Such an odd trade without seeing who is on the board. If you're trading 2 2nds get into the lower 20s, sure. But giving up a 2nd to jump 5 slots seems shortsighted unless you know who is or is not on the board, no?
Purely hypothetical example - MON is REALLY excited by 2-3 guys (Hage, Stolberg, Greentree, etc.) who are all ranked around 20. By making this deal you're almost 100% likely to get one of the guys that you think is a large tier above what you're likely to get at 27. Then you look that about 10% of the players drafted in the late 2nd round ever have NHL careers of note, and that the Habs have more high round DP's than likely contracts spots, and the deal makes sense.
Honestly - same idea for the Sharks. They moved up 3 spots and likely guaranteed themselves a chance at one of the top 6 d-men in the draft (or Eiserman, YMMV) that they likely wouldn't have gotten at 14.
I'm a Hawks fan. Over the next 3 drafts they've got 12 picks in the top 2 rounds. TWELVE! That's literally insane, and that is why they moved a 2nd to the Isles to move up 2 spots in the 1st round and 4 spots in the 2nd. They're going to have more prospects than contract spots.