Funny how the people who preach "Yzerman will figure it all out" only ever speak in vague generalities. Those of us who don't view everything through rose colored glasses and who have actually done the math have a much more realistic view of things, and in that realistic view we're going to be losing people we really don't want to lose.
I only use generalities because the entire process is HUGELY variable. Projecting the future of 30+ players per team, plus 30 other teams trade values and needs, plus contract values signed, plus possible buyouts...etc. etc. There are tons and tons of different ways for all of it to shake out, but, the basic premise remains the same.
Putting the thoughts more math-y, look at the situation additively:
Palat(5.75)** - Johnson(5.75)** - Kucherov(5.25)*
Drouin(5.25)* - Stamkos (8.5) - Callahan (5.8)*******
Killorn (4.45) - Namestnikov (1.958) - Brown (1.25)
????? - Paquette (.812) - Condra (1.25)
Hedman (7.875) - Stralman (4.5)*****
Koekkoek (2)**** - Coburn (3.7)******
????? - Sustr (3.5)***
Vasilevki
?????
Starting with those under contract for 17/18 who will likely be back; Stamkos, Killorn, Brown, Namestnikov, Paquettte, Condra, Hedman, and Vasi at a total cap hit of $29.575Million.
*Bridge Kucherov and Drouin, they're divying up about $10.5 million in cap space on 2 or 3 year deals that see them still restricted on the other end. Sure it's cheaper overall to sign them long term now. The cap structure of the rest of the team just doesn't allow it, yet. But it will in 2-3 years. I think Kucherov gets higher AAV than Drouin. It's not the worst thing to delay their big pay day until their next deal. Much could change in their own games or the team structure overall in those 2-3 years. Worst case scenario, one costs us the other down the road when unable to afford both. That time isn't now. For now pencil both Kucherov and Drouin in at a combined $10.5 for a total $40.075.
**Cannibalize Filppula's cap hit into Johnson and Palat's raises. Whether trade, expansion draft, waiver claim, or buyout Filppula will be gone because Tyler and Drej made him an affordable luxury two seasons ago. Now that they're ready and deserving of making more and it will come at the expense of the luxury that was Filppula. Buyout or trade return cap ramifications will be dealt with via other means. For discussion purposes divy Filppula's $5 M on top of Johnson and Palat. Average them at $5.75 each realizing there may be a disparity between their next contracts depending on how each plays next year. I don't see either wanting to rock the boat or jump ship via offer sheet, they genuinely seem to love and respect the opportunities they've earned in this organization to date. Adding $11.5 for both combined raises the total to $51.575.
***Sustr keeps slowly progressing. Doesn't stick out enough to merit a monster raise, plays enough meaningful minutes to merit a decent raise should it go to arbitration. Settles on a 2 or 3 year deal in the $3.5 area. Total = $55.075
****Koekkoek gets a similar 2 or 3 year bridge deal similar to what Sustr is coming off of, sub $2 M AAV. Total = $57.075
At this point the young, future moving core is re-signed. Hypothetically, I'll project a cap increase of $2.5 M. Only basing this increase on the addition of Vegas, dividing the current $73 M by 31 teams adds $2,354,838. A nominal increase in other aspects rounds it off to $2.5. I realize this is a BIG variable. There is no guarantee the cap will grow. Nor is their anyway to accurately predict how much it will if it does. That said I think +$2.5 M is a conservative estimate of cap growth that is at least somewhat realistic. So Total cap space $75 million minus $57.075 of the above outlined core leaves $17.925 to fill 2 wingers, 3 defensemen, and a backup goalie. Now look what we can do with the remainder as relates to other veterans currently under contract.
*****Stralman provides incredible value as a top pairing defenseman at $4.5 M. His contract length coincides nicely with the need to one day give Kucherov and/or Drouin bigger raises than the bridge deals suggested above. He has a role, value, and fills a need. Of all the vets I think he's the first most would like to retain, myself included. Keeping his $4.5 brings the total to $61.575.
******Coburn I think stays for similar reasons to Stralman. His re-signing at a lesser amount demonstrated how much he wants to stay and play for this team. His role versus his cost mean he is not terrible value over replacement. Say Coburn stays at his $3.7 M, bringing the total to $65.275 leaving about $9.725 to fill 2 wings, 1 defenseman, and 1 back up goalie.
*******CALLAHANSANITY!!! Elephant in the room, skeleton in the closet, biggest thorn in the team salary structure's side. Fitting his $5.8 in on top of all above only leaves $3.925 to fill the 3 remaining holes with AHL promotions that aren't ready, reclamation projects, and/or washed up has-beens. Dumpster diving du jour. Callahan has the ability to come back and contribute significantly. He also has leverage in determining his future via his NMC. To fit him in, by necessity, means losing Coburn and/or Stralman to compensate and have enough to fill the remaining holes. If able to move Callahan's salary out we could re-sign Boyle, let Garrison play out his contract, and still have enough space to fill the final wing and BU goalie holes. Moving Callahan out at little cap cost going forward is the biggest, most fairy tale-esque part of the entire equation. If Callahan wants to remain, he will. Personally, I expect he is gone before the start of the 2017/18 season. Just business.
********Garrison - buyout as last resort. Incredibly cheap buyout for benefit ratio. $2.5 M dollars owed means his buyout would cost ~$825 k the next two years, clearing $3.674 M cap space in 17/18 for a cap penalty of $825k in 18/19. I think it far more likely Garrison gets traded after the season to one of the teams that lose a valuable top 4 defenseman in the expansion draft for non-cap relevant futures. A shame since he does a good job and we don't have a ready replacement, again, just business.
*********Boyle - would love to bring him back to push Paquette back to the wing or off the team. If he's willing to stay on another discount deal (-$2.5M a season) AND Callahan's cap hit gets opened up then I think both sides work things out to keep it going.
10*Assuming the three remaining holes (1W, 1D, 1G)are filled with AHL promotions ~$900k each that leaves $1.225 M.
TLDR: Easiest way out is finding an exit from Callahan's contract. All other pieces are fluid enough value wise to not hinder keeping the core together even if forced to keep Cally. Sacrificing the vet deals allow keeping the core.
CAVEAT: I know nothing, and all of the above are only my opinions. I don't think they're entirely unrealistic nor uncharacteristic of the generality of how good teams renew their rosters around core elements that they commit to and how they transition from one core to the next. My only leap of faith involves believing that Yzerman has already shown himself to be quite skilled putting cap compliant rosters together capable of competing, and expecting that to continue.