Sure... lets trade away 22 year old Nylander with years left of team control, who had back to back 61 point season, for a goalie we waived earlier in the year and 30 year old wayne simmonds who never in his career has surpassed nylanders 61 points and is about to hit a steep decline into the twilight of his career. Hes not going anywhere but downhill. That would be worse than the Taylor hall trade. As for the other trade. I'd rather just resign Gardiner.

I just don't want to lose Nylander for nothing... and we waived Pickard not because we wanted to.
I think Simmonds has some left in the tank. If signed now, he could be a cheap 2nd/3rd line option (and would provide some muscles and experience)

Vatanen is signed for 2 more years below 5M.

With all this, it could clear the path for signing Marner - Matthews - Kapanen.

Anyway, that was my thinking.

Actually we did waive Pickard because we wanted to. We lost him to waiver which we didn't want to do. What makes you think Wayne Simmonds will be a cheap option? He's UFA after this year. Think of a Max Pacioretty type deal, maybe more since he had the luxery of signing with a no state tax team. Similar Age and production over the last several years (30G/30A) approximately. A long term Wayne Simmonds trade would handicap us for a decade. Think of the Lucic deal. 30 years old, a shadow of his former self and causing huge cap complications for the next 5 or so years. Signing simmonds would be a huge net negative on our cap troubles. If kyle Dubas was dumb enough to do this the team deserves another decade of failure.

What makes you think we will lose Nylander for nothing? He literally can't sign with any other team without receiving rfa compensation (which would be worlds better than your proposal), or we trade him for an equal or greater value. I would rather let Nylander sit for the entire year than take on the anchor that Simmonds will likely be for the next half decade.

Vatanen is signed for 1 year longer than Jake Gardiner. I'd rather have Gardiner than trade away leivo and rosen. This Trade isn't as atrocious as your other proposal, but still not great.

What is this madness about losing Nylander for nothing? He's under Leafs control for five years including this year. Jersey loses on that deal just because of term (like the Leafs do on the Philly deal).

OK...OK... I am having a hard time answering these comments except maybe on Gardiner who will ask for a whole lot. (You know that moment when your GPS tells you to turn right... and you still go left?)

I'll try something else.