It’s been a little while since we talked about all the ways Winnipeg’s offseason could go horribly wrong.

Barry Trotz has Jets fans feeling optimistic. Pierre-Luc Dubois and Adam Lowry are playing well for Canada at the World Championship, while Nikolaj Ehlers’ Danes beat Canada for the first time ever and Nate Schmidt continues to be a gem in every dressing room he visits. Andrew Copp could even help get the Rangers into the third round of the playoffs, giving the Jets an extra first-round pick.

The questions you asked in this mailbag could take those good vibes and turn them completely on their head.

What happens if Dubois signs an offer sheet? Is Connor Hellebuyck unhappy? Are private coaches like Adam Oates putting individuals too far above their team?

Those are just a few of the items we deep dive today, along with predictions for Mark Scheifele and Blake Wheeler’s futures and a quick story from my youth on the ice.

It’s true, this here writer did in fact grow up playing hockey. I just wasn’t very good at it.

Note: Submitted questions may be edited for clarity and style. 

Do you believe the Jets will let Montreal make a ridiculous offer for Pierre-Luc Dubois and, if Montreal does, would it be worth matching? What would the positives and negatives be of such a deal, maybe upward of $7-8 million per year? — Brad B.

I think the possibility of a Dubois offer sheet exists. Let’s talk about the most important issues.

Will Dubois sign with Montreal or another NHL team?

The first thing to know is that, as a restricted free agent, Dubois is eligible to be signed to an offer sheet unless he files for arbitration. The deadline for him to file is July 17. The Jets, for their part, probably hope Dubois files for arbitration so as to guarantee that he’s under contract with them next season. (Note that Winnipeg can keep negotiating toward a long-term deal with Dubois until his hearing begins; otherwise, they’ll be looking at a one-year deal.)

If Dubois chooses not to file for arbitration, then he will stay eligible to be signed by another team. Note that this means it’s not about the Jets letting Montreal make an offer or not; it’s about Dubois’ decision to file or not to file for arbitration. (Sure, Winnipeg could sign Dubois well before July 17 but I don’t think that’s going to happen. Look back to 2019 when Kyle Connor and Patrik Laine signed their RFA deals in September — it’s completely normal for big-ticket RFA contracts to take a while.)

Now let’s get to the intrigue.

If Montreal and Dubois do come to an agreement, Winnipeg will get a week to match the Canadiens’ offer. If the Jets choose to match, great: they get to keep Dubois for whatever dollars and term he was happy to play for in Montreal. If the offer is so ridiculous that Winnipeg can’t or won’t match it, the Jets will be entitled to compensation.

Please note that strictly for purposes of draft pick compensation, the AAV is calculated by dividing the total contract value by the number of years offered or five years — whichever is less. This means a one-year, $8 million contract and a seven-year, $56 million contract pay the same money per year and have the same cap hit but the seven year contract yields a greater return, compensation wise. (In the first example, $8 million divided by one is $8 million. In the second example, $56 million divided by five is $11.2 million.)

Note that it costs a team nothing to sign an offer sheet worth below $1.386 million. I don’t think this means Winnipeg should be worried about losing RFA forwards Jansen Harkins, Evgeny Svechnikov or Mason Appleton by this route but I’ll note that, as arbitration-eligible RFAs, this conversation applies to them.

The first thing I’ll say is that a contract between $7-$8 million, as you suggest, is not ridiculous at all; I think Winnipeg would love it.

The second is that I think Winnipeg wouldn’t think twice about matching any Dubois contract up to the $10.504 million mark. Two first-round picks, one second-round pick and one third-round pick may seem like an attractive compensation package but you’d need Montreal to be truly awful to get value out of those picks. I can’t see the appeal in betting on the Canadiens to add Dubois and remain a lottery team, then take two of their first-round picks, and then wait for those players to approach Dubois’ present value. Yes, a $10.4 million contract for Dubois would be a pain in the cap but losing him for anything less than full value would hurt even more. He’s probably an ~$8 million player over the life of his next deal; given that he’s 23, scores at 0.75 points per game and may already be Winnipeg’s most complete centre, I’m not particularly worried about the inefficiency.

Let’s say the Canadiens cross $10.504 million, bringing Winnipeg’s theoretical compensation for Dubois up to four first-round picks. Is that worth letting Dubois walk?

One way to evaluate that is to look at the projected value of draft picks compared to Dubois’ projected value in any given season. We all know that the first pick is worth a lot more than the fifth pick but how big is the difference — and how does that compare to what Dubois is worth now?

This chart shows historical values of a player’s first seven seasons at each draft position.

To follow through on this thought experiment, Dubois finished the season at 2.2 Game Score Value Added, Dom’s in-house model.

If he maintains that value for the next seven seasons, Dubois will accumulate 15.4 GSVA in that time.

If you divide Dubois’ 15.4 GSVA by the four first-round draft picks, we reach 3.85 GSVA per pick.

This value corresponds with an average pick position between 21st and 22nd.

