This is going to be a lot faster written than my previous post, as my computer crashed 20s before posting it ... :[
Nylander
for
Weber, Toronto's 2018 2nd, Montreal's 2019 2nd, Michael McCarron.
Kadri, Kapanen, Liljegren and Toronto's 2019 2nd
for
Faulk, Pesce and Aho.
Zaitsev
for
Athanasiou, Islander's 2019 2nd.
Toronto's 2019 1st, Montreal's 2019 2nd
for
Zuccarello
Resign Komarov and Bozak.
Aho/Matthews/Marner
Hyman/Bozak/Zucc
Marleau/Athanasiou/Brown
Komarov/Leivo/McCarron
Rielly/Weber
Gardiner/Faulk
Pesce/Hainsey
For complete transparency, I am open to critique/conversation for all of the trades except the Montreal one. People on these boards criminally undervalue Weber due to his "atrocious contract" when in reality the Leafs would absolutely take him for the right price considering he fills such a needed role for the team. Weber has a LOT higher value than people give him credit for
The Leafs end up getting a lot better on the right side, and the addition of Pesce gives them a natural replacement for Gardiner. Aho serves to ultimately replace the loss of Nylander, and Marner could replace Bozak if there was a solid 2RW that the Leafs could bring in via trade.
Their offensive group definitely gets weaker short term, but they get cap flexibility around Zucc, Marleau, Komarov, Bozak and Gardiner's deals while ultimately retaining a very solid young core and getting infinitely better defensively.
The primary goal for any franchise is to win a Stanley Cup, at any cost --- and I am of the belief that this roster with the addition of a Top 6 RW at the Trade Deadline could contend for a cup.