Massive overpayment for Galchenyuk!

I hope MTL doesn't move Chuky period. Pacioretty is the guy I think Bergefail will focus on moving. Trading Patches accomplishes two things at once (whereas trading Galchenyuk only does 1): it'll fix one of the Habs current issues (getting a Center or a top 4 offensive LD) and provide a new change in Leadership with one of Weber or Gallagher getting the Captaincy (both are equally deserving).
Also, Pacioretty I believe also has more value in the eyes of most GMs due to his pedigree as a 5 time 30 goal scorer. Galchenyuk hasn't accomplished that (yet) but certainly has more potential/skill than Pacioretty does. I'm much more willing to take a chance of keeping Chuky.

How about

To CGY -> Pacioretty + McCarron + 2018 MTL 2nd rd pick (35th overall) + 2018 EDM 4th rd pick (102nd overall)
To MTL -> Brodie + Bennett

Basically 1v1 Patches for Brodie, but Bennett has to be included so MTL gives an extra three assets, including 2 picks that CGY are lacking this upcoming draft, and a Center to replace Bennett down the depth chart.

In the leafs trade, I think you can get one of the two, but don't think the leafs will trade both.
I would say maybe Stone + 2019 4th for Brown, Hamonic still has something to show and I wouldn't want to trade him at a low value (not that Kapanen and Brown are bad).

THe MTL trade, I like!
Chucky and Bennett could both use a change of scenery. I think remove the pick and Lazar.

Perfect in term of trade value

One of the attractive issues with Chucky is he is 26 and has term. Too often I see 30 year old forwards decline quick as this is now a young mans game. Don’t think I would part with both Bennett and Brodie with Patchs as the main piece coming back. Too risky with age and no term.

Small corrections. Chucky just turned 24, even more reason for MTL to keep him. and Brodie will be 28 by the time next season starts and Patches is 29, yes he is approaching 30 but the age gap between him and Brodie isn't that great of a gap. so 1v1 Patches for Brodie still makes sense imo. I'll say fair enough if CGY isn't interested in him, but I'm almost positive that he gets moved way before Galchenyuk does (I hope so anyways lol).

I wouldn’t do that Montreal trade, speaking as Montreal. Bennett and Lazar so far are busts, Bennett might still make it to his potential but don’t think Montreal is the organization he gets the support to do it. Galchenyuk has still produced under some of the most scrutiny in the NHL and still has another level he can reach, I keep him instead of Bennett.

I could see something with Brown-Hamonic as the general framework. Leafs would hope Travis could find his game back and Flames would hope Brown could produce more with consistent minutes/responsibility in the top 6.

Even if the leafs added a high draft pick it'd be worth the risk for me.