If I were Kevin Cheveldayoff... (Part 2: Free Agency)

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

If I were Kevin Cheveldayoff… I’d simply sign the best players at a fraction of the market rate!

Well folks, thanks for reading The Five Hohl; see you next time.

In all seriousness, today is free agency so let’s take another look at what the Jets have, who they are, and what they need. And then let’s highight some of the free agents available and their potential fit on the Jets.

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The series thus far

1. Winnipeg Jets 2024-25 Season and Playoffs Review
   In our first post, I reviewed the Jets’ performance as a team in both the regular season and playoffs. I 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, I took a deep dive into Nikolaj Ehlers—Kevin Cheveldayoff’s biggest offseason question.

3. Should the Winnipeg Jets actually sign Jonathan Toews
   I 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.

5. If I were Kevin Cheveldayoff… (Part 1: Needs)
   I took stock of the team’s current strengths and weaknesses and began building a plan for maximizing Winnipeg’s contention window.

6. Who is Sascha Boumedienne and update on Jets prospect cupboards
   A deep dive on Sascha Boumedienne with an analytical look at the Manitoba Moose and the Winnipeg Jets’ prospect cupboards.

7. Draft day two and another update on Jets prospect cupboards
   A deep dive on Sascha Boumedienne with an analytical look at the Manitoba Moose and the Winnipeg Jets’ prospect cupboards.

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Quick Stats Primer

We’re focusing on “what I would do,” which means we’re not focusing on what the Winnipeg Jets have done.

This also means that we’ll focus on predictive metrics over descriptive metrics. We only care about what players have done provided it is a reasonable assumption that they will likely continue doing so.

Evolving-Hockey.com has two total value metrics: GAR and xGAR. Oversimplified…

GAR is a game score or box score stat. It takes all the things you’d see on a game sheet (goals, assists, blocks, hits, giveaways, takeaways, penalties, penalties drawn, goals for and against, shots for and against, etc.) to approximate the impact a player had on the games they played.

xGAR is more of a super advanced plus-minus, taking the expected goal differential (a shot +/- where shots are weighted relative to shot quality) a player has while on the ice. It is adjusted for many usage factors (linemates, line matching, etc.) and then adds goalie talent (i.e., Goalie GAR) and shooting/finishing talent.

These models are both explicitly and intentionally focused on descriptive value. They tell you how a player did in the context of their season. A predictive model is more about what we expect a player to do moving forward in any particular situation.

I have blended the individual aspects of GAR and xGAR (even strength offense, even strength defense, power play offense, short-handed defense, penalty drawing, and penalty taking) in a manner that increases the predictive value of these models.

That said, synthetic goals—sG from HockeyViz.com—is explicitly and intentionally focused on predictive value, and so it’s generally better at telling you how a player will play in the future. sG is quite complex, but it also uses math to isolate a player’s performance in key areas, like their influence on shot quantity, quality, finishing, setting, and ability to transition.

Got it? Good.

Reminder: Where we’re at and what questions we have

The Winnipeg Jets are still a good and flawed team. There are some real questions with the current roster:

• Will the top line have another strong year due to ideal health despite heavy minutes, or will they regress back to their norm as the power play returns to how it was before Nikolaj Ehlers added a dynamic element and puck retrievals?

• Will the gamble pay off with Jonathan Toews, who hasn’t performed like a strong top-six forward since the 2015–16 season, nearly a decade ago?

• How will Adam Lowry look when he returns from hip surgery? How will Lowry and Toews impact the Jets’ centre depth in the most important position in hockey (after maybe goaltending)?

• Will Nino Niederreiter bounce back? Will Alex Iafallo sink after the contract extension?

• Will the Jets be able to plug the VERY large hole created by Nikolaj Ehlers leaving?

Altogether, it becomes clear that the Jets need 1–2 more bona fide top-six talents on their roster to replace Nikolaj Ehlers, act as a contingency plan for Toews and/or Lowry, and counter any potential fallback from Kyle Connor, Mark Scheifele, Gabe Vilardi, and (to a lesser extent) Alex Iafallo.

If bona fide top-six talents are not available, the Jets may be forced to gamble on youth potential and/or bounce-back candidates. That said, when you increase risk with these gambles, you need more shots at success, so you’d want 3–4 candidates, including Toews.

