but the Jets lag behind the top teams in the East and behind Cup winners from most of recent history.

What is Cheveldayoff supposed to do with that?

In a typical year, the ideal play might be to supplement his team with veteran depth pieces — perhaps a third-line forward with enough quality to play up the lineup in a pinch and a second- or third-pairing defenceman. Stay out of the Meier aisle, protect the prospect pool and pay a more modest price to supplement Winnipeg’s biggest difference-makers — Hellebuyck, Josh Morrissey, Mark Scheifele, Dubois, Kyle Connor, Ehlers and Blake Wheeler. Six out of those seven players are young enough to bet on to do it all again next year.

But Winnipeg is well aware that this is not a typical season. Scheifele, Wheeler and Hellebuyck are scheduled to become free agents in 2024 and Dubois can join them by filing for arbitration or signing his qualifying offer (again.) If the Jets risk losing any of these players then they may look at moving those players this summer instead of losing them for nothing in 2024. (Dubois seems most likely but dare yourself to imagine a Jets landscape without Hellebuyck, the perennial Vezina Trophy candidate who stole Winnipeg’s win in New York.)

That puts Cheveldayoff in a quandary, a dilemma, a state of perplexity.

His scouts built this team. His efforts to protect Toby Enstrom from Vegas and to acquire Stastny, Kevin Hayes, Cody Eakin, DeMelo, Dillon, Nate Schmidt and other useful players hurt his prospect pipeline. Now that Chevelayoff’s more recent work has finally restocked that pipeline with top-end talent — Cole Perfetti, Chaz Lucius, Rutger McGroarty, Brad Lambert — those are precisely the players teams like San Jose should covet for a player like Meier.

Perfetti’s name may seem incongruous with the rest, given he’s scored 30 points in 51 games — a 48-point-per-82-game pace — as a 21-year-old rookie. He’s established himself as an NHL player and is tracking similarly to former Jets centre Bryan Little in terms of early career performance. He’s exactly the sort of player that Winnipeg has held onto in the past, protecting its stake in the future, ahead of former Jets like Jack Roslovic at the same age. He’s also injured right now, as Bowness announced on Monday.

Perfetti is not a power forward or an established NHL star; he’s a creative, highly intelligent player who processes the game faster than most players do. His ceiling is thought to be a first-line winger who can help (or even lead) a first-unit power play. I don’t see him putting a team on his back the way Meier can through his unique combination of speed and power, but I do see him having a substantial impact as a top-six player.

He’s not so good that I’d hesitate to trade five years of Perfetti for five years of Meier but that’s not the ask, is it? Meier is just like Dubois in that he could become a free agent as soon as 2024 if he signs his $10 million qualifying offer this summer. (In the theoretical world where Dubois signs a long-term deal this summer and Meier wants out, the Jets could simply not qualify Meier, making him a free agent in 2023.) Meanwhile, Perfetti is under team control until at least 2028.

I suppose the Jets could trade a player with Perfetti’s promise if they have an extension lined up for Meier but, if I’m Meier, I take my $10 million and see what the world has to offer me in 2024. That’s not meant as a slight to Winnipeg — a city I know and love better than Meier ever will — it’s just good economics.

That’s why, as much as I think it makes sense for Nick Kypreos to theorize about Perfetti (as he did in the Toronto Star this weekend), I absolutely do not see the Jets trading their 21-year-old rookie.

But if it’s not Perfetti, then is it Lambert, Lucius or McGroarty?

That’s the sort of dilemma I think Cheveldayoff is in with the trade deadline less than two weeks away. In any other year, the sensible thing might be to tinker or stand pat in the name of widening Winnipeg’s long-term window. This year, with this Western Conference, with that 2024 UFA situation facing the team? There’s nothing ordinary about it.

(Photo of Cole Perfetti: Kyle Ross / USA Today)

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