If I were Kevin Cheveldayoff... (Part 1: Needs)

How best to maximize the Winnipeg Jets' chances at the Stanley Cup

I had been going along with my usual beginning-of-the-offseason series when I read Prashanth Iyer’s “If I were Steve Yzerman…” piece and decided to slightly shift my approach.

Like Prashanth, I’m going to try and give as accurate a picture as possible of the Winnipeg Jets’ contention window, and suggest how best to maximize their chances of winning within that window.

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The series thus far

1. Winnipeg Jets 2024-25 Season and Playoffs Review
   In our first post, we reviewed the Jets’ performance as a team in both the regular season and playoffs. We looked at team-level results and the general performance of the roster and its components.

2. The case for and against Winnipeg Jets extending Nikolaj Ehlers
   In our second post, we took a deep dive into Nikolaj Ehlers—Kevin Cheveldayoff’s biggest offseason question.

3. Should the Winnipeg Jets actually sign Jonathan Toews
   We then pivoted in our third post, covering some trending news: the idea of signing Jonathan Toews for the 2025–26 season, and what that might realistically look like.

4. Which Winnipeg Jets’ free agents are worth keeping
   I took a look at the value the Jets received from their free agents, how they project to perform, and made some suggestions on whether or not they’re worth keeping based on their impact.

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A quick disclaimer and a stats speed run primer

Like Prashanth, I want to disclaim that some of this is simply guesswork — which means there's always the chance of being wrong. It’s educated guesswork — using years of practice and expertise, some of the best models, research, and evidence — but guesswork nonetheless.

These are also not predictions. I don’t really care too much about “will the team” do something, as there are plenty of experts offering that type of analysis. It’s not my strongest area. My focus is on the should, given the best information available.

I will use data analysis with models and statistics supported by my own expertise, informed by what I’ve gleaned from video and microstats, and yes, filtered through my own human biases.

I’ll focus more on predictive value models and statistics, rather than descriptive ones, whenever possible.

There are many reasons for this, but the main one is that we’re talking about what Kevin Cheveldayoff and Scott Arniel should do — regardless of what they did or will do.

Descriptive models like Game Score, GAR, xGAR, WAR, and Net Rating tell you what a player did, given the environment they were in. Predictive models like Synthetic Goals (sG) tell you what a player would do if all players were on a level playing field.

For this reason, I’ll mostly use HockeyViz’s sG model or a weighted blend of Evolving-Hockey’s GAR and xGAR models for this series.

What is Winnipeg’s contention window

Connor Hellebuyck won the Hart Trophy, and for good reason. He was the clear-cut MVP for the best-performing regular season team in the NHL. His 51.4-goal performance beat the next-best goalie by 14.1 goals and the next-best skater — Leon Draisaitl — by 8.7 goals.

Another way to look at it: the value gap between Draisaitl and Hellebuyck was almost half the gap between Kyle Connor and Morgan Barron.

We’ll get into more nuanced contention window stuff, but the truth is that the Jets live and die by Hellebuyck. After all the analysis is done, the Jets are as competitive as Hellebuyck continues to be Hellebuyck.

That said, it does show that the Jets’ core value comes from older skaters like Hellebuyck, Scheifele, Connor, Ehlers, and Morrissey — with strong support from pieces like Iafallo and Lowry. There are some up-and-comers like Vilardi and Samberg, but the bus is still being driven by players who are likely, but not guaranteed, to be past their performance peaks.

The Jets are not a young team by any means — and especially not a young team when it comes to their highest-impact players.

If you look at aggregate performance stats focused on descriptive value — like The Athletic’s Net Rating or most WAR/GAR/xGAR models — the average peak performance age for skaters is 25–27. Once you adjust for coaching lag using more predictive models like HockeyViz’s sG, that peak moves a bit earlier to 24–26.

In short: models like Net Rating, Game Score, and WAR are influenced by coaching decisions. Coaches tend to be directionally right but often lag behind true performance. A young player has to prove they can take on a bigger role, while an older player has to prove they can’t.

This means most Jets are at an age where they’re more likely to get worse rather than better.

The Jets became a good team with this core in 2022–23, and a competitive team in 2024–25. Most team contention windows are four to six years, which gives Winnipeg about two to four years remaining.

They’re in the early middle of their contention window. The time to be aggressive is now.

First, projecting Jonathan Toews

We already wrote a bit about Toews last month here:

But now that he’s committed to Winnipeg, let’s take some shots at what value the Jets might get from him.

Toews was once a very good forward. At his peak, arguably the best in the NHL. But that peak faded well before his health issues in his final season. He’s also been out of the NHL for two years — and hasn’t played hockey at all during that time.

That’s not a normal situation, so there’s no normal way to predict what his return will look like.

Method 1: Weighted Average of His Last Three Seasons

Here, we weight his final season most heavily and go backward. That gives us a player with a positive offensive impact at even strength and on the power play, but negative elsewhere — working out to a 0.88 weighted GAR, or about a 32% forward.

That’s the impact of a slightly above-average 4C, though he’d be playing 2C minutes.

Method 2: Strict Average of His Last Three Seasons

One could argue that weighting the final season more heavily is unfair given his health issues. On the other hand, we’re not accounting for expected age decline, the risk he’s still not fully healthy (since full respiratory recovery from Long COVID is rare), or the impact of two years off — but fair enough.

Using a strict average, his value looks better. His offensive impact remains, and his short-handed and penalty differential metrics are slightly less negative.