Certainly, Dom’s model is just one paradigm and not necessarily The Truth Of All Things. Still, it appears as though four first-round picks for Dubois would be a good bet for Winnipeg to make — in a vacuum. But letting Dubois walk, even in exchange for four first-round picks (and even if those picks represent good value), creates a massive problem. It either signifies that the Jets are in full-blown rebuild mode or that they need to find a player of Dubois’ calibre immediately just to get back to where they were.

And we know that finding even one Dubois is a tough task; it cost Winnipeg Laine and Jack Roslovic to acquire him (and a third-round pick.)

The game changes if you take the perspective that Dubois will absolutely not play in Winnipeg for the next seven years but if we start running through all of the permutations I won’t get to anybody else’s questions.

So, Brad, I think Dubois is in more control of his offer sheet destiny than Winnipeg is. He can choose not to file for arbitration, keeping himself available to be signed. I also think that almost any offer sheet — especially any offer sheet below $10.504 million AAV — is an automatic match for the Jets. If Dubois truly won’t sign in Winnipeg and truly must play in Montreal, then perhaps there is a trade to be made that works out more in Winnipeg’s favour.

Is Connor Hellebuyck unhappy in Winnipeg? One thing that surprised me at the end of season newsers was the tidbit about him being willing to stay so long as the team wasn’t going to rebuild. It feels like a lot of people missed that and are just focused on running Scheifele out of town. There are only two years left on his contract and with that tidbit coming out it feels unlikely he will sign his next deal here. Should we be starting a Hellebuyck trade watch? — Alexander H.

Hellebuyck said he’s happy to stay with Winnipeg long-term as long as the plan is not to rebuild, as per Elliotte Friedman in 32 Thoughts a few weeks back.

For some, this item was a bit of a shock. Hellebuyck has been a massive part of Winnipeg’s success, whether in the glory days of 2018’s playoff run or during his Vezina Trophy-winning 2019-20 campaign — a season so good it kept a team playing lottery-quality defence on the cusp of a playoff spot.

His most recent season was not as good as the ones that came before it but Hellebuyck has largely been the one thing Jets fans could count on in recent years.

Could he really be on his way out?

Personally, I don’t read a lot into his comments as they specifically pertain to a rebuild. To me, they’re a little bit like the difference between telling your partner “I’ll love you forever” and “I’ll love you forever unless you start treating me horribly.” Sure, the second option leaves an un-romantic sounding exit on the table but horrible treatment is a bigger issue than escaping horrible treatment.

If Winnipeg embarks upon a rebuild — a path I don’t expect — then Hellebuyck would rather play somewhere he can win than go through an encore of 2019-20. Where’s the fun in getting shelled ad nauseam, knowing that even the literal best season at your position won’t be good enough to make the playoffs? (Also, if Winnipeg embarks upon a rebuild — once again, a path I don’t expect — then it had better trade Hellebuyck, else he’ll win too many games to assure the Jets get the best available draft picks.)

I do read an awful lot into the fact that Hellebuyck is a free agent in 2024. The idea that Winnipeg needs to get good this season or next to keep its most important player puts tremendous pressure on its offseason decisions. (Of course, I’m assuming that Hellebuyck returns to top form; we know that goaltending is difficult to predict with as much certainty as other positions.)

If Winnipeg retains Dubois long-term and Scheifele comes back (or Winnipeg gets a great return for him) and a new head coach leads the Jets back into the playoffs, then perhaps we see Hellebuyck sign an extension during 2023-24. If not, no part of me would be shocked if he wanted an opportunity to win in another city.

Put another way: I believed him in when he said, “I only have one goal left, and that’s to win the Stanley Cup, so anything other than that is kind of a wasted year.”

Are private coaches undermining team coaches? (i.e. Adam Oates). Have there been rumblings in the league about private coaches being a detriment to team play? Has Adam Oates’ commitment to having players avoid injury at all costs created players that neglect the defensive side of their game by avoiding those dirty areas, etc? — Phillip G.

My only experience hearing Adam Oates speak comes in the form of this video, posted at Sportsnet.

Phillip, I’ll admit: When I listen to Oates talk about Jack Hughes taking contact “when he shouldn’t” after scoring a goal, I do hear a perspective of self-preservation above all else. Of course, that video is just one example of Oates’ perspectives. It doesn’t say players shouldn’t play defence or should give up on team play. (You should probably just watch it so you form your own opinion; mine may be a bit harsh.)

Oates played 1,337 regular season NHL games, scoring 1,420 points, and added 156 points in 163 playoff games. I haven’t reached out to Oates for purposes of this mailbag, but I know I’d take his opinion on body positioning over mine.

Oates markets himself as a skills coach who “is able to identify the nuances within a player’s movements, skill set and thought process that are holding that player back from reaching the next level.” His website says that “Safety is my biggest concern in a player’s game. When I first speak with a player, I ask him to send me some game tapes. The first thing I’m looking for is does he ever put himself at risk and, if so, why? From there I form a plan based on what the player is doing well and what needs to be worked on.”

