What Moves Can the Jets Make to Go From First-Round Exits, to Stanley Cup Champions?

The Toronto Maple Leafs have come to a crossroads, but there’s another Canadian team that, like the Leafs, have been a solid regular-season squad that just can’t get the job done in the Stanley Cup playoffs. And their name is the Winnipeg Jets. For the past six years, the Jets have failed to win a single second-round post-season game, and for the second straight season, they’ve won just one first-round game before getting knocked out in five games. So, what’s the fallout going to be in Winnipeg?

It’s a cloudy picture at best. For starters, star goalie Connor Hellebuyck isn’t going anywhere. He just signed a seven-year, $59.5-million contract extension that kicks in next season. Hellebuyck did not have a stellar playoffs, posting a 5.23 goals-against average and .870 save percentage, and his new deal has a full no-trade clause for the first three years. Teams would be lining up to take him off Winnipeg’s hands, but that’s just not happening.

Similarly, star center Mark Scheifele signed an extension identical to Hellebuyck’s. Scheifele has made a commitment to the Jets – and he probably would’ve received an even better deal if he hit the open market as a UFA – so he’s almost certainly going to be back in Winnipeg next season. But might it be time to investigate what veteran winger Nik Ehlers could bring back in a trade? The 28-year-old failed to score in the 2024 playoffs, and he’s heading into the final season of his contract. This isn’t to suggest Ehlers is a bad player, but something has to give, and there’s a case to be made that his salary cap hit of $6 million could be better spent elsewhere. Would Leafs winger Tyler Bertuzzi be a better fit in the top-six group of forwards? He’d bring more grit and spunk than Ehlers offers, and he’d be in that same cap-hit range.

After that, things get less clear. To be sure, the Jets have foundational pieces on the back end – most notably, defensemen Josh Morrissey and Neal Pionk – and up front, youngsters Cole Perfetti and Gabe Villardi are likely to stick around alongside veterans Kyle Connor, Adam Lowry and Nino Niederreiter. There’s a foundation that Jets GM Kevin Cheveldayoff will double down on, but intriguingly, there are a slew of soon-to-be-UFAs that Winnipeg could move on from.

For example, forwards Sean Monahan and Tyler Toffoli were helpful hands this season, but both of them had relatively tiny cap hits. Does Cheveldayoff break the bank to try and bring them both back, or spend that cap space to give the forwards a different look? And on defense, veterans Colin Miller, Dylan DeMelo and Brenden Dillon are all UFAs this summer. Maybe one or two of them come back to Winnipeg, but what about spending more cap space to bring in, say, Hurricanes D-man Brett Pesce? To be clear, Pesce will be one of the most pursued blueliners on the UFA market, but if Cheveldayoff can convince him he’s part of a flourishing group of defensemen, and the money is as good as it would be anywhere else, there’s a chance Pesce could come to Winnipeg.

Of course, the first big change is the retirement of coach Rick Bowness. Whoever replaces Bowness will have an impact on the roster, which is why Jets fans should expect a hiring behind the bench before free agency begins. What doesn’t seem palatable is running it back with the same group that simply cannot convert regular-season success into post-season glory, even with the incoming coaching hire on the horizon.

The Jets aren’t the only team facing this kind of problem, but Winnipeg fans have seen enough of the current group to know it’s time for significant roster alterations. Now it’s about chemistry, all-around depth and producing at the right time of the season. Returning the same lineup and expecting better results is not ideal, and for that reason, the winds of change are a-blowin' in Winnipeg.