Tricky part would be re-signing Hall and Domi next year.

That deal isn't worth it to Montreal.

This would be a pretty exciting trade...I imagine NJD would ask for Kotkaniemi instead of Drouin.

Would make the picks conditional on Hall resigning.

Petry would have to be traded for sure and 2 of (Tatar, Armia, Leks or Byron). Fleury should be ready for NHL at least to fill a RHD position, we just have to hope we'd have enough depth to fill out the bottom 6.

Maybe not in the longterm, but this coming season it would definitely make them better.

Kotkaniemi instead of Drouin would be a definite deal breaker. Chances are that NJ is going to have a hard time signing Hall and Vantanen anyway, so the Habs are helping them out by getting younger players on cheaper deals plus 2 firsts.

I don't really know about the Hall situation - but sounds awfully similar to Tavares last year. I don't think it is for lack of money...Hall wants to play on playoff team. Problem for MTL...if you subtract this many assets from roster, would Hall resign?

Maybe send them Caufield to reunite with Hughes.

If they would do it sure, but Drouin currently has much more value than Caufield.

I like your Idea of making the picks conditional upon Hall re-signing. I think the Habs are still a solid team minus those assets.

I think there are plenty of assets to deal without subtracting from roster

For Hall....(50% retained in 2019-20) at $3.0 million
Caufield
Brook
2021 1st round pick (conditional on Hall resigning)

For Vatenan...(50% retained in 2019-20) at $2.4 million
Ylonen+Fluery or Poehling
2020 2nd round pick

Would leave enough $$ to resign any RFAs this year and $12-15 million coming off books to resign Hall/Vatenan next year.

More I think of it, Hall to MTL makes tons of sense....