The Winnipeg Jets face a franchise-altering decision regarding Connor Hellebuyck.Do they keep their franchise goaltender, who is on the short list for best in the world? Or do they cash in on a potential bidding war that his sudden availability would create?There are cases to be made for both courses of action.Hellebuyck’s contract provides outstanding value at $8.5 million average annual value, particularly in his league MVP-caliber seasons. Even when he’s merely in Vezina Trophy form, the 33-year-old delivers outstanding impact relative to his compensation. Now that he’s won an Olympic gold medal, Hellebuyck’s trade value should be at an all-time high.One front office source suggested the market for Hellebuyck “could get stupid.” If so, then Winnipeg’s most strategic play is to use Hellebuyck’s peak, medal-winning value to address longstanding roster holes — second-line centre, top-four defenceman — once and for all. If Hellebuyck’s best seasons win awards in Winnipeg, then he must be capable of winning a championship behind an elite defence corps, as he did for Team USA.Which is also the argument for why the Jets should keep him. The Jets have three star skaters — Mark Scheifele, Josh Morrissey and Kyle Connor — and Hellebuyck’s best seasons have contributed more to team success than any of them. Hellebuyck would be the best player in any Hellebuyck trade, and, as the adage goes, if you lose the best player, you’ve lost the trade.But we know teams are calling Winnipeg about Hellebuyck in the wake of his heated exit interview. We believe Kevin Cheveldayoff is taking those calls seriously.How to win a Stanley Cup without superstarsHarman DayalSo what should the Jets do about it? Here are the five best reasons to trade him, three good ones to keep him and one ultimate conclusion.Trade Hellebuyck: The presumed bidding warThe Florida Panthers and Buffalo Sabres are two of several playoff-caliber teams who need a goaltending upgrade. Florida doesn’t have a goaltender under contract next season, with 37-year-old Sergei Bobrovsky’s future still up in the air.Our panel of NHL sources recently graded a subscriber’s proposal of Hellebuyck for Anton Lundell and the No. 9 pick as legitimate. The move would give Winnipeg a capable, cost-controlled, 24-year-old centre in Lundell and the opportunity to make back-to-back selections inside the top 10 (or a follow-up trade, using the Panthers’ pick). Other intriguing Panthers without trade protection include 23-year-old restricted free agent Mackie Samoskevich and 6-foot-6 defensive defenceman Niko Mikkola.Buffalo is most exciting on defence, where Rasmus Dahlin leads a group of stars that includes 23-year-old Owen Power. If the Sabres were amenable to moving Power, he’d be among the top potential returns, while RFA forward Peyton Krebs is also of interest.We don’t know that teams are leading with this quality of offer — just that the list of teams that need help is long. You can add the Pittsburgh Penguins, Vegas Golden Knights, Edmonton Oilers and Utah Mammoth to the list of playoff teams that need help in net, along with the San Jose Sharks, Seattle Kraken, Toronto Maple Leafs, New Jersey Devils and perhaps even the Detroit Red Wings. The trade return could include help for the second line, a boost on defence and at least one first-round type of asset.Keep Hellebuyck: Who plays goal?Winnipeg can’t hand its net to prospects Dom DiVincentiis and Thomas Milic and sell itself as a playoff team. The UFA market is not inspiring, with Bobrovsky, Stuart Skinner and Frederik Andersen the top goalies on our free-agent big board.Could the Jets make a trade to San Jose that involves 24-year-old Yaroslav Askarov? Maybe, but Askarov is a career .887 goalie. Any bet on him, Buffalo’s Devon Levi, 24, or Detroit’s Sebastian Cossa, 23, is a gamble. Hellebuyck’s 24-year-old season was 2017-18 — his breakout year. Those prospect goaltenders may go on to great careers, but they have 103 career games combined, with sub-.900 save percentages.Could Winnipeg cobble together a tandem with some combination of free agents such as Bobrovsky, Skinner, Connor Ingram or Eric Comrie? Unheralded goaltenders have won Stanley Cups as recently as Sunday, with top teams such as the Carolina Hurricanes favouring time-shares as opposed to clear No. 1 arrangements. Winnipeg would need a goaltender in its initial trade or in a follow-up, lest it commit to the idea of punting 2026-27 in the name of another high draft pick.Trade Hellebuyck: He’s a depreciating assetThe three-time Vezina Trophy winner and 2025 league MVP has arguably been the best goaltender of his generation, even if Hellebuyck’s dependence on play reading and relative lack of acrobatics can lead to underappreciation. But Hellebuyck is 33, just posted an .895 save percentage in the NHL and missed a month with a knee issue and ensuing surgical procedure. Time is an issue.Could be Hellebuyck’s down season is a blip and he