Personally, I would have traded him the year they signed Tavares, the second this whole contract thing started. He doesn't hold out for half the season and show up playing at half his potential, the Leafs show that they aren't going to cater to whatever the players demand, and their salary is not out of control.
But really, Tre should have traded Nylander before his NMC kicked in. He's a luxury, and now he's an insanely expensive luxury. And now the Leafs are starting at the exact situation I was afraid they'd end up in when this whole shit started; the very real possibility they're rebuilding in four years with a 35+ $11 million Nylander and NOTHING ELSE. Remember the end of the Sundin years? Picture that, only with a worse player overall.