Connor Hellebuyck’s future could be determined by the end of the week, the Winnipeg Jets might acquire a second-line centre and there are enough teams putting draft picks in play for Kevin Cheveldayoff to move the No. 8 pick, acquire a second top-10 pick or both.The business end of the offseason began with multiple blockbusters over the weekend and the range of outcomes for Winnipeg’s week ahead is wide. Here’s what we’re hearing about the Jets’ offseason priorities, with Hellebuyck’s future up in the air and Round 1 of the draft coming up on Friday — plus contract needs, long-term thinking and more.1. Pick a laneWe’ll make room for a single, big-picture theoretical concern. When does this team win?Are the Jets trying to compete for the Stanley Cup next season, trying to make the playoffs, or trying to set the table for some kind of future glory?If the goal is to make the playoffs and hope for the best, then the task seems straightforward: upgrade the second line, appease Hellebuyck and run it back. A lot went wrong for the Jets last season; they were old, slow and injured, while Hellebuyck struggled and the power play got stagnant. Some of that is redeemable via regression, while a second-line upgrade could easily take care of the rest.If the Jets believe they can win the Stanley Cup as they’re built today, they’re wrong. Playoff success might be attainable with targeted upgrades and challenging a roster rich in 2025-26 underachievers to prove themselves worthy of midseason additions. The challenge is gargantuan — Colorado, Minnesota and Dallas are still great teams and Utah is on pace to join them — but at least Winnipeg’s midseason moves would be tied to its own performance.Trading Hellebuyck would yield multiple assets and constitute a retool, whatever the return — and it’s a distinct possibility.How to win a Stanley Cup without superstarsHarman Dayal2. Appease (or offload) HellebuyckMy understanding is that the Jets are open to moving Hellebuyck, Hellebuyck is open to being moved, and nothing will happen unless Winnipeg gets what it considers to be a satisfying return. This could be a second-line centre and a bigger defensive defenceman, along with draft capital — but there are some compounding issues.The return will depend on the degree to which the Jets can establish a bidding war for Hellebuyck. He’s on the shortlist for best goaltender in the world, has an affordable $8.5 million cap hit and he’s in a market that sees several contenders in need of goaltending help, Florida chief among them. The Panthers have approximately $7 million in cap space, even after acquiring Brady Tkachuk — more than enough to acquire Hellebuyck if Anton Lundell is part of the deal.Will a bidding war get “stupid,” as one front-office source suggested to us last week?Florida’s Tkachuk blockbuster on the heels of shipping Mackie Samoskevich to Seattle takes multiple potential assets off the table for Winnipeg. Not only do the Ottawa Senators now own Florida’s No. 9 pick, but also the Panthers have traded all of their first-round picks until 2030. The one prize that remains is Lundell, a 200-foot centre with four years left on his $5 million AAV deal, who scored 18 points in 23 games when Florida won the 2025 Stanley Cup. Perhaps a trade involving Lundell, a depth centre like Evan Rodrigues, and a second-round pick is more palatable to Florida than Lundell and No. 9 overall would have been.Florida isn’t the only potential suitor, of course, but they’ve just added one Olympic gold medalist and don’t have a goaltender on their roster at the moment. The Pittsburgh Penguins, Vegas Golden Knights, Buffalo Sabres, Edmonton Oilers and Utah Mammoth are five playoff teams who need help in net, while there are cases for the New Jersey Devils, Seattle Kraken and Detroit Red Wings to upgrade, too.If the Jets can manufacture a bidding war, then the poor UFA market, increased salary cap and Hellebuyck’s Olympic gold medal should maximize his value. If a team like the Panthers were ever to believe they were the only bidders (or atop a small list of serious contenders) then the impetus to make their most appealing offer would diminish.One final note: Neither the Jets nor Hellebuyck have said anything they couldn’t walk back if Winnipeg deemed the trade returns inadequate. This is vital. It is still theoretically possible for the Jets to retain Hellebuyck and for everyone involved to downplay the seriousness with which they’re recruiting calls. The only thing the Jets can’t afford to do is let the situation drag into the regular season. On-again, off-again relationships seldom work in the long run.3. Make (or trade) the No. 8 pickThe simplest and therefore most likely outcome is for the Jets to make their pick at No. 8. (Obviously, a Hellebuyck trade would change this outlook.)I think Jets brass would be thrilled if Daxon Rudolph is available at No. 8. I think Alberts Šmits and perhaps even Keaton Verhoeff would also be seen as wins, putting the Jets in a good position to wait and see how the board plays out before committing to their pick. Perhaps even more intriguing? Orchestrating the homecoming of left-shot defenceman Carson Carels.Carels, a