This yields a 2.1 GAR, or about 40% — equivalent to a below-average 3C.

Method 3: Comparing Cohorts

To remove the health-season bias, I looked at all skaters who played at least 3,000 minutes between their age-30 and age-33 seasons.

I grouped them by performance level and looked at how many still played at 37 — and how they performed if they did:

The results aren’t all that surprising. The players who were the best between ages 30 and 31 were the most likely to still be playing at 37. These are mostly your elite players. That said, even those players saw significant declines.

First Line Forwards

Twenty-three of them were still playing at 37. Fourteen still provided top-six results. Two gave third-line impact. The remainder were essentially replacement-level forwards.

A reminder: this is all aggregate value, so a player who was third-line caliber talent but got first-line minutes likely shows up as second-line impact overall.

Second Line Forwards

This is the group where Toews falls — although he’s a bit below average for this cohort.

Interestingly, this group had the worst survivorship of the bunch.

Out of 53 skaters, only Corey Perry provided top-six results in his age-37 season. Zach Parise, Jeff Halpern, and Dominic Moore ended up providing third-line impact.

The rest were just fourth liners or depth-caliber forwards.

Third Line Forwards

Matt Cullen was a forward well known for his longevity. He remained in the NHL while still contributing positively to his team. Meanwhile, Jeff Carter and Chris Neil probably would have been better served retiring — like the rest of the sample.

Fourth Line (or Depth) Forwards

Jason Chimera finished at replacement level, while Craig Adams was below that.

The final forward in this group was Matt Hendricks — who, of course, was traded to the Winnipeg Jets to provide leadership and depth during the 2018–19 season.

…So, yeah.

Maybe Toews pulls a Corey Perry — managing to remain a top-six contributor at 37 despite not being an elite performer from ages 30 to 33. But more realistically, you’re probably looking at a decent bottom-six piece, if Toews is still even an NHL-caliber skater.

What they got

No criticism to Prashanth’s great work here, but I’m not a fan of using “Stanley Cup Winners’ Checklists.” It classifies individuals into tight archetypes when winning team rosters actually have a very large array of diversity in the performance of players in different roles.

To put it succinctly: it wrongly suggests you need specific pieces in specific roles to win — when many Cup-winning teams lacked quality players in those “required” roles. What really matters is the weighted aggregate value of all the pieces and how they combine.

Looking at the Jets’ roster based on last year’s performance*, it looks something like this:

*Toews’ value is a projection using the weighted average of his last three NHL seasons, but look earlier for other potential results.

The Jets’ top line produced the bulk of their forward value — thanks in large part to good health (Connor and Scheifele both played 82 games), high minutes (they ranked 5th and 6th in forward ice time), an elite power play (Vilardi and Scheifele ranked 7th and 27th in PP offense, respectively), and contributions in other non-5v5 situations.

Morrissey and Samberg are about as good as you could get for a one-two punch on the left side. And Connor Hellebuyck is the reigning NHL MVP for a reason.

After that? A whole lot of “mid” and subpar.

Potentially losing Nikolaj Ehlers puts a major hole in Winnipeg’s middle-six. Without their best performing forward (on a per-minute basis), the Jets project as a pretty average NHL team in the middle of the lineup.

And average gets you into the playoffs — not into the Finals.

Relatedly, I’m concerned that the top line’s performance could take a significant step back without Ehlers’ chaotic dynamism and puck recovery on the power play.

Also, without another strong middle-six performer like Ehlers, it increases the potential downside of Toews not magically bouncing back to top-six form from five years ago. If Toews isn’t good enough to carry a top-six line — which is very likely — the team will need a very strong winger to help prop up one of Namestnikov or Toews alongside Perfetti.

The other two largest issues fall on the blue line: the anchor that is their third left-shot defender, and the overall lack of quality on the right side.

Logan Stanley is one of the worst-performing NHL skaters. Don’t get me wrong — you can win with bad players. The Dallas Stars eliminated the Jets while dressing two similar anchors in Cody Ceci and Ilya Lyubushkin.

Still, Stanley is one of the worst negative contributors in the league — due in large part to a terrible penalty differential and an inability to contain faster forwards.

The right side not only lacks a legitimate top-pairing threat, but also is likely to regress this season:

• Dylan DeMelo, once a very strong and underrated defender, seems to be in age-related decline. He’d probably be best used in a mentorship and penalty-killing role on the third pair.

• Neal Pionk benefited from some extremely unsustainable team shooting on the second-unit power play and still struggles at even strength the second he’s not playing with Samberg.

• Luke Schenn has hovered around replacement level for most of his career and still somehow gets played.

• Colin Miller likely sees even less ice time with Schenn in the way.

If I were Kevin Cheveldayoff…

I’d be looking to maximize the Jets’ chances during the remainder of their 2-to-4-year contention window by:

• Adding a legitimate top-six scoring winger and/or centre

• Moving out cap deadweight and performance anchors like Stanley and Schenn

• Adding a legitimate top-four, right-shot defender

And those two additions — forward and defense — almost certainly have to come from outside the organization. We’ll take a deeper dive into Winnipeg’s prospect cupboards in our next post, but it’s becoming increasingly rare for even very good prospects to make an immediate NHL impact.

Next time we reconvene, we’ll dig into junior and the minors to see if any internal solutions exist. We’ll also scour free agency to identify any undervalued targets available to Winnipeg.