Curious where you found current value chart? Not sure if it is static, but I think the Habs would need to fork over more based on the 2022 chart I saw.

Value charts don't work on the draft floor...

You have buyers and you have sellers. Both of them think they're getting better value out making the trade vs not making the trade. And you won't see a trade like this before the draft.

You're the Canadiens, and there's a guy you really like at 20 or 21 wherever the Rangers are and he's still up there, so it's pick 18, the Rangers want to take Gabe Perrault, and then boom, right before the Rangers pick, Perrault gets swiped, Drury's looking at his options: "take this guy ranked 30th like Daniil But or whatever with a pick at 20 or trade down and increase your assets... Montreal's offering such and such, Dallas is offering such and such" and then Drury pulls the trigger on a trade.

I'm not sure it was current but the values were ~8 "value points" above giving EDM & NYR more value than their original pick is worth. It was just a quick google search for a value chart, I wouldn't read too much into it, just an option.

I like the idead of the Habs getting another first in this draft, even a late one.

The Rangers GM would have to be looking to get fired if he accepted that offer. Drop 2 or 3 maybe even as much as 5 or 6 spots sure but dropping 14 spots costs more than that.

So Montreal trades the #69 & #101 picks to Edmonton for the #56 pick, which they then trade to New York along with the #37 pick for the #23 pick.

I could see Edmonton being interested in this kind of trade because they only have one pick in the first 5 rounds, so they may prefer quantity over quality, but most likely they'll want to wait until their pick comes up and see if they like somebody who's still available. By then the 23rd pick will already be gone, so if Montreal's goal in this is to get another first-rounder, that won't work for them. Would Edmonton still be interested if Montreal insists they make the trade before the draft (or at least before the 23rd pick)? Maybe they would be, but I think the deal would be less appealing since there would be less certainty around who they'd be giving up. Montreal might have to throw in one of their other 4th-round picks.

So what about the New York part? Their cupboard isn't as bare as Edmonton's, but they also might be interested in giving up quality for quantity. Going from #23 to #37 sounds like a big drop though, and I'm not sure #56 is enough compensation for that. I'm almost certain that they'd insist on waiting to see who's available at #23 before agreeing to that. Montreal would have had to have already made the deal with Edmonton by then, so they'd have to be happy with that trade regardless of whether New York trade goes through, unless Montreal tells Edmonton why they want the #56 pick, and Edmonton is willing to let Montreal back out of it if New York refuses their offer.

With #37 Montreal could potentially pick the goaltender M.Hrabral so I don't see them trading away this pick. Again mtl could still pick him up at 31/32 with the Floride pick if they still have it.