Per Elliotte Friedman, sounds like there's no love lost between Nylander/his reps and Kyle Dubas...today Nylander's agent apparently slammed Dubas as an inexperienced stats geek and blamed him for the contract stalemate. So a trade is a very real possibility, but as others have pointed out Ottawa likely either doesn't have or isn't willing to give up the pieces Toronto would want.
Nylander leaving money on the table makes no sense.
The argument a lot of Leaf fans make is that if he is traded, he'll probably go to a worse team, and he has a chance to be part of a powerhouse on the East for several years, which might be true.
But consider that he's 4th banana up front to a team that has Matthews, Marner, Tavares, and also to a lesser extent Kadri.
I can see how Nylander looks at the situation and sees that if he leaves money on the table, he has no real assurance he will be kept long term. The Leafs D is sub par, and he's their most logical trade chip to fix that. Maybe not right now, but if the Leafs fail in the post season, 1, 2, 3 years from now, there's no way they don't explore a Jones for Johansen type swap to fix their backend.
So he leaves money on the table only to open himself up to being dealt. Or he can force a trade and sign for 8*8 somewhere that he'll be the guy.
I also think there's more pressure for Toronto to resolve this than for Nylander. Nylander is losing money in the short term, but even if he holds out for a year, if it results in an 8M+ AAV, he makes back that lost cash and then some compared to signing a 6.5M type AAV contract now. Expectations from fans and media are for Toronto to go deep. A 1st or soft 2nd round exit with Nylander sitting out would get the team crucified.
I also think there's a different dynamic because Nylander's a dad was a player and their family probably isn't starving. I could be wrong, but I fully expect Nylander's camp to win this, whether that is by a trade, