​Buying into an organization that isn’t based in a marquee city like New York or Los Angeles, but rather a place built on a winning attitude and a constant drive to improve, was once one of the Detroit Red Wings’ greatest strengths. Now, the franchise finds itself somewhere it’s rarely been, stuck in a decade-long playoff drought, with the winning culture behind the Winged Wheel wearing thin enough that a cornerstone piece like Dylan Larkin has stopped trusting the process.What Detroit is chasing is something it used to be, a destination where the winning culture matched the appeal of an underrated city like Detroit, Hockeytown in every sense of the word. That kind of destination-building has played out recently just north of the border, with the Winnipeg Jets.Winnipeg Jets Respond To Connor Hellebuyck’s Trade Request Becoming PublicGeneral Manager Kevin Cheveldayoff addresses the star goaltender’s public demand for a change of scenery as the organization weighs high-stakes trade offers ahead of a looming training camp.Despite years as a legitimate Stanley Cup contender, the Jets still sit on plenty of players’ no-trade lists. So how did a market like that build itself into a Western Conference power, one that won the Presidents’ Trophy as the league’s best team during the 2024-25 season? A lot of it traces back to longtime general manager Kevin Cheveldayoff, who has steered the franchise since its relocation from Atlanta and built something that both the team and the city have earned.Bookmark The Hockey News Detroit Red Wings team site to stay connected to the latest news, game-day coverage, and player features.While free agents on the open market have often steered clear of Winnipeg, the Jets’ own core has stayed. Stars at nearly every position, Mark Scheifele and Kyle Connor up front, Josh Morrissey on the back end, and Connor Hellebuyck in net, have all signed long-term deals and bought into the organization, something that would have seemed unlikely for a franchise with little track record of sustained success before recent years.Winnipeg took a step back this past season due to some free-agent signings that didn’t pan out and rough injury luck, and it’s currently navigating its own controversy surrounding Hellebuyck’s future. But even that situation reflects the strength Cheveldayoff has built. Convincing Hellebuyck to sign long term in the first place, and now holding the leverage to trade him on Winnipeg’s terms if it comes to that, all while a three-time Vezina winner and Olympic gold medalist still has term left on his deal, is the kind of position most organizations would envy.In many ways, that’s exactly what Detroit has lost. The Red Wings could use Winnipeg’s handling of the Hellebuyck situation as something of a mirror for their own with Larkin. A player wanting out doesn’t have to mean blowing up everything an organization is building, and that appears to be the mentality guiding Winnipeg as it continues to look like no