His Jets client list includes Scheifele, Wheeler, Josh Morrisey and Brenden Dillon. Former Jets include Copp, Tyler Myers, Andrew Ladd and Nate Thompson.

When Wheeler came back from his knee injury and I noticed him attacking the middle of the ice in fresh ways — with less pace, but with a greater capacity to read and react to the defence in front of him — I asked where that development came from.

Wheeler: I think you have to find new ways to create time and space. I think that throughout my career, I have thrived when I play with guys like Mark (Scheifele), for example, who creates a lot of time and space for me. I thrive in those situations when I have time and space. I think the evolution is defencemen skate a lot better than they used to. That’s just a fact. You see maybe there’s a couple guys in the world that are burning around defencemen. Those guys were pretty special players. So now, you’ve got to find ways to play within the balance, get in the corners and win battles and create a little time and space for yourself. It’s something I worked on a lot. When I was hurt I got to spend some time really working on things that I wanted to work on. I think that time off I made the most of it to evaluate my game and how I can try to build on it a little bit and continue to have success here in the later stages of my career.

I like this exchange because we have one 1,000 game NHL player calling another 1,000 game NHL player “brilliant” and explaining how Oates’ insights have helped him. I also like it because it doesn’t start with me saying “Tell me how Oates influences your game” — it’s more of an open-ended question about a change in the offensive zone that I had noticed in Wheeler’s game.

Again, I’d take Wheeler and Oates’ perspectives above mine any day of the week.

At the same time, I would be lying to you if I said I’ve never heard someone in the NHL question the impact of private coaches on team play. I don’t expect that debate to go away any time soon; I expect it to grow as the use of private coaches becomes progressively more common.

All right Murat, what we’ve all been wondering and we need a stay or go answer … Does he stay or does he go? (1. Mark Scheifele 2. Blake Wheeler) — Craig N.

I think a one-year deal for Dubois sees Winnipeg make every effort to bring Scheifele back, despite his end-of-season comments that appeared to put his own needs above that of the team. To go from Scheifele and Dubois to the risk of neither seems like the rebuild that Hellebuyck wants so badly to avoid.

If Dubois signs long-term, I think Winnipeg is in a much safer spot to trade Scheifele.

Go back to the Dubois section of this piece, though. His deadline to file for arbitration is a week after the draft. Even if he files, his contract situation could remain unresolved until well into August. That would make the timing of a Scheifele trade all kinds of difficult — much more difficult than if the Jets were able to shop him in the lead-up to the draft.

I think the nature of Scheifele’s exit interview with Kevin Cheveldayoff is an important question. Can any hardships be walked back? Can growth happen here in Winnipeg?

If the relationships are OK, then perhaps Dubois and Scheifele each play out the year and Scheifele gets traded next summer.

Wheeler: I think he stays, although it is interesting to note that his full no-movement clause becomes a five-team, modified no-trade clause after the draft.

Who is your favourite Jet right now and why is it Ehlers? — Cameron B.

This is a bonus question and one I don’t get to think about too much.

I typically gravitate to players who are almost as skilled as the very best who get to be included among the best of their era by virtue of heart or determination.

I grew up idolizing Ryan Smyth — in fact, I wrote about it in 2020 — and I think he fits the bill on that front. Present day favourites on this front include Ryan O’Reilly who is obviously a wildly different player type but whose unwavering commitment to making the right play every single time is something a lot of players talk about but few players accomplish. If I spent more time watching the Eastern Conference, I’m sure Patrice Bergeron would be high on that list.

I also have a lot of time for the Fernando Pisanis and Nick Pauls of the world — playoff heroes who play such an honest game that you can’t help but respect it.

Ehlers checks a lot of boxes I like: dynamic, explosive, horribly underrated … But honestly, he’s way too fast and skilled for me to relate to. The highest level of hockey I played was U16 for Upper Canada College in Toronto and, despite leading that team in goals and points I wouldn’t have stood out as fast or skilled even at that low level of hockey. My shot was a muffin. I skated so awkwardly I nearly got cut outright. I had tunnel vision, seeing only the battle that was in front of me at any given moment and almost nothing else on the ice. I was lanky, I seldom hit, and the one fight I ever got into was with a goalie who …

I could go on but I think you get the point.

The one thing I was good at (for what I hope I’ve made clear was not a high level of hockey) was trying so hard and having so much energy that I was difficult to contain. Secondary skills included “taking infinite amounts of abuse in front of the net” and “being more patient than goaltenders were from two feet out.”

So Mathieu Perreault? He made sense to me. Ehlers makes no sense at all.

Anyway, to actually answer your question I’ll choose Paul Stastny because I don’t think he gets enough credit for how good he is at 36 years old. I think he gets as close to 100 percent out of his current skill set as is possible and I can’t help but admire that.

(Photo: Darcy Finley / NHLI via Getty Images)