Obviously take a swing at the top free agents, if they make it there like Marner Shesh, Rants.
Not sure if Bennett is considered a top, or 2nd tied, but definitely go for him.
I'm assuming he's retiring, but if not I'd honestly sign Fleury. I'd tell him he doesn't have to play even as a full-time backup of 30ish games. I'd take those 30 and split them up as around 20 for him and 10 for Dobes.
If he retires I look at Freddy Andersen. Probably don't have to make the same deal as he's hurt quite often.
If neither, maybe look at Allen and do similar to Fleury.
Depends how Dobes does the rest of the year he might keep progressing well and look more ready for the backup spot than not.
Jamie Benn- More than likely takes a lot less and stays in Dallas, but would bring him in for some more toughness, leadership and so his pos plays aren't against the Habs.
John Tavares - slow as f***, but a menace in front of the net and a beast on the dot. Being a leaf fan probably takes a lot less to stay, or doesn't want to play for the Habs, but I'd be interested.
Aaron Ekblad - RHD, cup winner and has been solid lately in his career. Would fill a need with leadership, right d. Probably cost a lot thought and be a bad contract.
Neal Pionk- he's a bit of a p-unk, but he's another RHD with some bite but the issue is he's a smaller, puck moving dman.
Yannick Gourde - French dude, pest, energy player. Problem is he'll be 34 shortly after next season starts. His offense is trending down, older, so if he's good with 2 years and cheap, like maybe 3 mill max might be an option.
Brandon Tanev- like Gourde, energy player, but will be 34 next year in December, so it would need to be a short contract.
Anthony Mantha - if the Habs strike out everywhere, then sign him cheap. He was decent for the Flames to start the season. Now he's done for the year, so another 1 year, 1 mill contract.
Jordan Greenway - Would be a nice bottom 6 add. Would hope for him.
Luke Kunin - would be a nice 4th like addition.
Tanner Jeannot - would be a nice bottom 6 add.
Trent Fredric - would be a solid middle 6 add.
Nicolas Hague - I just want him because I wanted the Habs to draft him. There's no logical reason for him.
Nick Bjugstad - similar Hague, I wanted the Habs to get him, but he's good on the dot and a capable 4th liner if Evans leaves/is traded away.
Klim Kostin- pretty tough guy, good 4th line/13th forward. He's RFA, but I imagine he won't be getting a QO. Would be a Russian on the team, too.
Nathan Bastian - 4th line centre physical, but got worked by a dwarf in Lomberg.
Christian Fischer - if the Habs miss out on everyone and everything an ok 4th liner/13th forward.
Mathieu Olivier - A must sign. Probably the heavyweight in the league, good PKer and has skill to play.
Brett Leason - Nothing happens sign him and give him some top 6 minutes and see what happens. Though could be a decent bottom 6 player.
Drew O'Connor - give him some ice time and see what he can do potentially
Walker Duehr- sign for Laval, but he has good size and decent speed for a call up if need be
Julien Gauthier - good size and a nice shot, so a good player to play both leagues.
Wortherspoon and Arseneau re-signed.
Dylan McIlrath- if they can, sign him and that way Laval is more than covered for toughness. McIlrath can also be solid in a few games here and there in the NHL and be a solid contributor in the AHL, too.
Justin Brazeau - would sign him for the Habs, but I'm a home for him.
Justin Bailey - mostly AHLer with size and skill there and can cover for a call up here and there
Riley Tufte - like Bailey, but I'd be more willing to see him get a chance with decent NHL lineages and maybe some games to see what he can do.
Derrick Pouliot if Mailloux makes the Habs, or is traded.
Obviously not all of them, but there's some nice options to fill needs/replace players for the Habs in the off season..