How good at his job is Winnipeg Jets’ GM Kevin Cheveldayoff?

The 2023 NHL Trade Deadline has come and gone. The Winnipeg Jets splashed around the edges of the pool, and made the following transactions:

Yikes. For those desperately pleading for the Jets to push all-in this year given their sheer volume of 2024 UFA’s, this is a disappointment. A big one. All of that is covered here.

Let’s turn our attention to the man at the helm of this veering ship, Winnipeg Jets General Manager Kevin Cheveldayoff.

Cheveldayoff is the third-longest-tenured General Manager in the NHL having joined the team back in September of 2011, putting him behind only Doug Armstrong (St. Louis) and David Poile (Nashville) in tenure.  He has been the only GM of the franchise since it relocated from Atlanta. Put frankly, Chevy is enjoying job security envied by most college professors.

In that time, the Jets regular season record has been a pedestrian 456-348-88. The team has made the playoffs 5 of 11 eligible seasons, the apex culminating in a trip to the Conference Finals in 2018. Decent? Sure. Celebration worthy? Absolutely not.

This begs the question, how good is Kevin Cheveldayoff at his job? Let’s look at 2 factors germane to the GM role: (1) the Draft; and (2) Trades.

How have the Winnipeg Jets drafted under Kevin Cheveldayoff?

A common refrain is that the Winnipeg Jets draft well. The steady drumbeat from the organization is the proliferation of the ‘draft and develop’ model. It goes: draft deftly, and then develop that talent to its maximum potential. But is it true? Has Chevy put this model into practice? Let us look at Winnipeg Jets draft picks by year, with a heavy focus on first-round picks.

2011

The first-ever Jets 2.0 draft pick was none other than Mark Scheifele with the 7th overall selection. Mark has been a productive player – behind only Kucherov, Huberdeau and Gaudreau in scoring from the 2011 vintage (Kucherov and Gaudreau were steals much later in the draft). Chevy also drafted Adam Lowry in the 3rd round who has become a foundational piece for the Jets and even hired his Dad. So far, so good (except for the Dad part).

2012

Trouba entered the league with great anticipation as the Jets’ 9th overall pick, and while he had some good seasons with the Jets, there was always an undercurrent of disappointment in failing to reach those lofty expectations. He’s transformed his game in New York as more of a Brad Marchand ‘agitator-sandpaper’ type (without any of the personality). That said, the talent pool in 2012 was sparse, so this was a decent pick.

The real coup d’état of this draft was selecting Connor Hellebuyck in the 5th round. One Vezina trophy and dozens of single-handed wins later, Connor was a tremendous pick.

2013

Josh Morrisey was taken 13th overall. While it looked dire for a few seasons, he has since blossomed into one of the best defensemen in the league. The two defensemen selected after Morrissey (Pulock and Zadrov) have had solid, but unspectacular careers, so this pick was an excellent one. He’s unlikely to win the Norris this year, but he has my vote.

Nabbing Andrew Copp in the 4th round was also savvy, even if his exit was a bit unceremonious.

2014

You can’t teach speed. Nikolaj Ehlers was taken 9th overall in 2014, and while we haven’t yet deployed him properly, he is arguably our best forward. Biases aside, Dylan Larkin went 15th overall and David Pastrnak fell to the 25th pick. Objectively, Ehlers has failed to perform at their levels, but both Paul Maurice and Rick Bowness have bungled his deployment significantly.

2015

Kyle Connor and Jack Roslovic were taken in the first round. Much like the chicken, KFC has been finger-lickin’ good. Fresh off a Lady Byng win, Connor is one of the NHL’s premier scorers, although his attention to defense is heart-attack-inducing – again, much like the chicken.

Roslovic has blossomed somewhat in Columbus, but never really did much in Winnipeg. The Jets could have used that pick to select Sebastian Aho, but whiffed.

2016

Patrick Laine went 2nd overall to the Jets and proceeded to tear up the league. The pick was somewhat of a no-brainer, and he immediately became a fan favorite. Soon-to-be ex-Jet Logan Stanley was also selected in the 1st round of this draft, so we have to balance the good with the bad. Laine’s trade muddies the waters a bit, but regardless, he was a good – if not obvious pick.

