Most Habs fans and media believe that the Canadiens should retool at the deadline. I am of the same opinion. I really think this is the time for the Habs to retool, not rebuild.
I would like to see this happen under the watchful eye of a new management team and would love to see Gauthier and Gainey let go. As much as I respect Gainey, I don't think he made the right choices when he retooled the last time. It was one thing, that no other GM would do, to trade for Gomez, but to throw in McDonough was too much! I have no confidence in Gauthier being able to maximize any trades!
Montreal now has a window to make some positive changes to move forward with a younger, better balanced team that could be a solid playoff team for years.
Right now I would say that Gill, Campoli, Kostitsyn, Kaberle, Weber, and Nokelainen should be dealt for whatever they can get. The deadline usually inflates values and teams that are under the gun to go deep in the playoffs tend to overpay.
I am not worried about the future of the defence. Nash would probably be with the team now if he hadn't hurt his shoulder. Beaulieu and Tinordi will be manning the point in a couple of seasons. Markov should just take the rest of the season off and focus on next season and Subban should take the summer to adjust his attitude. Other defence to watch are Pateryn and Dietz. With a season under their belts, Emelin and Diaz will be better and they are young at 25. Pateryn may be the closest to being ready having played in University. He has size and a bit of a nasty side.
Where the Habs lack depth, is up front. They have some possible talent in Bournival, Avtsin and Priebyl, but none of these players have an edge to their game. Avtsin and Priebyl have size, but the contending teams balance talent with grit. None of these players are "can't miss" prospects.
Here are my suggestions for trades that would bring the players I feel would help the Habs.
Plekanec, Weber, and Campoli to Chicago for Beach, Danault and Paradis.
Kaberle to anyone for a 4th or 5th round pick, anything better would be a bonus
Gomez for anything, but probably to Hamilton
Nokelainen for a 3rd round pick
Gill to San Jose for Petrecki. (if necessary throw in a 4th round pick or Pulashaj)
Kostitsyn to Nashville for Blake Geoffrion and a 5th round pick
This would give tha Habs a solid balance for the future plus the players they draft this season. One of which should be a goalie since they don't have any strong prosepcts in the system. This would also add some homegrown players that would be a bonus.