5 for 8-40-2025 2nd
A 2025 pick isn't optimal but it's easily tradeable for a 2024 if sweetened with a later pick (See Tampa-Montreal trade)

5-31 for 9-17
Yzerman looking to get his guy? I don't like it personally because at nine you're looking at a tier of players down with likely Leonard, Benson and Reinbacher gone.
Knowing Montreal has a quantity of prospect but is lacking top tier ones this trade seems odd. I'd be more enticed by it if it were pick 37 instead of 31 but even there I might not bite on it.

5 for 15-Askarov
Don't know who adds here but seems pretty even to me as it is. 15 and 24 aren't enough to trade up in their desired 5-7 range and it's unlikely they trade away future picks as they enter somewhat of a rebuild so who's part of the deal? For Montreal Askarov is the only one that could make this work, the Canadiens are needy for a goalie prospect and could pick one early this year but what if they get offered one of the best ones now? Nashville would jump a couple tiers in the draft and could select the center piece to kick-start a rebuild while still holding on the 24OA pick they own. Montreal would get out of the first round with their goalie, 15 and 31.