Ehlers: I think he will eventually end up re-signing. I'd have given it a 30-40% at this point last year or rather after the playoffs last year. After the season he had, the vibes around the team (could be if not is the best locker room as of the league right now) and the upgrade in utilization he got on the PP, I think right now he's on board with the Jets being a very good pick for his next contract. I have no doubts that he'd be able to sign a contract on another team with top forward minutes and 2M more per year than what Chevy is going to offer him but Nikolaj Ehlers doesn't strike me as the type of player that is chasing the biggest possible contract and I also don't think he has any problems with Winnipeg weather or market wise. Right now, these 30-40% I would categorize more in the range of 60-75%. I for one am confident. But only because this season went so wall and showed actual improvements in the love he was shown on the ice. I also feel like Arniel might be the first coach being fine with giving him a little bit of a longer leash, resulting in Nik having more fun in his role.
Overall, it feels very similar to the exact same situation last year at this time with Scheifele and Helle.
Tanev: Totally depends on the money, just like last time. Winnipeg and Brandon Tanev is a match - we know it, Brandon knows it. The only question is, is he going to be fine with giving this "match" a discount money wise and I think, this time, he will. Last time he understandably took the cash road. Therefore, I don't think it will be his main priority this time. I think his priorization might have shifted a little bit more towards "wanting to play on a contender" instead. It's just a natural process kind of thing in the career of a cap restricted league for a sport professional like him IMO.
Appleton: Dear god if this franchise somehow ends up re-signing Appleton over any out Tanev, Barron or Kupari, I am going to be pissed about it. I would like to have Appleton's time on this roster come to an end. It's nothing against Mason, sure he's a great kid but oh boy is he replacable at this point in time. Like over the last 2-3 months, I honestly don't know what he even does. Except create big mistakes or cost us, you gotta give him that. He surely is not a negative for us. But oh boy is he also not a positive, lol. Honestly it seems like his hands got worse, his shot less dangerous, his skating in general slightly worse. He also doesn't seem to get stronger or like feistier... Like seriously, what is Appleton doing good at this point? Please let Chibrikov naturally replace him starting this summer. He is a perfect replacement for him. Not because he plays the exact same game (thank god lol) but he has the skating and desire to win every puck battle that is needed while having a lot better offensive skills and therefore way higher upside longterm.
Barron: Is going to be re-signed. This season was a "show me" year for him to me for his future on the roster and he truly stepped up. It's not a huge step bit it's a step. I somehow even feel kind of excited about Barron over the last weeks. You really feel like he's starting to have figured out how to use his frame and strength in order to be dangerous in the o-zone. I think he has still so much more potential. Not necessarily top-6 potential but upper third in the league third line potential for sure.
Vilardi: This is actually the biggest question mark to me on this list. I am quite concerned actually even about re-signing him. Do I want him re-signed? Sure, of course. Do I think that his long-term contract has the potential to be a disaster? Oh boy, definitely. This season he's tied for 74th in points, 55th in goals, and 88th in assists. His plus-minus rating tied for 134th. He also had 2.84 points per 60 minutes. And the 55th in goals part to me is the big thing.
Over the last two seasons combined, Vilardi has 1.05 Goals/60 the puts him right in line with Alex Tuch (4.75M), William Karlsson (5.9M) and J.T. Miller (5.25M). But also just below Panarin, Stützle, Benier and Kaprizov all making between 7M and 11.6M. The Vilardi re-signing is all about making sure he's going to get paid in the Tuch, Karlsson and Miller range but as you can see, it's really a tough spot. His agent will push hard for 7-8M and if Chevy cannot win this battle, he either doesn't re-sign (I think it's a quite likely scenario eventually because of that) or he stays for 7 or even 8M and that would be a problem because Gabriel Vilardi is not a play driver nor can he create his own chances. He needs to be set up and he needs players that draw attention. That is the reason why he's a great complimentary piece to Scheifele and Connor on that line. I you'd switch Vilardi and Ehlers around, just on our roster this season, the changes in especially G/60 would change drastically. We'd get completely different numbers. And I really hope this doesn't create a big problem both sides won't be able to overcome once negotiations eventually start.
You probably realized that I didn't even mention his slight long-term health issues because we all know about them. It is of course another small concerning part...
tl;dr: I am really scared they end up signing him for 7x7 or so. I personally wouldn't do it.
Fleury: I would be fine keeping Fleury around for another 700-800k contract for sure. I don't think there are many defenseman in this league better than this for below 1 M. I think he's a pretty good 7th d-man for that role. If you need to cut him because of roster spot reasons, then so be it.
Kupari: I am still undecided and would want to see his playoff performance + another season next year.
Samberg: Sign that man, we need him. I would hope for something aroudn 6.5Mx7 (could even see it end up being 6Mx8 or so) which ends up being a crazy good value contract in year 2 or 3 of that contract and look decent even at the end of it. It might be a bit low but I am 100% confident Samberg loves it here and has no interest in leaving at all.