On May 2, many fans woke up to the news that Winnipeg Jets general manager Kevin Cheveldayoff had received a three-year contract extension. Reading that headline shocked my system before my morning coffee could. I was annoyed, to say the least.
Considering the Jets missed the playoffs, their locker-room chemistry has appeared to go sour and it seems that @Mark Scheifele wants out of Winnipeg, extending Cheveldayoff was an interesting decision.
That being said, some things stood out to me during Cheveldayoff’s year-end press conference. In about 30 minutes, I went from thinking keeping Cheveldayoff was a fool’s errand to believing that True North had extended someone that truly deserves his new deal.
“Over the course of time, I think we’ve built an origination that has tried to compete for the Stanley Cup over the last couple of years. There’s still work to do here to move forward,” Cheveldayoff said. “I’m very fortunate to have this opportunity and the confidence from ownership to move forward.”
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Later on, Cheveldayoff was asked about how his players referred to this season as embarrassing and a wasted opportunity.
“Certainly when you put the roster together and you’re the person in the organization that makes a great deal of decisions it weighs on you immensely,” Cheveldayoff explained. “I think we’re going through a process right now in the dressing room with the players. The exit meetings are extremely important in this environment and in this situation to ask those questions.
“I think equally as the team is disappointed the euphoria at the start of the season is very high this group had a lot of expectations in itself with some of the moves we made in the summer there was a tremendous amount of excitement. That level of highs is met with an equal amount of low when the team isn’t in the playoffs.”
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In person, Cheveldayoff didn’t place any blame on the coaches, the players or COVID-19. He just owned it and knows he needs to start digging through all the emotions of his players to find the issues within his group. The team is riding a deep low and emotions are all over the place. Right now, it seems like Cheveldayoff is going to run with that knowledge and won’t make any knee-jerk reactions.
Since becoming the Jets’ GM, Cheveldayoff has taken the Jets from being one of the worst teams in the NHL to being cup contenders in 2018. In 2019-20, most of the defensive core was either traded or had moved on from the team. This left Winnipeg’s back-end desperately exposed. Just two years later, their defence was restocked and positioned well heading into the 2021-22 season. Or at least, that was the case on paper.
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The way I see it, Cheveldayoff did what he could with the hand he was dealt. It didn’t translate into success this season for several reasons. Nevertheless, he did almost everything possible to rebound on the fly after unexpectedly losing a key defender like @Dustin Byfuglien.
This off-season would’ve been a terrible time to move on from Cheveldayoff. Winnipeg’s to-do list isn’t long but it features very important tasks. Not only would a new general manager have to bring in their own coaching staff, but they’d also have to re-sign @Pirre-Luc Dubois and others, along with potentially trading Scheifele and @Blake Wheeler.
Talk about throwing someone into the fire just when they step into the door.
If we’re truly being honest, Cheveldayoff has proven himself to be a worthwhile GM. From a development standpoint, 27 of their 58 draft picks between 2011-18 have played at least one NHL game. Aside from Wheeler’s five-year, $41.25-million contract, most of the contracts he’s handed out have aged fairly well.
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Besides the lack of legitimate long-term playoff success, Cheveldayoff goes into every season with the best parts he can find to win. He has high taxes and Manitoba’s harsh winters to compete against. Those factors can easily turn players off from wanting to come to Winnipeg.
Do you think Cheveldayoff should’ve been extended? Or was his time up a while ago?

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