You’re just sending a bag of pucks and draft picks to Chicago, they decline. Canucks might accept but I don’t really want Boeser, he’s not gonna fit with the leafs. He has a better chance playing good possibly with the wild or the kings maybe. I’d rather keep holl, dubas probably won’t trade holl either.
Horrible trades tbh

Sorry the only thing of true interest is 2023 1st round pick and maybe Robertson. Nothing in that deal helps the Hawks long term, just a bunch of cap clearing for Leafs, and that costs. You included them to get more cap, that costs my friend.

Canucks should split the twonul and get better returns individually

If Chicago wanted to be good/decent... they would have kept Dach and Debrincat. They are TRYING to bottom out and al they want are picks. the y get picks in the deal and they get additional assets in Kerfoot and Engvall who are on expiring deals they can flip for even MORE picks!

Don't see Boeser providing a better return on his own than Nylander. And next year Boeser would be playing with Matthews as he would slide up after Kane vacates the top line RW spot. JT and Marner should stay together. Best thing for JT and the team's scoring depth to keep Matthews and Marner separated.

Boeser has lots to prove - but his lower then Nylander salary and longer term is definitely something the Leafs should take advantage of while they wait for the salary cap to increase as significantly as it should.

CHI declines.

This is a great way to turn the team from a top 3 defensive team to a bottom 3rd team. Hard pass on all of this

Marginally better this year at a big expense for the future.
Four meh players this year.......Kane, Domi, Boesner and Gudas and the good Horvat for the meh Engvall, Kerfoot, Holl, (possibly needed Simmons, Kallagren, Robertson) and the good Nylander plus two first and second. Plus the Leafs can saddled with the poor Boesner contract for two full seasons.
I would suggest that any short term rental trades by based on the players playing value NOW, not what it was in previous seasons. Also check how players perform at full strength, as many players on poor teams can pad their stats on the PP, and they certainly wouldn't getting the same PP time with the Leafs.
No logic in thinking five new player can fit in seamlessly into their new club in less than half a season.

I don't know why some Leaf fans hate their own and think some middling players from other players (this year edition) are a help to the Leafs.

Those types generally have all their hockey knowledge from playing video games.

I love Leafs fans on here. All of them are so similar - lets send a bunch of players (quantity) vs any real important players (quality) that a team would actually want / see value in

Cracks me up every time

Engvall, Kallgren, Simmonds, and Kerfoot have negligible trade value.

Robertson isn't that great and a Leafs first isn't worth that much.

Chicago declines, and the Vancouver trade is criminally terrible for Toronto.

Kane + Domi >>>> Engvall + Kerfoot (both can be flipped for mid to late round picks by CHI) + (Simmonds is only in for cap purposes) + (Robertson + Khalgren + 1st + 2nd even things out and covers 50% salary retention)

Horvat < Nylander (Boeser tips the scales in the Leafs favour some (allot if the Leaf's can sign Horvat to an extension equal or close to Nylander's current $7m cost - 1st and 3rd to balance the scales out talent wise and covers 50% salary retention)

Gudas = Holl (Holl scares NOBODY - Gudas puts the fear of god into opposing wingers - even at this stage of his career - and is a MUCH better penalty killer/defensive net front presence - makes opposing wingers pay a price for getting close to the G - 2023 3rd for 2025 2nd covers the small salary retention)

How am I wrong in this analysis? Please someone "educate me" on my apparent "video game" knowledge/perspective on the sport.

Everyone’s entitled to an opinion, and your rationale is well thought out.
I would prefer to keep Kerfoot & Engvall - their defensive metrics are fantastic. Kane & Domi are not the types of players we need, imo.
Why do you say Gudas is better at PK than Holl? I think Holl has played well but I could be convinced to bump him down to 7th d for playoffs but Gudas is just not very good, physical play aside