![\"Kevin](\"https:\/\/www.rawchili.com\/nhl\/wp-content\/uploads\/2026\/03\/Kevin-Cheveldayoff-Jets-1200x800.jpg\")
Kevin Cheveldayoff, general manager of the Winnipeg Jets (Photo by Jonathan Kozub\/NHLI via Getty Images)<\/p>\nIs it time for the Winnipeg Jets organization to move on from the only general manager (GM) they\u2019ve ever known?<\/p>\n
As we begin to sift through the rubble of the Jets\u2019 disastrous 2025-26 season that ended with a thud Thursday, the question of whether Kevin Cheveldayoff has reached his expiration date is one that must be seriously asked.<\/p>\n
Cheveldayoff\u2019s Long & Mixed Tenure As Jets GM<\/p>\n
In a hired-to-be-fired business such as hockey front-office management, holding a GM title for 15 years might as well be an eternity, but that\u2019s exactly what Cheveldayoff has done. He is the longest-tenured GM other than St. Louis Blues GM Doug Armstrong, who is stepping down on July 1.<\/p>\n
The now-56-year old Cheveldayoff has been the main architect of every draft pick, signing, and trade from Day 1 of the Jets\u2019 relocating from Atlanta in 2011 through the decade and a half that\u2019s followed to now.<\/p>\n
Kevin Cheveldayoff, general manager of the Winnipeg Jets (Photo by Jonathan Kozub\/NHLI via Getty Images)<\/p>\n
Like any GM, he\u2019s had successes and failures. Among his successes, he drafted Mark Scheifele, Adam Lowry, Jacob Trouba, Connor Hellebuyck, Nikolaj Ehlers, Josh Morrissey, Kyle Connor, and Dylan Samberg and oversaw their development into key pieces of either their current or past core. He\u2019s also made some shrewd deals, such as the one with the Los Angeles Kings for Alex Iafallo and Gabriel Vilardi in 2024 and the one with the St. Louis Blues for Paul Stastny in 2018.<\/p>\n
Despite being GM of an undesirable market compared to many others, he convinced most of his drafted players, and others he acquired through trades, to sign long-term extensions and even become Jets for life. He does deserve credit for getting a lot of great talents \u2014 who could have gone elsewhere for the same or even more money \u2014 to buy into what he has been selling.<\/p>\n
It hasn\u2019t been all sunshine and roses. His draft choices over the past 10 years have produced more busts than high-impact players, he let Ehlers get away last summer for nothing<\/a>, and he dished out big contracts to players like Nate Schmidt and Blake Wheeler that aged like milk and ultimately needed to be bought out.<\/p>\n Jets Haven\u2019t Had Much Playoff Success Over 15 Years<\/p>\n At the end of the day, professional sports is a results-oriented business. The results over 15 years have been good in the regular season but subpar in the playoffs.<\/p>\n The Jets own a 545-404-99 all-time regular-season record under Cheveldayoff and they\u2019ve made eight playoff appearances, but have only won four rounds and have been eliminated in the first round five times.<\/p>\n Two of the four round wins came when the Jets advanced to the Western Conference Final<\/a> in 2018, which seems like a deep run but really saw them capture only nine of the 16 wins required to hoist the Stanley Cup and was almost a decade ago now.<\/p>\n One has to ask as to whether after 15 seasons at the helm, Cheveldayoff is capable of elevating the team above \u201cbridesmaid\u201d status.<\/p>\n Cheveldayoff Deserves Brunt of Blame for 2025-26\u2019s Regression<\/p>\n Professional sports is also a what-have-you-done-for-me-lately business, and what Cheveldayoff has done lately has not been good at all. His decisions and free-agent additions coming out of the team\u2019s Presidents\u2019 Trophy-winning 2024-25 were nothing short of disastrous and were the biggest factor for the Jets\u2019 regression from 56 wins last season to just 35 this season. <\/p>\n As mentioned, he lost the speedy and dynamic Ehlers in free agency and signed only over-the-hill veterans who made the team dreadfully slow and unable to keep up with up-and-coming young squads.<\/p>\n The Jets suffered through a franchise-long 11-game losing streak and were dead last in the NHL<\/a> by early January as a result of their lack of speed, sharp drop in secondary scoring, lack of defensive structure, and worse goaltending. While hung around in the Western Conference wild-card race for a while after the Winter Olympic break, they were mathematically eliminated on April 13<\/a> and joined a small and dubious club of squads that failed to even make the playoffs the season directly after being best in the league. Of those five clubs, the Jets\u2019 points decline of 34 is greatest of all.<\/p>\n Other Teams in Similar Position Going In New Directions<\/p>\n Cheveldayoff is not a terrible GM nor has he ever been out of his depth. He took over a team that came from Atlanta with completely bare cupboards and helped them become usually respectable and occasionally dominant. However, even smart people\u2019s views grow stale over time and having the same leader for too long can prevent an organization from evolving and growing.<\/p>\n Teams in similar situations to the Jets \u2014 namely, ones that made the playoffs last season but missed this season \u2014 have already sent their GMs packing. The Toronto Maple Leafs fired GM Brad Treliving<\/a> on March 30, while the New Jersey Devils fired GM Tom Fitzgerald<\/a> on April 6. These teams have recognized that the status quo wasn\u2019t working and that they needed to bring in someone with new ideas and a new philosophy.<\/p>\n Other teams have parted with their GMs and then won the Stanley Cup soon after in recent history, including the Chicago Blackhawks (hired new GM Stan Bowman in 2009 and won in 2010, 2013, and 2015) the Washington Capitals (hired new GM Brian MacLellan in 2014 and won in 2018), and the Florida Panthers (hired new GM Bill Zito in 2020 and won in 2024 and 2025).<\/p>\n True North Sports & Entertainment, which owns the Jets, finds itself in a similar spot with a key offseason ahead. The team is either going to be able to make the moves necessary to get back to competitiveness next season, or not be able to make those moves and be destined to spend the next few-to-several seasons in the mushy middle or worse.<\/p>\n True North has to decide whether Cheveldayoff is still the right man for the most-important role in the organization and if they can still trust his leadership and thought process. They should factor in his decisions over the past year and whole body of work when making that decision.<\/p>\n True North is extremely loyal to their people, but they need to ask themselves if keeping him would be an example of being loyal to their own detriment.<\/p>\n Free Newsletter<\/p>\n \n Get Winnipeg Jets coverage delivered to your inbox <\/p>\n In-depth analysis, breaking news, and insider takes – free.<\/p>\n![\"Winnipeg](\"https:\/\/www.rawchili.com\/nhl\/wp-content\/uploads\/2026\/04\/Winnipeg-Jets-Whiteout-1200x800.jpg\")
The Jets have made the playoffs eight times under Cheveldayoff, but won just four rounds. (Photo by Jonathan Kozub\/NHLI via Getty Images)<\/p>\n![\"Mark](\"https:\/\/www.rawchili.com\/nhl\/wp-content\/uploads\/2026\/03\/Mark-Scheifele-Jets-3-1200x800.jpg\")
The Jets are at a pivotal point in franchise history. (Terrence Lee-Imagn Images)<\/p>\n