If they are not in play-off contention by the deadline what they probably should do is (and this is extreme and they wont do this much even though maybe even more could be done, as will re-tool to a lesser degree)...
Fire entire coaching staff. Bring in an established, young HC with a history of success in AHL or AHL and then NHL assistant. Pick person wisely and one who aligns with what want to be and players have going forward.
If Giroux wont re-sign for a reasonable deal? Move him. Sadly.
Move Risto.
Move JvR. 1 year left should help. Try and not retain but bring back a useful, similar length, slightly overpaid depth player to squeeze out youth/pick value.
Move Braun.
Move Jones.
Preferably, especially in Giroux and Risto cases? For youngish talent that might be on cusp of breaking out. ESPECIALLY if someone who think *might* have a shot of being a 1D or 1C. But that will be very hard. And would have to identify right person.
And if can move 1-2 of TK, Farabee, Sanheim or Provorov to potentially get a future 1C/1D? Bite that bullet. But CANT move more than 1-2 of them unless something similar/better coming back as actually good, young-ish players. And all heading for down-ish years that means wont be at full value.
JvR, Braun and Jones? Yeh, picks and maybe a bit of salary back in JvRs case.
Try and move Brassard, Yandle, Thompson even if just get a couple of later picks between them.
Atkinson, Hayes and Ellis with their cap length though, and given that were Fletcher pick-ups, well, here to stay I guess. But in an ideal world? Move one or more for value.
And accept that next year, if get right coaching staff, well, probably a cusp-playoff team again.
But issue is... even with a "re-tool" of this degree, which is likely about most that will happen... how many actual legit 1C and 1D in NHL have been traded in last 15 years when still young?
Eichel? Yeh. That was the boat. But a gamble.
Seguin, Zibanejad and O'Reilly? But none "even" Giroux level.
Spurgeon? Great player but a fluke when he was still a "meh" prospect.
Sergachev? Traded for a top prospect at time... albeit Montreal were silly to move D for W prospect of similar level.
Hamilton? But he likes museums so lost value.
Suzuki? A maybe... and moved while a prospect.
That is:
5x 1C (4 who are below Giroux level at his best)
3x 1D
who have been moved from draft team before ~27 or so in the last 16 years. Maybe I am missing someone. But it is rare and half the time a luck exercise.