Begin the teardown

*As per previous conditions agreed upon.

*Trade deadline deal*

I believe Florida's first option will be to add Jakob Chychrun form Arizona, but after seeing the asking price for him I think they'll look to a rental option and look at acquiring Chychrun in the off-season. Instead, I see them going hard after Chiarot and he seems to check a lot of boxes that they need. He's a big, defensive, physical, left handed defenceman that would slide into their top 4 immediately. After seeing how their playoffs series last season played out with Tampa, he seems to be the exact type of guy they should target and be all in for to put them over the top.

For Montreal, they begin the rebuild by dealing away a pending UFA. Quite a bit of interest has been reported in Chiarot so the reported price of at least a 1st round pick is definitely not out of the question. Since Florida doesn't have their 2022 1st round pick (and I see them being aggressive on Chiarot), I have 2 quality prospects as the main pet of the deal instead. Aleksi Heponiemi fits everything that Gorton said he wants his team to look like - fast and offensively skilled. Heponiemi was a former top prospect that hasn't cracked the NHL much yet but has produced well at every other level to hopefully be on track for a future top 6 option. In addition, a mobile two way defenceman like Evan Nause should be an interesting target as well. He's playing for Quebec in the QMJHL so Habs management had all the time they wanted to have a look at him. He's personally impressed me thus far in his career and I think he fits the type of style that Gorton is looking for. Montreal is also compensated with a 2023 4th round pick for retaining 50% in Chiarot's contract - I chose 2023 instead of 2022 due to the abundance of 3rd/4th round picks that Montreal currently owns in the 2022 draft and if they're rebuilding it's always good to add future picks.

To me this seems like a no brainer win-win deal.

*Trade deadline deal*

- Conditional 2022 2nd round pick (STL):
1. Montreal receives the highest of the 2nd round picks that New York currently owns (their own and St. Louis')


Rangers have been looking for complimentary players to add to their abundance of skilled ones. Artturi Lehkonen checks that off the list for them. He's defensively reliable and can chip in the odd goal or two as well. He's been compared to a similar Blake Coleman - so I've judged his value based on of Coleman's deal to Tampa Bay a few years ago however because Lehkonen is a pending UFA I've lowered it to a 2nd round pick and a top prospect. New York could also look to add some depth on defence in case of injures for a deep playoff run, which is where Kulak comes into play. He's reliable defensively and can play both sides if needed, as well as he'll be cheap at 50% retained salary.

For Montreal, again they look for future assets for their rebuild. Robertson is a young, solid two way defenceman who may even be able to jump into some regular NHL action as soon as next season. They continue to stock like draft picks over the course of the next 2 years for what are likely to be very deep drafts.

*Trade deadline deal*

- Conditional 2024 3rd round pick (CGY)
1. Montreal only receives this pick if Calgary advances to the Western Conference Finals in either the 2022 playoffs, 2023 playoffs, or 2024 playoffs and Toffoli plays on 50% of the playoff games in which Calgary reached the Conference Finals.

I think Toffoli is going to be the only Canadien with term on his contract that is moved at this years deadline. Everyone knows that goals are difficult to come by these days, and Toffoli fills the net a lot. I think they'll be a strong market for him the have any package start at either a top prospect/young NHL roster player and a 1st round pick, and Calgary definitely should/likely will be calling Montreal non-stop about Toffoli. The Flames have long been looking for a top 6 right handed scoring option and the familiarity of coach Daryl Sutter and Toffoli needs no new introduction. Toffoli could slide in immediately and likely not take long to adjust to the roster.

The Habs should be looking at getting a young NHL roster player as the primary part of a Toffoli deal, and Dubé fits what they need. He's being a solid two way game with some physicality and team control to his contract. He's a versatile player that can play anywhere in the lineup, however he's blocked in Calgary to really move up the lineup at all and could get his chance in Montreal to do so. Another interesting under the radar prospect for me is Jake Boltmann - someone I have Montreal adding to the rebuild. He could serve as a future #4 defenceman in the lineup, and he's a great leader - those types of players are key in a system for a rebuild. Habs also end off the deal with a guaranteed 1st round pick in 2022 and a 3rd round pick in 2024 to continue to stock pile the young assets for the future.