Kelly McCrimmon and Kevin Cheveldayoff have much in common.
They are Saskatchewan products whose hockey roots run deep around here, including junior careers riding buses up and down the Trans-Canada Highway with the Brandon Wheat Kings where they racked up more penalty minutes than points. Both came up short of playing in the NHL but eventually made it to the big leagues — first as assistant general managers, then, ultimately, in the big chair calling all the shots.
Each now has a Stanley Cup ring. Cheveldayoff in a supporting role with Chicago in 2011, and McCrimmon as lead in Las Vegas in 2023.
The similarities pretty much end there, especially if you are looking at how these two friends turned fierce hockey rivals now approach their current jobs. The differences are truly (K)night and day.
McCrimmon and company repeatedly rolled the dice in Sin City and quickly built a champion in a “win at all costs” environment that is as cold and calculated as the Mob. Here in Winnipeg. Cheveldayoff and his employer, True North, continue to take a slow and steady approach that appears to be spinning its wheels in a “just happy to be here” climate that operates, at times, like a Mom-And-Pop shop.
To be clear, there’s no specific tried-and-true way to build a hockey heavyweight. It’s hard not to notice the two very different paths McCrimmon and Cheveldayoff have taken and, most importantly, where they’ve led.
In the 12 years since the NHL returned and Cheveldayoff was given the reins, the Jets have made the playoffs five times. That happens to be the same amount of post-season appearances by the Golden Knights, who weren’t even a twinkle in the eye of commissioner Gary Bettman back in 2011. Winnipeg has won three playoff rounds. Vegas has won 11, including two against the Jets.
Roster construction is especially stark.
Sure, the Golden Knights found treasure in other teams’ trash during the expansion draft. Just six years later, Jonathan Marchessault, William Karlsson, Reilly Smith, Shea Theodore, Brayden McNabb and William Carrier are the only remaining “misfits” from the inaugural 2017-18 season. Not content with going all the way to the Stanley Cup Final in their expansion year and losing to the Washington Capitals, the scalpals came out in Vegas and major surgery was performed.
Holes were filled with the kind of efficiency we’d all love to see on our bumpy roads every spring in Winnipeg.
The organization made significant adds in the trade market, including Winnipegger Mark Stone, Jack Eichel, Adin Hill, Chandler Stephenson and Ivan Barbashev, and shrewd free-agent buys such as Alex Pietrangelo, Zach Whitecloud (of Sioux Valley Dakota Nation near Brandon) and Alec Martinez. They weren’t afraid to take big swings by moving out scores of draft picks, multiple young prospects (Nick Suzuki, Cody Glass, Peyton Krebs), numerous beloved players (Marc-Andre Fleury, Max Pacioretty, Alex Tuch, Ryan Reaves, Nate Schmidt, Paul Stastny) and even a couple coaches (Gerard Gallant, Pete DeBoer) all in the name of constantly trying to get better.
McCrimmon has also made it a clear priority to mine for talent in his own backyard, with five Manitobans (Stone, Whitecloud, Brett Howden of Oakbank and Winnipeg’s Keegan Kolesar and injured forward Nolan Patrick), and many other WHL alumni on the roster who appeared to be well-equipped for the rugged marathon of playoff hockey.
Now, the Golden Knights have reached the NHL summit in just six years and made many peers look foolish in the process. And while the take-no-prisoners approach clearly paid off, it also came with a steep price.
“Damn high,” McCrimmon told Sportsnet this week of the toll on a human level when it comes to relationships. “But at the same time, if you have these jobs and you want to avoid the hard decisions, you probably shouldn’t have these jobs.”
There haven’t been a ton of hard decisions in Winnipeg over the years. The majority of trades have been out of last-ditch necessity, with clearly disgruntled players such as Evander Kane, Jacob Trouba, Patrik Laine, Jack Roslovic and Andrew Copp eventually moved. The Jets haven’t dipped their toes very deep in free agent waters, opting to spend their salary-cap hit on homegrown products they’ve locked up with long-term extensions.
The waiver wire and bottom-six forwards and depth defencemen is about as adventurous as it usually gets when it comes to addressing needs.
Cheveldayoff subscribes to the “draft and develop” model, with the likes of Mark Scheifele, Adam Lowry, Connor Hellebuyck, Kyle Connor, Josh Morrissey, Nikolaj Ehlers, Mason Appleton, Dylan Samberg, David Gustafsson and Logan Stanley all on the roster this past year.
You know how many Vegas draft picks skated in the playoffs this year? One. Defenceman Nic Hague.
It would be one thing if that Jets’ long-term loyalty had been rewarded, but Winnipeg’s lack of sustained success speaks volumes. Running back mostly the same core, year after year, has produced the same middling results.
It even applies to the coaches, where only Claude Noel has truly been fired. Paul Maurice was kept well after his message went stale, but remained behind the bench until he finally pulled the plug on himself.
There’s no question it’s part of the organizational culture. Since Cheveldayoff was hired, every team except St. Louis and Seattle (who just joined the league in 2021) have changed their GM at least once. The Blues won the Stanley Cup in 2019, earning Doug Armstrong plenty of rope. (They, too, beat the Jets in the playoffs that year). The Kraken just went to the second round in their sophomore campaign and appear to have a bright future.
Winnipeg fans are clearly frustrated, with 1,300 empty seats on average for every game last year and a massive season-ticket drive now underway to try and claw back some of what’s been lost, despite no clear direction for the on-ice product going forward.
Players are frustrated, too. Scheifele and Hellebuyck are apparently seeking one-way tickets out of town. Pierre-Luc Dubois, who was the return for Laine and Roslovic, has also joined the “get me out of here” list.
A tangled web, indeed. The one silver lining, I suppose, is that major, long-overdue change is looming. Not by choice, of course. The approach taken by the organization over the next few weeks is going to be fascinating, while also charting the course for years to come.
Vegas has now proven you don’t need an endless runway to take flight, provided the right buttons are being pushed.
No doubt Cheveldayoff will be extending congratulations to his old buddy in the coming days. Perhaps, in the process, he can also ask McCrimmon for a few tips on pulling off the kind of ruthless, high-risk high-reward aggression that has become the modus operandi for a Vegas franchise where winning truly is everything.
What a refreshing change that would be, don’t you think?
Mike McIntyre grew up wanting to be a professional wrestler. But when that dream fizzled, he put all his brawn into becoming a professional writer.
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