Leafs

I don't see either trade happening. Ronnie Francis isn't giving up on Shane Wright this early and certainly not for rental Willie. Why is Carolina retaining on Pesce? LOL

He's already playing on one of the best bargain contracts in the NHL.

It's not far away from Pesce, but it's a little light. Robertson has almost no value due to his injuries. Lilly + 1st is a good starting point though. If you need the retention like you do here, it's going to cost a lot more though, so you may need to find a way to shift 2 million more before trying to make a deal like this.

Retention can be moved to a 3rd team. Leafs would need it to make the deals work. Robertson + to a 3rd team for 1 year retention.

This trade doesn't make any sense for the Leafs. Pesce is a good player, but that doesn't make him a good trade candidate. Firstly, I think you're underestimating how inefficient that next Pesce contract is going to be. You might like the player he is now, but his underlying numbers suggest he has regressed a little bit over the past 3 seasons. He's still a very good top-4 defender, but are you really willing to extend a player at a massive number into his 36/37 year old season? And that's not even considering all the assets you are giving up for him.

Timothy Liljegren on the other hand is entering the prime of his career and will surely be a solid two-way top-4 defenceman for years to come. On top of that, his next contract will be SIGNIFICANTLY more affordable than Pesce's and it will likely be for his best seasons rather than Pesce's worst.

Brutally bad for Seattle, trading for one year of Nylander.
Brutally bad for the Leafs trading for one year of Pesce.
And please no silly extension talk.