The Winnipeg Jets are no longer a team coming off a Presidents’ Trophy season. They are a team that collapsed toward the bottom of the standings one year later despite employing a Hart Trophy-winning goaltender signed long-term at $8.5 million per season.
At some point, difficult questions stop being unfair and start becoming necessary.
How many versions of this core does Winnipeg need to see before admitting it may no longer be capable of competing for a Stanley Cup? How many seasons can the organization justify building around elite goaltending while the roster in front of Connor Hellebuyck continues to fall short when expectations rise?
That is the uncomfortable truth surrounding the Jets right now.
Hellebuyck is not your average, run-of-the-mill starting goaltender. He is a three-time Vezina Trophy winner, a two-time William M. Jennings Trophy winner, a Hart Trophy winner, and an Olympic Gold Medalist. He has played over 55 games in nine different seasons, carried one of the NHL’s heaviest workloads for nearly a decade, and consistently given Winnipeg a chance to compete regardless of what was happening in front of him.
And yet, the Jets still have one trip beyond the second round to show for it.
That is what makes a conversation surrounding Hellebuyck’s future so uncomfortable.
For years, Hellebuyck has masked flaws in Winnipeg’s roster construction. He has covered for defensive breakdowns, inconsistent secondary scoring, underwhelming special teams stretches, and nights where the Jets simply did not look like a legitimate contender. There were seasons where Hellebuyck was not just Winnipeg’s best player, but arguably the only reason the Jets remained relevant in the playoff race at all.
Eventually, organizations have to ask themselves whether elite individual talent is hiding larger structural problems.
The reality facing Winnipeg is brutal: the Jets may be approaching the point where keeping Hellebuyck satisfies the short-term goal of remaining competitive, but hurts the long-term goal of building a true Stanley Cup contender.
At 33 years old and signed through the 2030-31 season, Hellebuyck’s timeline may no longer fully align with where the organization is heading. Winnipeg’s prospect pipeline has thinned out, the roster lacks enough emerging high-end talent, and the franchise remains stuck in the dangerous middle ground between contending and retooling.
That is why rival teams are watching Winnipeg closely.
Elite franchise goaltenders rarely become available, especially ones with Hellebuyck’s resume. Teams spend years searching for stability in net, and if there is even the slightest indication that Winnipeg could consider a major organizational pivot, contenders across the league will line up to make offers.
The hardest question the Jets may eventually have to answer is not whether Connor Hellebuyck can still carry a franchise. It is whether continuing to ask him to do so is delaying the difficult decisions the organization should already be making.
What Could Winnipeg Realistically Target in a Deal?
If Winnipeg ever reaches the point where it seriously explores moving Connor Hellebuyck, the trade would immediately become one of the biggest franchise-altering decisions in Jets history.
It would not simply be about replacing a goaltender. It would be about choosing a direction.
Does Winnipeg attempt to remain competitive while reshaping the roster around younger talent? Does the organization finally embrace a larger reset? Or does management double down on a core that has repeatedly fallen short when expectations were highest?
Those are the questions attached to every potential Hellebuyck scenario.
Florida Panthers
If Winnipeg trades Connor Hellebuyck to Florida, the Jets would effectively be sending one of the NHL’s best goaltenders to a franchise that already solved the playoff puzzle Winnipeg has spent years trying to figure out.
If Florida seriously looks at acquiring Hellebuyck, it’s $1.5 million less than what Bobrovsky was making, and it gives them the necessary flexibility through the majority of each season.
Hellebuyck has played over 55 games in a season nine times in his career, and hit over the 60-game mark six times. Even with a minor knee surgery needed in the 2025-26 season, Hellebuyck still managed to play 57 games and be ready for the Olympics.
Florida is in a tight situation with a shallow prospect pool and limited picks to offer Winnipeg. Any package from Florida would likely need to begin with the ninth overall pick, while a young NHL-ready forward such as Mackie Samoskevich could help balance the return.
Florida also offers something Winnipeg has struggled to provide consistently throughout Hellebuyck’s career: proven championship stability.
Paul Maurice guided Hellebuyck to his lone conference final appearance before leaving Winnipeg and reaching three Stanley Cup Finals with Florida, winning twice.
In Hellebuyck’s case, Florida has a lot of familiar faces, so an adjustment period may be next to none.
For Winnipeg, that possibility would be difficult to stomach: watching one of the greatest players in franchise history join an organization that already became everything the Jets have spent years trying to become.
Los Angeles Kings
A trade with Los Angeles would force Winnipeg to confront a painful reality: the Jets may need to sacrifice elite goaltending in exchange for desperately needed young offensive talent.
