Winnipeg Jets' Stanley Cup contender checklist: Greatness beyond reach, future in doubt

Despite a 103-point season, Mark Scheifele's age is likely to catch up with him sooner rather than later. Cameron Bartlett / Getty Images Whenever a team falls from grace, there's always a fair share of blame to go around. The Winnipeg Jets went from winning the Presidents' Trophy one year ago to falling outside of the playoff picture altogether. There are layers behind this slide down the Western Conference standings, but one reason stands out above the rest: roster strength. Had Winnipeg at least crashed out and landed a top-five pick, maybe this season's struggles would have been worth it. Some lottery luck can go a long way in rejuvenating a team. Instead, the Jets' disappointing season earned them the No. 8 pick. Pair that with management's passive tendencies and overall track record, and this team could be on track to return to what has generally been its sweet spot: the mushy middle. Here's where the Jets stand going into the 2026-27 season, using the Cup Checklist. All projected values are age-adjusted based on each player's profile of comparable peers. The Jets live and die by Connor Hellebuyck, who has been their ace throughout this core's era. His 2025-26 season wasn't perfect, but he has a long track record of being this team's backbone in the regular season. The real issue over the years has been his playoff pedigree, but his play in the second round last spring and at the Olympics proved that he can raise his game in big moments. The team, especially at this point in his career, just has to manage his workload to keep him fresh for the playoffs. Josh Morrissey adds strength to the back end as an elite No. 1 who thrives on both ends of the ice. His age, similar to Hellebuyck's, does add a little urgency to this situation. Morrissey and Hellebuyck should have years of difference-making play ahead of them, but it's still worth keeping in mind that two cornerstones are in their early 30s. Kyle Connor's offense makes him a passable star forward. Some defensive improvements have made him less of a liability in his own zone, too. With a stronger cast around him, there's the potential to push the bar higher. Between Gabriel Vilardi, Cole Perfetti and Adam Lowry, there's some support in place behind Connor -- just not to the degree a contender needs. And Scheifele, who was the best forward on the team in 2025-26, falls short of the impact needed as a franchise forward. That's where age again creeps back into the conversation in Winnipeg, and why he slides down to the scoring forward role on the checklist. Even if Scheifele outperforms that designation this season, Winnipeg needs to make short- and long-term plans to load up around him. Behind Morrissey, Dylan Samberg adds another layer of shutdown play. His emergence over the last couple of years, and Dylan DeMelo's consistency, have really solidified Winnipeg's top four. The Jets' most glaring need is a franchise forward to lead the way. Some teams can make up for that with elite depth. In Winnipeg, it's forced players to punch above their weight, which clearly brought the team down as a whole this past season. The problem is, Winnipeg has nothing close to a franchise forward in its pipeline. Scheifele met the minimum criteria in 2025-26 with a 103-point performance at 32, but the model dings the Canadian center for his age going forward. That's why the scoring forward role is more fitting at this point in his career; there just isn't a succession plan behind him, or another top-six center to add some balance up front. A true franchise forward at the top wouldn't just help Scheifele -- it would take some pressure off Connor, and likely help kick his game up a notch as well. Perfetti doesn't appear to have high enough of a ceiling to jump up to that, either. His comps after this season included Alex Kerfoot, Josh Bailey and Kris Versteeg. Maybe he can outpace that and become a part of the support core, but that's likely the limit there. None of Brad Lambert, Isak Rosén, or Brayden Yager is capable of vaulting past Scheifele or Connor to claim the role, either, so the internal option is either Scheifele channeling his idol Tom Brady in defiance of Father Time ... or nobody. So now it's up to management to trade for someone high end or be bold with an offer sheet. The outlook is similarly bleak for the "shutdown forward" category. Lowry fell short of meeting the criteria even when he was at his best in 2024-25, because it requires a higher-end, two-way driver with scoring included. There's no Mark Stone, Marion Hossa or Sam Reinhart on the roster or in the pipeline; Yager's biggest advocates believe he can become a capable second-line center, not Patrice Bergeron. Neal Pionk is the Jets' best bet at a scoring defenseman, but it would take a substantial bounce-back on his part -- and a substantial fix to the Jets' second line. No one drives a Cup-contending offense with outlet passes to Gustav Nyquist or Tanner Pearson. If Pionk can't shake it, management's going to have to get creative here, too. The free agent class is incredibly thin, so the team needs to swing big with a trade or try to promote from within. The best-case version of Elias Salomonsson could fill this role in the future, but that requires good health and two steps forward. Salomonsson's trajectory is likely to be closer to Samberg's, giving Winnipeg a shutdown defenseman with more puck skill than the Jets' next great power-play defenseman. On that front, Sascha Boumedienne and Alfons Freij represent long-term hope but nothing near short-term certainty. A depth forward? Winnipeg can probably acquire that. But that's small peanuts right now, considering the Jets' pressing needs at the top of the lineup. Can Winnipeg defy expectations, wedging open a window that looks slammed shut? The Jets want to win, now, despite their failure to make the playoffs. They're under more public pressure to win soon because Hellebuyck has gone public with the idea that Winnipeg can't afford to ice the status quo again next season. The pressure isn't solely external: Winnipeg's best players are aging out of their prime. Hellebuyck and Scheifele will each be 33 when next season starts. Morrissey is 31; Connor turns 30 in December. The only path from bubble team to legitimate Stanley Cup contender requires making major upgrades at a faster rate than the stars' decline. But we've explored targets up front and on defense, even discussing wildly unlikely offer sheets. It's possible to find a route back to the playoffs; finding two more elite forwards and one more elite defenseman appears to be out of reach. When Hellebuyck, Scheifele, Morrissey and Connor were younger, they were the next wave of elite talent on a team led by Blake Wheeler and Dustin Byfuglien in their prime. They were supplemented by other top youth like Patrik Laine, Nikolaj Ehlers and Jacob Trouba. And even though Wheeler and Paul Maurice were fond of describing those Jets as a young team, sometimes describing the team's failure to make a dent in the 2018 Western Conference final as an issue of inexperience, Winnipeg's young talent was a disproportionate part of its success. It is not a coincidence that the best playoff team in Jets history was its most cap-efficient: Winnipeg's youth was a feature, not a bug, with players on first and second contracts delivering extraordinary value relative to their cap hits. Fast-forward to today, with Scheifele's age dragging him down from meeting the minimum threshold for franchise forward to missing it entirely. There is no second wave. Perfetti, Salomonsson, Lambert, Yager and the No. 8 pick in this summer's draft are not what Connor, Scheifele, Laine, Ehlers, Morrissey, Trouba and Jack Roslovic were in 2018. How does Kevin Cheveldayoff pull off the impossible? Where is the top-end talent that pushes Winnipeg's quality core pieces into Cup contender territory meant to come from? Or is any reference to the Cup or winning "now" an issue of semantics, with a roster built to qualify for the playoffs but not to compete with the rest of the Central Division? Good is within Winnipeg's reach. Don't undersell the quality of its core. But greatness would take a spectacular offseason beyond the scope of today's imagination.