Toronto fans won't like to spend that draft capital but with Matthews deal expiring in 2 years time, Campbell up for a raise (Or searching for a new goalie tandem?) and Reilly's extension kicking in next year I think this year is the year for the Leafs need to make the extra push. I wouldn't even mind if Toronto asks for a top 20 protection on the first rounder, the unprotected next year would be good enough to warrant the gamble.
Division rival adds the extra pick.

Chiarot even doe isn't elegant is a minute muncher, heavy hitter, PK guy that can help a team go further in the playoffs. He's punishing guys (Remember how Matthews was covered in front of the net in last year's playoffs?) and has low key very good skating agility with the puck, he's the guy you want to acquiring to boost your top 4. Great PDO every playoff year he played, 66% defensive zone starts and block shots.

Seravalli said there is at least 3 teams in a Lehkonen derby, likely the Rangers, Avalanches (Known to be roving around Lehky for awhile) and a third mystery team. At this time I feel like NY has more on the table to offer, Colorado's best pick this year is a third rounder and their prospects are either with the team now or not down the needs of Montreal, only one's of interest could be Olausson or Ranta. With NY you have access to a much larger pool of picks and a bigger spectrum of prospects, they could either send a pair of second round picks or a mix with a good prospect like in this case. Players like Cuylle, Barron and Kravtsov could be on Montreal's radar.

No need to explain, he does everything good and can be QO'd next year if they like him.

Finish HERE: Now what could Montreal realistically ask for him, to me this trade only happens if he's requesting not to be kept in a rebuild phase otherwise I likely try to keep him at least until we know if Price will ever play a game again. First round pick is unlikely to me but if you offer me something around what Lehkonen could get I'd listen. Would start with the better of Detroit's second rounder which would likely be in the high forty's, then you look around their non rostered prospect and after goign through the plethora of LD's I see Berggren. Very good first year in the AHL, signed and plenty of potential, a good playmaking winger that will likely be a middle six winger with upside. With wingers like Raymond, Bert, Vrana, Nammy, Fabbri, Zadina and plenty of draft capital for more it's a move Detroit can afford to do. Adding Greiss cause Montreal needs warm bodies if Allen goes to be with Montembeault while Primeau finishes his AHL 'career'. Taking Greiss is the difference maker between getting the better second round pick instead of the lower.
On Berggren's value, I'm not completely sure of it but I've seen trades made for Strome and Branstrom's swap so I simply tag a second round pick value on him, any slight off measure could be taken care off by picks or salary retention.

Start HERE: I might surprise some here but I'm going off the board on this one and selecting the darkhorse Detroit. Holland basically doesn't want to spend a penny for a starting goalie, Vanecek -2.7 goals saved above expected is a big reason why he’s only won four of 13 starts and Adin Hill hasn't met expectations this year but I'm choosing Detroit for this one. The Wings are on the back end of their reset/rebuild with still a plethora of pick and prospects they could use to acquire players. Lately Yzerman hasn't been afraid to spend to go get who he wanted trading up for Cossa at 15OA, trading up for Buium at 36OA and trading for roster players like Leddy and Nedel so if the price is right I wouldn't be surprised to see him move while his team's pushing for a playoff spot. Greiss' been gross this year while Alex's been keeping the good work, I think Nedel needs a good veteran backup that can take games regularly when needed.

A team looking to get a depth defenseman just like it happens every year (Merrill, Gustafson, etc). FLA is more of a placeholder but could also be in the hunt for depth. Pure rental.

Waiver or straight to Laval buddy.