The only immediate negative for Los Angeles is having Anton Forsberg and Darcy Kuemper signed for another season, plus having three promising young prospects in Carter George, Erik Portillo, and Hampton Slukynsky.
The Kings own the 17th overall pick in the 2026 NHL Entry Draft, which will most likely be a key piece in the trade. Unlike Florida, Los Angeles has some significant assets that could entice Winnipeg to make a deal. One of Los Angeles’ top young players, like Quinton Byfield, would be sent the other way, and that fills an immediate need for Winnipeg while creating another.
The answer to what the Winnipeg Jets would face without Connor Hellebuyck came in the 2025-26 season: they simply weren’t good enough to compete.
Does Winnipeg take a veteran goaltender like Darcy Kuemper or Anton Forsberg in return to solidify their net? Or would Winnipeg run with a young goaltending tandem with one of their upcoming young goaltenders in Thomas Milic and/or Domenic DiVincentiis.
The most likely scenario would see Winnipeg take one of Kuemper or Forsberg in return, and in the case of Forsberg, that’s just a reunion between the two sides.
A deal with Los Angeles would signal that Winnipeg is finally prioritizing long-term roster evolution over trying to squeeze one more run out of the current core.
San Jose Sharks
San Jose represents the type of situation Winnipeg may secretly envy: a franchise with elite young talent, multiple premium assets, and a clearly defined long-term direction.
Adding a goaltender of Connor Hellebuyck’s stature would put an exclamation on the direction the Sharks are headed.
This is a team that has multiple needs, and goaltending isn’t its immediate need. Should the Sharks decide to upgrade in net, this would likely be a big trade for both the Sharks and the Jets that addresses needs on each team.
Like the Los Angeles trade possibility, Winnipeg would end up in a scenario where they end up with one of Alex Nedeljkovic or one of San Jose’s top goaltending prospects, Joshua Ravensbergen or Christian Kirsch.
Where San Jose has the upper hand is a premium prospect cupboard that has graduated into the NHL, and two first-round picks in the 2026 NHL Entry Draft. This becomes an enticing trade possibility as San Jose has been known to be in the market for a defenseman, and Winnipeg has just that.
A trade with San Jose would not just represent a major hockey move for Winnipeg. It would represent an acknowledgment that the organization’s timeline has fundamentally changed.
Buffalo Sabres
Buffalo may be the most dangerous trade partner for Winnipeg because they can offer something the Jets are increasingly lacking: young NHL-ready talent capable of changing a franchise’s trajectory.
Buffalo represents the type of aggressive organizational gamble Winnipeg has struggled to make.
The Sabres are no longer rebuilding for the future. They are a team trying to take the next step now, and their playoff exit exposed a reality the organization can no longer ignore: instability in net may be the biggest thing standing between Buffalo and legitimate contention.
That is what makes Connor Hellebuyck such a fascinating possibility.
Like the San Jose scenario, this would not simply be a Connor Hellebuyck-for-Owen Power framework. Winnipeg is already log-jammed defensively, and bringing in another high-profile defenseman without moving out significant pieces elsewhere creates another problem entirely.
Buffalo would also need to make difficult decisions in goal, whether that involves Ukko-Pekka Luukkonen, Devon Levi, Alex Lyon, or some larger restructuring of their crease altogether.
But unlike some of the other teams connected to Hellebuyck speculation, Buffalo possesses the type of young NHL-ready talent and organizational flexibility that could force Winnipeg to seriously consider whether accelerating a larger reset makes more sense than continuing to hold the line with the current core.
The Question Winnipeg Can No Longer Avoid
Connor Hellebuyck has already done everything an organization could reasonably ask from a franchise goaltender.
Three Vezina Trophies. A Hart Trophy. Two Jennings Trophies. An Olympic Gold Medal.
Nearly a decade spent carrying one of the NHL’s heaviest workloads while repeatedly keeping the Winnipeg Jets relevant through inconsistency, roster flaws, and seasons that could have fallen apart without him.
And yet, for all the individual greatness, the Jets still have one trip beyond the second round to show for it.
That is what makes this conversation so uncomfortable.
The longer the speculation surrounding Hellebuyck continues, the less it becomes about whether he is capable of carrying the Jets. He has already answered that question countless times throughout his career.
The real question is whether the Jets are still capable of building a roster worthy of one of the greatest goaltenders of his generation.
Because at some point, continuing to rely on Connor Hellebuyck to erase larger organizational problems stops being sustainable. Eventually, a franchise has to decide whether it is truly close enough to contention to justify holding onto a player of his caliber, or whether refusing to confront that reality only delays the difficult decisions that should already be happening.
And if Winnipeg cannot answer those questions honestly, the trade speculation surrounding Connor Hellebuyck is only going to grow louder.
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