ends up dominating again in his mid-30s; Dominik Hašek and Tim Thomas each won Stanley Cups at 37. Time catches up to everyone, though, and more recent NHL greats such as Carey Price and Henrik Lundqvist saw steep declines in their mid-30s. It would be best for Winnipeg to move him while his value is at its peak.Trade Hellebuyck: Demands from high-stakes stars lead to Cheveldayoff’s best workRequest a trade from Winnipeg, history tells us, and Cheveldayoff will win the trade. If Hellebuyck is truly unhappy — and that “if” is important, given the lack of clarifying comments from him, his agent or the Jets — then Cheveldayoff might be forced into the exact situation in which he’s always done his best work.The Jets’ last great trade was a disgruntled Pierre-Luc Dubois to the Los Angeles Kings for Gabriel Vilardi, Alex Iafallo, Rasmus Kupari and a second-round pick. Cheveldayoff’s other career highlights include the initial Dubois trade, acquiring him and a third-round pick for Patrik Laine and Jack Roslovic — each of whom had made trade requests.Keep Hellebuyck: He’s literally your best playerThere’s a scenario wherein Winnipeg trades Hellebuyck and acquires a second top-10 pick in this summer’s draft, while also increasing its odds of a lottery pick next summer. It would punt the 2026-27 season, putting strain on star scorers such as Connor and Scheifele (and 2028 UFAs Morrissey and Dylan Samberg). If Winnipeg pulled it off and kept its top skaters, it would be a relatively fast retool. It’s easier to imagine them being competitive in 2027-28 and beyond.But the easiest way to imagine Winnipeg being competitive is with Hellebuyck in goal.Keep Hellebuyck: He starred in the big gameNikolaj Ehlers’ instant Stanley Cup win follows back-to-back championships for Paul Maurice with the Panthers. As much as I believe that Maurice’s time in Winnipeg had come — an assertion he made himself when he stepped down — it’s clear you can win with anybody if your team is good enough.If Winnipeg could rebuild its second line and add a superb top-four defenceman, they’d be better off with No. 37 in goal. It’s true that Hellebuyck has been rattled in previous playoffs, but the Jets’ net-front defence was awful against the Colorado Avalanche and struggled against the St. Louis Blues and Dallas Stars. Hellebuyck played so well in the biggest game of his life that he became the story in Team USA’s gold medal win over Canada in Milan. Shouldn’t that be enough to believe he can do it in the NHL?Trade Hellebuyck: Playoff hockey is different than the OlympicsIt isn’t hard to look at the way teams bulldoze their way to the net during the Stanley Cup playoffs, creating the kind of chaos Hellebuyck hates, and conclude it’s a different style of hockey than the Olympics.If Hellebuyck’s greatness depends on the speed and accuracy of his reads — the best play-predicting brain in the world — then I have some time for the idea that the NHL playoffs are built to cause him trouble. He dominated the Oilers in the 2021 playoffs, playing some of the most spectacular hockey of his career against Edmonton’s speed and skill, but the last time Winnipeg offered Hellebuyck great net-front defence in the playoffs was during Dustin Byfuglien’s heyday. The net-front violence of playoff hockey may make Hellebuyck unusually vulnerable behind the Jets’ current defence.Trade Hellebuyck: If he wants to go, let him goHellebuyck is under contract for five more seasons. If Winnipeg wants him to be its goaltender, all it has to do is avoid making a trade. Hellebuyck would be forced to play for Winnipeg or for no team at all, and it’s hard to win a Stanley Cup that way. (If he’s happy, then, of course, none of that is an issue.)But the hardball would be a distraction. It would make Winnipeg worse on the ice for the duration of Hellebuyck’s absence. And, even though an unhappy Dubois was a viable second-line centre for most of his Jets career, I just don’t think disgruntled franchise cornerstones are tenable long term. If Hellebuyck has lost faith in Winnipeg’s ability to win, then I can’t imagine the summer of transactions that would permanently re-establish that faith. Winnipeg can’t afford to place itself at the whims of any individual player’s assessment of its Cup readiness.Before this season, all of Winnipeg’s winning ambitions depended on Hellebuyck in goal. He’s still the Jets’ top player. If they had a realistic path toward a Cup-contending roster with him on board, it would be paramount that they keep him.But it’s hard to chart that path. It’s also more conceivable that Winnipeg trades its star goaltender and survives on average goaltending than for it to move someone such as Scheifele or Morrissey and then replace him with an outside hire. If Hellebuyck is focused on the Jets, he’s theirs to keep. If he’s focused on the Cup, then his ambition and the pressure he’s put on Jets management are a gift to a franchise that needs to retool.