The Jets’ backend has its own questions despite not having any real roster positions up for grabs:

• Will Neal Pionk’s value tank if the second power play unit’s shooting percentage falls back to earth this season or Dylan Samberg is unable to carry him defensively?

• Will Dylan DeMelo bounce back, or is this fall what we should expect moving forward?

• Will the Jets ship out some dead weight on the back end (Logan Stanley and Luke Schenn) to make room for the better skaters, or is their plan to simply risk Ville Heinola to waivers, only to see him go to Europe or Group 6 UFA this summer?

There’s not really any need to add in free agency, except maybe some waiver fodder to insulate the Manitoba Moose next season.

It’s more of a question of who they move or let go or lose.

Finally, with goaltending, there are three questions:

• How much of Connor Hellebuyck’s MVP season impact will he retain, and how much will he fall?

• How much will the Jets play Hellebuyck this season?

• And how well will Hellebuyck perform in the playoffs, which the Jets most likely will see once again barring any real upsets or poor luck?

Free Agent Targets: Wingers

The Jets need to add one to two legitimate NHL wingers. Ehlers is likely gone and may have been priced out, being arguably the best free agent to hit July 1st. Toews could be a surprise, but right now the Jets need some strong wingers to help elevate their lacklustre pivots.

Above are (almost) all (of) the (mostly) exclusive wingers available in free agency.

I’ll divide them into tiers.

Tier 1: Nikolaj Ehlers

Nikolaj Ehlers is one of the best-performing wingers in the modern NHL… once you adjust for the fact that the Jets never seem to play him unless forced to.

Sure, he’s top 10 since 2019 in 5v5 points and goal +/- relative to ice time. Sure, he’s the highest-scoring point-per-game player since 1999 at his ice time per game or less. Sure, whenever the team has been forced to play him on the top line or the top power play unit, both Ehlers, his linemates, and his teammates have done better.

But three coaches haven’t trusted him enough despite the nearly eight years of dominance when Ehlers has been on the ice.

That’s why Ehlers is likely looking elsewhere, despite him being exactly what this Jets roster needs most.

And with how shallow the talent pool is this year, he’s likely been priced outside of the Jets’ budget and potentially out what the Jets should pay anyways. However, banners do fly forever, and Ehlers should still be competitive for the 2-4 years remaining in Winnipegs competitive window.

Tier Two: Top-Six Performers

These are the three wingers to perform like top-six skaters over the past couple of seasons.

Andrew Mangiapane is an undersized winger, and the Jets may be hesitant as they seemingly put (too much) of a premium on size. He performs well at even strength, both offensively and defensively, and is pretty solid on special teams as well. His finishing disappeared during his last years in Calgary, which led him to playing in Washington for far fewer minutes, resulting in far fewer points.

He’s probably the best Ehlers replacement. He’s also a lot cheaper, coming in around $4M projected AAV from most sources.

If you can’t have Ehlers, why not have an old teammate in Jonathan Drouin? Drouin has had an interesting career. He was fairly mid in Tampa Bay, but being only average as a former 3rd-overall pick on a team pushing to win Stanley Cups meant he was shipped to Montreal, where he stunk. Drouin’s defensive game cratered with the Habs, but bounced back in Colorado. There’s risk in how much was him returning to form, being insulated by a strong team, or just a solid fit that worked out.

While his impact is projected as the same or slightly worse than Mangiapane given the same role, his projected cap hit is about $500K more due to his higher point totals.

Finally, we have James van Riemsdyk, a player who was often sought after by Jets fans on HFBoards back in his Philadelphia days. He’s 36, so he wouldn’t be reducing Winnipeg’s average age, and his ice time is decreasing as the years have built up, but he’s still useful and is much better than his projected cap hit of ~$1.5M.

Tier Three: Gambles

The next set of players aren’t exactly great bets for top-six impact strong enough to carry a line with Toews and Perfetti, but they have been useful previously on some teams in some situations.

Mason Appleton is not the answer, and one the Jets likely do not pursue at ~$3.5–4.0M AAV for three or so years.

Max Pacioretty had a rough year this season in Toronto, but ranged from useful to excellent forward in Washington, Carolina, Vegas, and Montreal. He also comes cheap, at around a projected $1M, and likely low risk with only a year to cost.

