Connor Hellebuyck has gone public with his trade request. Where do the Winnipeg Jets go from here?From the possibility of a training camp holdout and Winnipeg’s other goaltending options, to Hellebuyck’s impact on the Jets’ core players, and tough conversations about legacy and rebuilds, we’ve got you covered.Here are the biggest questions facing the Jets following Hellebuyck’s Thursday press release — and how Winnipeg can answer them.Does Hellebuyck’s request ramp up the pressure?Kevin Cheveldayoff’s 31 rival general managers did not log onto social media, read Hellebuyck’s prepared statement and gasp in shock. There’s simply no way for that to be the case after Hellebuyck’s private trade request, which he says he made “several months ago,” and Winnipeg’s ensuing exploration of the trade market.There’s an argument to be made that the timing of Hellebuyck’s message puts pressure on Winnipeg to act quickly. Hellebuyck clearly wants a resolution before training camp. Perhaps the hope is Cheveldayoff will be so frightened by the possibility of a holdout, or running Stuart Skinner with Thomas Milic or Domenic DiVincentiis to start the season, that he somehow feels compelled to take a lesser offer. That seems unlikely, given veteran backups like Connor Ingram, Cam Talbot and James Reimer are still looking for work.And no Hellebuyck trade will be won or lost in the first weeks or months of the season. Whether you believe in his gold-medal-winning ability or doubt him because of recent playoff runs, there is little difference between Hellebuyck’s impact on a Stanley Cup contender if acquired in October or in March. Presumably his goal — and his leverage does exist, via a no-movement clause — is to play for a great team. Are the Carolina Hurricanes, Vegas Golden Knights, Florida Panthers or Buffalo Sabres likely to miss the playoffs, as they’re built today, because they didn’t get a week or a month of Hellebuyck’s services?That’s not to say there’s no pressure at all. With Hellebuyck, the Jets are a middling team, likely to compete for a wild-card spot or miss the playoffs without being truly awful. Without Hellebuyck — and without the reinforcements available via trade return — the team’s odds of making the playoffs take a hit. As a team projected to be on the edge of qualification, the risks and rewards of a few standings points are higher for the Jets than the contending teams they’re dealing with.But none of that is new. If Cheveldayoff wants to be just as stubborn with Hellebuyck as he was with Jacob Trouba in 2016 or in trade discussions involving Patrik Laine or Pierre-Luc Dubois in the years since, he’s just as able to do so as he was last week. The incentives are the same as they’ve always been: get the best trade return possible for the Winnipeg Jets.Who are the options if the Jets are slow to make a trade?Winnipeg has three goaltenders under contract, aside from Hellebuyck and Skinner: Milic (23), DiVincentiis (22) and Isaac Poulter (24). Milic is the most experienced of the three, playing in three NHL games last season. He posted an .871 save percentage and did not win a game. DiVincentiis was excellent for Manitoba during the AHL playoffs, while Poulter was primarily an ECHL goalie.Milic and DiVincentiis are promising prospects who may have meaningful NHL careers. Entrusting 30-35 games to them at this stage would embrace a rebuild the Jets are seeking to delay or avoid.How does this affect Morrissey, Samberg and the Jets core?If Winnipeg is to hold on to any pretenses of being a playoff team, it needs to ace the Hellebuyck trade and keep its core intact. To that end, Josh Morrissey is indispensable — a No. 1 defenceman who can make an impact in all situations. He regularly receives Norris Trophy votes, produces points on the power play and at even strength, and is a central figure among Winnipeg’s leadership group.But his contract is up in two seasons. The Jets are unlikely to embrace a rebuild; they will try to retain him on another long-term deal. Will he stay? For that matter, what about Dylan Samberg, another top-four defenceman whose contract is up in 2028?Morrissey has previously expressed the desire to retire in Winnipeg, but winning must play a role.“When you’re 20 years old, you feel like you have an eternity in the league in front of you. As years go by, the reality is there’s less and less seasons to have an opportunity,” Morrissey told The Athletic in a recent interview. “But, at the end of the day, I can speak to my opinion on this organization and team. I feel like we have a chance to get back to where we were a year prior and back to competing with the league’s best and have a chance to compete again for the Stanley Cup. As a player, that’s all you can really ask for.”It sounds as though Morrissey can empathize with Hellebuyck’s position but does not share it. He’ll be 33 when his contract ends, though — the same age Hellebuyck is now — and we’ll have plenty of time to evaluate his future. Mark Scheifele, Kyle Connor and Gabriel Vilardi are signed long-term and a great trade return could restore Winnipeg’s playoff hopes. It’s fair to wonder how closely winning will be tied to Morrissey and Samberg’s decisions in 2028.It’s also possible that other star players ask out should the Jets fail to build a winner, but there are no indications of anybody following suit at this time.Does this change Hellebuyck’s legacy with the Jets?The initial response to Hellebuyck’s trade request has not been positive. Some fans perceive his intentions as less to do with winning the Stanley Cup and more to do with getting out of Canada. Theories about Team USA’s collusion to get American stars to American cities will persist, particularly after Brady Tkachuk’s trade to the Florida Panthers earlier this summer. At the moment, there’s no evidence to support those theories — just Hellebuyck’s message that “moving on is the best path forward for me and my family.” The lack of explanation may be cold comfort.In 2023, Hellebuyck framed his long-term extension as the product of Winnipeg’s commitment to winning. At his exit interview in April, he openly doubted the Jets’ ability to build a contender. His desire to play elsewhere may be as simple as frustration at the difference between expectations and reality. Until Hellebuyck himself offers clarification, speculation will persist.Some fans will be swayed by the reason he gives, if he gives one at all. In the meantime, his on-ice accolades are many — three Vezina Trophies, one Hart, two Jennings and his name on almost every franchise goaltending record. His playoff record is decidedly mixed, with greatness against Edmonton in 2021, quality throughout most of Winnipeg’s 2018 run and more recent disappointment.Is Cheveldayoff’s legacy at risk, too?Cheveldayoff’s track record in the “trades he should lose” category is excellent. He’s well-practiced in making trades with little leverage, whether with Trouba, Laine, Dubois or Andrew Copp, and emerging with Winnipeg in solid position. If he fails to “win” this trade, it won’t be enough to sully his record in similar situations.But the chapter of Jets history that comes next should absolutely put Cheveldayoff’s legacy at risk. His best work has been reactive, not proactive. Winnipeg’s intent to avoid a rebuild will either work, earning him praise, or prove to be an exercise in futility, prolonging the pain of transformation as opposed to avoiding it. It’s possible that he’s arriving at the concept of a Hellebuyck trade too late, with diminished value a season after the 2025 Hart Trophy win, and may do so with respect to Scheifele, Connor and Morrissey in turn.“The plan is still to win,” Cheveldayoff said this summer. If he succeeds in that, his legacy is safe, regardless of trade outcome. If a rebuild arrives, imposed upon Winnipeg against its manager’s will, then Cheveldayoff must be held accountable for making a difficult situation worse. So too should Jets ownership, given their support for this route.In the meantime, Cheveldayoff will do what he’s always done in these situations: work at his own pace, as fastidiously as possible, looking for solutions to difficult problems.