2017

The Winnipeg Jets used their 1st and 2nd round picks to select Kristian Vesalainen and Dylan Samberg respectively. That is a huge gutter ball on Vesalainen, but Samberg has played very well this year and should be a larger part of the Jets’ future moving forward (but likely won’t be).

2018

The Jets didn’t have a first-round pick in 2018 having traded it for Paul Stastny for the 2018 playoff push. David Gustafsson (2nd) and Declan Chisholm (4th) are the standouts from this draft year, but all told a very forgettable draft year.

2019-2022

The results here are inconclusive. Evaluating drafts in hindsight can be tricky at the best of times, so let’s give these kids some time to develop. Cole Perfetti has shown promise, and Ville Heinola has flashed (but again, has not been given the opportunity to prove himself).

Verdict: The Jets have drafted pretty well all things considered, and Chevy deserves credit for that. The inability to rebuild the defensive core through the draft is concerning and misses on Rosolvic, Stanley and Vesallainen hurt, but drafting is not an exact science.

How has the Winnipeg Jets trade market fared under Chevy?

How about trades? Any Faustian bargains out there? I’ve ranked the notable trades Chevy has made since 2011 from best to worst transactions:

1. February 26, 2018  – Paul Stastny FOR 2018 1st and 2020 4th round picks:

Everyone loves Pauly Walnuts, and this led to an on-again, off-again bromance between him and the Winnipeg Jets. It also solidified the roster for a deep run in the 2018 playoffs.

2. February 18, 2020 – Dylan DeMelo FOR 2020 3rd-round pick

While most likely not a true first-line defenseman, DeMelo has been well worth this price and arguably one of the Jets’ best D-Men (which is not great).

3. June 30, 2013 – Michael Frolik FOR 2013 3rd and 5th Round Picks:

Michael Frolik was a good addition and became a very nice depth piece. Much like the DeMelo trade -not earth-shattering, but solid.

4. June 17, 2019 – Jacob Trouba FOR Neil Pionk and a 2019 1st-round pick

That’s it for the good ones. Every other Chevy trade is suspect in some way (outside of Copp), including this one. A year ago, this was a slam dunk Net positive, but given Pionk’s recent play, it is hard not to believe we couldn’t have garnered more.

5. I’ve talked about the Patrik Laine trade before, so no need to bring up painful memories.

In short, if PLD doesn’t sign long-term in Winnipeg – this was a bust.

6.  February 11, 2015 – Evander Kane, Zach Bogosian, Jason Kasdorf FOR Brendan Lemieux, Joel Armia, Drew Stafford, Tyler Myers and a 2015 1st-round pick

It’s ironic that Kane’s terrible behavior necessitated this trade and yet he is the only player with any real consequence from the swap meet.

Verdict: This year’s complete draft paralysis, combined with the Dillon and Schmidt trades veer Chevy’s trading record into the ‘below average’ category. Most of the action was borne out of necessity, or for a playoff push, but overall lackluster long-term success here.

BONUS: A real sore spot rests with the Winnipeg Jets’ activity (or lack thereof) in free agency. Matthieu Perreault is the one bright spot amidst a rotating dumpster fire of luminaries that include Matt Hendricks, Derek Forbort, and Adam Brooks. These signings are a zero-sum proposition as they fill roles typically used for young players – antithetical to the ‘draft and develop’ model. As such, Chevy takes an “L” with respect to free agency.

In all, Chevy has been a good drafter, below-average in trades, and terrible in free agency. Other pain points include:

• The handling of the Kyle Beach scandal (terrible by any metric).
• Keeping Paul Maurice around waaaay too long.
• Failure to replenish D core after Buff left.
• And, for good measure again, this 2023 Trade Deadline.

The reality is that Chevy isn’t going anywhere. He just signed a 3-year extension back in May, and all reports indicate that he and Mark Chipman are going to continue to Thelma and Louise this organization in perpetuity (hopefully not to the same end).

That doesn’t ease the sting of once again settling for mediocrity in 2023. How long will Jets fans settle for “Meh”? The man in charge for over a decade has ostensibly ended another season with yet another bumpy landing. When is enough, enough?