product of Cypress River, Man., is a big, physical player with top-pairing, tough-minutes upside. His physicality and competitiveness are elite, his skating is excellent and he has enough offence to contribute at five-on-five (although he’s not quite seen as a power-play quarterback). It’s unlikely he’ll be available at No. 8, but there’s appeal in moving up to take a local product who’s balancing draft prep with calving season. Carels’ local ties might make him more amenable to signing a long-term extension when the time comes.If Winnipeg is open to trading their pick for immediate help, then last summer’s transactions offer two templates for adding top players. Carolina acquired K’Andre Miller on July 1 for a top-10-protected 2026 first, a 2026 second and defenceman Scott Morrow. A few days prior, Montreal acquired Noah Dobson at the 2025 draft for Emil Heineman and the No. 16 and No. 17 picks in 2025.Our offseason trade board is stocked with talent in a way the UFA board is not; options without trade protection include Matthew Knies, Mason McTavish, Simon Nemec, Jason Robertson and Shane Wright. (If Robertson were uninterested in a sign-and-trade to Winnipeg by way of replicating the Miller deal, then the Stars’ 24-year-old centre Mavrik Bourque would be interesting all by himself.)4. Get far, far ahead of Morrissey’s and Samberg’s next contractsHellebuyck is drawing so much immediate focus that it’s easy to forget Josh Morrissey and Dylan Samberg are scheduled to become free agents in 2028.Given that Morrissey and Samberg will each be eligible to sign extensions as soon as July 1, 2027, the Jets’ success in 2026-27 may have an outsized impact on their futures. I would suspect the Jets view Morrissey as an established part of their iconography — there’s no risk of Winnipeg forgoing a full-court press to retain him for the duration of his career. They’re likely to view Samberg that way by the time his contract is up, too, but weren’t able to agree to terms on a long-term deal last summer. He’s scheduled to become a relatively young UFA (29 in 2028) and continued growth should earn him a big raise at that time.There’s nothing imminent available, but proactive communication was part of the Jets’ success in retaining Kyle Connor — all the more critical after losing Nikolaj Ehlers for nothing last summer. Winnipeg can’t afford to replicate Ehlers’ free departure and will want to get far ahead of Morrissey’s and Samberg’s next deals.5. Sign Perfetti and RosénCole Perfetti is Winnipeg’s top restricted free agent this summer and the only one with arbitration rights. Players have until 4 p.m. CT on July 5 to file for arbitration, with hearings taking place sometime between July 20 and Aug. 4.Even if Perfetti files for arbitration, I don’t think anyone involved will want a hearing to take place. All three of Samberg, Gabriel Vilardi and Morgan Barron filed for arbitration last summer and all three signed prior to their hearings. I wouldn’t be surprised if Perfetti’s contract gets signed on a similar timeline, with no party looking to recreate the grinding process of arbitration Andrew Copp went through in 2019. The challenge is picking the right contract term and setting the right price.Perfetti, 25, is two years away from UFA eligibility. His most recent season — 32 points in 68 games — is not compelling enough to get him into Mason McTavish ($7 million AAV) or JJ Peterka ($7.7 million AAV) territory. Perfetti’s camp could argue that his high ankle sprain let the air out of his numbers, drawing attention to the 50 points in 82 games he scored in 2024-25. It would be a reasonable argument and a more accurate reflection of Perfetti’s ability, but recency matters.There might be impetus for Perfetti to sign a one-year contract and bet on himself, thinking he can put together a more impressive year heading into a fresh set of negotiations next summer. There might be impetus for the Jets to lowball Perfetti on a long-term deal, trying to take advantage of his step back in point totals before he establishes himself as a consistent second-line scorer. The most likely outcome is somewhere in the middle.I think this ends with a four-to-six year contract somewhere between $5.5 million and $6.5 million per year. Don’t get worked up about reports that no contract is imminent; it is entirely expected and normal for the negotiation to take some time.Rosén does not have arbitration rights. His 11 points in 52 career NHL games should not make for a difficult negotiation, as excited about his potential as Jets fans may be.The Jets have other areas to work on this summer: upgrading their approach to development and analytics, and continuing to assess and evaluate the coaching staff. Scott Arniel will enter 2026-27 on the final year of a three-year deal. They spoke to Shane Doan, perhaps with player development and a path to management in mind, and I wouldn’t be surprised if fans — Mark Chipman among them — are interested in Jonathan Toews continuing with the organization in some capacity.Those can be July and August concerns. The Jets begin draft week in the position to make noise, whether their full set of fireworks ignites or not.