Winnipeg has a surplus of RHD, I’d be curious to see if something around Trouba or Myers is something of interest for Toronto. Winnipeg could opt to use Nylander as their second line center.
It's the lack of term for Trouba or Myers, so the Jets would have to add. Both teams are at the cap limit next year (Jets are over it), so that a consideration. Other teams probably don't overpay Nylander any more than the Leafs do, which I think is the biggest obstacle in any trade. Nylander not signed means no trade. Nylander signed to a fair contract, Leafs keep him.