First of all Drouin is by no means a 2nd line player. He scores at a third line rate (228th in 5v5 P/60 over the last 3 years despite constantly playing with the best offensive players on the Habs). His defense is also awful. So really (at best) he's a third line scorer who is awful defensively. Like he's a negative WAR player for a reason. Paying $5.5m for a third liner (tbf Drouin's probably worse than a third liner) is certainly an overpayment. Drouin isn't trending upwards, he's
trending downwards. We need get him off the books ASAP, while he still has value. I don't think he's currently considered a negative asset around the league, and the Habs wouldn't have to add anything to unload his contract, but I don't think that'll be true for much longer.
Now on to the other point. I don't think the Habs are that far away from being a good team tbh. I think if the young guys step up and some prospects pan out, we could be sitting on a really good team in a couple of years. Remove the dead weight, and you've got more than enough room to keep the rest of the band together. Let's do the math, shall we?
Note: I'm using CapFriendly for all this, so that's where I'm getting the final numbers.
This offseason the only critical re-signings we need to make are Domi and Mete. Everyone else can be let go (and we can re-sign the ones worth keeping for under $1m). Remove Drouin (bad) and Chiarot (Romanov replaces him) and we're left with ~$22m in cap space with a roster of 21. Signing Domi and Mete long term should only cost around $10m total (Domi @ 6.25x5 and Mete @ 3.625x5 using Evolving-Hockey's contract projections), leaving us with a full roster and $12.3m in cap space going in to the 20/21 season.
Now projecting this far in the future is a bit of a fool's errand because rosters will have changed a ton by then, but this is more for the purposes of laying out that we can afford to re-sign all these guys. So, following the 20/21 season, we'll have 13 roster players signed with $38.5m in cap space. Add in a couple prospects making the team in depth roles (ex: Caufield, Norlinder) and we're left with 8 spots to fill and $37m to spend. Who do we need to re-sign? Armia, Danault, Gallagher, Kotkaniemi, Lehkonen, Petry, Tatar, and Weal. Now we can let Armia and Weal go, they're easily replaced (by Caufield and whoever plays on the 4th line). So now let's say Danault, Gallagher, Petry, and Tatar all ask for $7m a year (no chance they all collectively make $28m, but I'm just saying we could fit it in). That leaves us with ~$9m and all we only need to re-sign Kotkaniemi, Lehkonen, and 2 depth forwards. Those depth guys will make ~1.6m total, so really we're left with $7m for KK and Lehkonen. If both come in at ~3.5m (little high imo but not unreasonable on short term bridge deals) we just fit everyone in under the cap.
So if all that happens, what are we left with? We shipped out Drouin and Chiarot, and we let Armia, Folin, Weal, and Weise (and a bunch of other guys) walk as UFAs. We added guys like Evans and Caufield to fill up the departing forward slots, and guys like Romanov and Norlinder to fill up the departing defensemen slots. Not only that but we managed to keep all of Tatar, Danault, Gallagher, Domi, Mete, and Petry without going over the cap, and I gave all of them fair (if not more than fair) contracts. With a little roster surgery we should be able to afford all the important players' cap hits, the only real concern should be term.