3 way CGY-TOR-X team

I'll agree with non playoff teams should be trading their upcoming UFAs. But the Leafs have I believe 8 upcoming UFAs, do they all get traded? Of course not. There is no benefit to the Leafs this year if they are in a win mode to trade Nylander, unless they get immediate equal ice value back in a trade Gee, half the teams in the league in the won't be trading their upcoming UFAs.
And with that Nylander trade to the Canes......the Leafs get back two upcoming UFAs. Kinda defeats the purpose of trading Nylander because he's a UFA.

So your stance is to let Nylander walk at end of season for nothing? Or do you think they should extend him and have 4 guys making up over 40Mil of the cap?

Like so many, you use the "Let them walk". That is absolutely meaningless. The player has the choice of signing wherever he wants.
Now I believe the Leafs will make a fair offer to Nylander, but if he decides to sign elsewhere (for whatever reason) that's the nature of UFA.
This summer the Leafs had ROR, Accarili, Holl, Scheen "walk" as UFAs. But then they signed Bertuzzi, Domi, Klingberg who "walked" from other teams. Just an exchange of player...like "cap trade"
What makes Nylander so special? There are over 100 upcoming UFAs..
But to answer you question specifically. I really don't care if the Leafs resign Nylander (or Matthews/Bertuzzi/Domi/Klingberg/Brodie/ Giordano. Lafferty or Samsonov.....all UFAs next summer.
I don't think the Leafs (or any team)_ should overpay UFAs. I look at the Leafs will have 9 upcoming UFAs...but more importantly those 9 carry a cap currently of about 43m. As a Leaf fan hoping the GM spends that 43m wisely on whoever....some might be resigned, others won't.

Did you read the description? This was A) under the assumption that they won't be able to get Nylander resigned to a new contract before unrestricted free agency and B) Not necessarily for Carolina's players. I just used Carolina to get the point across. Also mentioned that Pesce would be resigned to the Leafs so they are getting a long term asset in the deal at a cheaper cap than what Nylander will cost them.

Secondly, I didn't say anything about having to trade all the pending UFA's. The players involved all happen to be pending UFA's but that was not the point of the post. The point was CGY has 3 UFA's that are probably not resigning. Tor has Nylander who they'll likely have to pay way too much for if they resign and would be better suited distributing that cap throughout the lineup more evenly. I used Carolina just because Pesce's name has been mentioned a few times but like i said, just used Carolina as the example 3rd team who may have what Toronto wants.

So basically making trades is pointless then? Lol Just let all pending UFA's walk and sign other teams UFA's.

Also I think we can all agree, Nylander is better than all the players mentioned that were let walk to free agency. They could potentially get better players in return in a trade then to simply let Nylander walk and sign someone else in free agency. There is no guarantee Toronto will be able to sign one of the players they pursue. At least not without overpaying, but then we're right back to the reasoning for NOT over paying for Nylander again.