Jeff Skinner is all offense, no defense—which may be useful for a team like Winnipeg that does well defensively at 5v5, but offense has been its weakness both in the regular season as well as the playoffs. He probably costs $2.0–2.5M AAV, likely only for one year.

Evgenii Dadonov was a below–top-six caliber performer for the first time since Jets 2.0 entered the NHL. Sure, there’s risk he might be on his way down, and I’m not sure he wants to play in Winnipeg—just like many skaters on this list—but you could do worse at around $1.5M projected salary, likely for 1–2 years.

Anthony Beauvillier was a pretty solid forward for the New York Islanders. Once he left NY, he never really found a space to stay, and struggled in some cases. He’s played for six teams in three seasons. That may be bad luck, or it may be teams falling for the same bias, or it may be legit. There’s risk too, as Beauvillier probably earns term unlike the previous few options, and likely more costly at ~$2.5–3.0M AAV.

Tier Four: #$%* it, depth (or overrated)

Victor Olofsson and Connor Brown are intriguing depth players. Same with Adam Gaudette. However, I just put them here because I wanted to show why I’m hesitant on Brock Boeser as a free agent.

It sounds like he may get bid up to Ehlers-type levels, yet he hasn’t been in the same range as Ehlers for performance since the 2017–18 season. I hear he’s a nice guy, but Boeser’s only positive impacts have been his shot and power play.

Essentially, imagine if Kyle Connor was slow.

Free Agent Targets: Kinda Wingers, Kinda Not

I won’t break these into tiers like the last one, but some of these guys are ones that I would pursue if I were the Jets.

A competent centre who can also play wing like Pius Suter or Nick Bjugstad would give the Jets some extra options for their centre position if Toews struggles and while Lowry is on IR.

Jack Roslovic returning would be a neat story, and I know many Jets fans have wished for Mikael Granlund, Gustav Nyquist, and Christian Dvorak for some while.

Some of these forwards are better than others, and some carry more risk than others for contracts and likelihood of performing to the level the Jets should hope for.

Final Thoughts: If I were Cheveldayoff…

I’d be a bit nervous about the strength of my forward roster. There are a few holes, and also a few candidates for some negative regression this season. While people think I’m someone gung-ho for bringing in the youth and trying out prospects, those still introduce risk, and the current roster isn’t designed to take too much risk.

Re-signing Ehlers and bringing in Suter or Bjugstad in cheap would be a pipe dream, but is the best-case scenario.

The team needs some stronger performers up front, otherwise the former President’s Trophy team may be more of a Wild Card team than another Central Division powerhouse.

That said, the Jets don’t have to solve all their problems in free agency. It’s hard to do so for any team, even those who are more attractive suitors than Winnipeg. The trade market has historically been kinder to Winnipeg, and they could go shopping this summer and/or by the trade deadline… just don’t add pieces like Tanev and Schenn again.

Speaking of Schenn, it’s time to ship him out, and it’s time to end the Logan Stanley experiment.

Bonus section: Scouting Notes From Scouching

If you don’t know Scouching.ca, you should.

Will is the new wave of scouts, combining analytics with the traditional eye test. He’s a great read on his blog or watch on Twitch. Check him out!

Here’s what he says about some of the Jets’ first rounder:

Boumedienne is a really interesting blank slate to develop over a few years. A very mobile skater in multiple directions, Boumedienne has some impressive offensive tools with some great timing to create for others. He can catch defenses sleeping with a quick pass or skill move that shows some real potential. Impressive, considering he's one of just three 2007-born players playing NCAA hockey, and he played quite a few minutes. The defensive rush positioning and physical play along the boards make him a bit leakier at times, and his offensive mindset leads to a few too many risky turnovers, but there's an interesting player here that really seems to resonate with what it seems their strategy is.

And about Winnipeg in general:

I think considering they only had two top 100 picks, they did pretty well for a contender. Owen Martin is a really smart and capable forward with a great sense for the game and some skill that could develop well. Jacob Cloutier is such a fun swing late that could develop really well as well. A smaller high skill guy, but really energetic and I think with time will put more offense together and could be a nice pickup long term. Another year, another strong class from Winnipeg.