With the addition of Jeff Gorton and the absolutely atrocious season unfolding...the Montreal Canadiens may be looking to do something drastic and do a massive sell-off of assets and look to exchange valuable veterans for assets to form the future core of the team. While I doubt that they're going to do a full "to the studs" rebuild, it's possible...maybe even likely that some players that were previously seen as career Habs players move on. Here's a quick list of players and expectations. Note that this is just a fun exercise in speculation...if you think some of these are ridiculous...you're probably right.
There's been near endless speculation on players with 1 year left on their deals. I'd be shocked if any of these players are with the team once the trade deadline has passed. What I will focus on instead are players with multiple years remaining on their deals.
Carey Price showed that he can still be one of the best goalies in the world. With the recent stellar performances of goalies in their late 30's it's not unreasonable to see Price being a valuable piece for any team who would have him. That being said, a $10M contract is hard for most teams to swallow. Either the Habs would need to take back a bad contract or retain salary to get the most value from Price.
Who would be interested? That's a great question, I think that any team who is interested would need to be looking to shore up a need in goals, and either on the outside looking in or already a contender. Assuming that Price would only waive to be closer to home, makes this a short list. Seattle made a substantial commitment to Grubauer, and Vancouver did the same with Demko...neither goalies are necessarily part of the problem for these teams. Unless Price agrees to completely open his NTC to go to a team like Buffalo or Detroit; he's probably not going anywhere.
Gally's recent statements are certainly indicating that he's not exactly keen to be a part of a long-term rebuild. Gally is a leader in the Habs' organization and has skillset that should be in high demand. At $6.5M his value is good for what he brings, although the Habs picking up $1M or so of salary or looking for a third party to accept compensation to do so would likely increase the amount of teams interested.
Who would be interested? Well I'd be surprised if fewer than a dozen teams, but at the top of this list is IMO Vancouver. They're actually looking to turn the season around, and getting a player like Gally would help out quite a bit. Long term he's both a local boy and a solid leader both on and off the ice, so the long-term deal wouldn't necessarily scare them.
What could we get...well this is a tough question to answer, the Canucks' previous GM didn't exactly leave them with a lot of assets to make a deal like this easy to swing. OEL was their last big acquisition, but hasn't exactly proven himself to be great value...I could see a world where Vancouver would be looking to trade OEL for Gally...although the package would likely have to include a D coming back the other way. Could a Gally & Kulak for OEL and a 1st be possible...probably a great trade from Vancouver's perspective, but probably not from the Habs' perspective unless Gorton believes that he can either trade OEL and get more assets, or can rely on OEL to be a core piece moving forward. If Gally is looking to move to a contender regardless of destination, I think that Montreal would need to retain somewhere in the neighborhood of $1M and could get a "3 player package" a young roster player, a high-end prospect and a high draft pick (depending on the prospect).
It saddens to me to think about seeing the Powerhorse on any other team. He's young enough to still be in his prime if the Habs rebuild...but it's also what makes him so valuable. He's got a good deal, and contributes in a lot of different ways. With an 8 team no-trade list, it's hard to imagine it would be difficult to find a suitor.
Who would be interested? Two teams come to mind when I think of fit...the Boston Bruins and the Philladelphia Flyers. Both of those teams value players with size, grit and skill, and with DeBrusk wanting out of Boston, they would be a natural trading partner...if it wasn't for the bitter rivalry between the two teams. DeBrusk is younger and cheaper, and could likely be locked into a good long-term deal with Montreal. I would expect Boston to throw in sweetener, maybe a conditional 1st rounder to make it happen as there is far more risk on Montreal's side of the equation. Generally, I would expect the asking price for Anderson to be a good roster player and a pick.
Unfortunately, I don't see a huge market for Petry. The Habs would likely have to sweeten the deal and wouldn't get anywhere near his value...unless he's able to come back from injury in much improved form...this would be a net loss for the Habs, probably not moving...but if he does, it's probably packaged with a pick and maybe even some salary retained. IMO Jeff Petry still can be a top 4D in this league, but unless he proves it, he's got no value.
Toffoli is one of those players that's hard to quantify in terms of value. He's a reliable goal scorer who's decent defensively. He's not particularly big, physical, fast or agile...which suppresses his value. That being said, the Habs can likely get something for him.
Who would be interested? Any team that's looking for an upgrade on the top 6. I could see teams like Dallas, Detroit, St-Louis, and Pittsburgh having interest at the right price. Maybe a decent prospect or a pair of picks would be the most we can expect here. In Toffoli's case, cap space may be as important as the return we'd get for him.
Somewhat underperforming defensively-minded defenseman. That being said, he's hardly overpaid at $3.5M and will likely live up to that salary for the term of his deal. All things considered, could fetch a decent return for a team looking to get more depth or upgrade on their bottom 4.
Who would be interested? There's no obvious fit for Savard anywhere, which isn't to say that there wouldn't be interest. The return would likely be low...at best a 2nd round pick, although an underperforming young player who isn't living up to their salary is more likely. But if the Habs are looking to rebuild...the combination of cap space and picks is probably enough to get Gorton to pull the trigger on a trade of this type.
Overall, there's probably a few more names that I could add like Jake Allen, Paul Byron, Joel Armia, and Joel Edmundson. But I don't know if they would get enough in return to justify trading them.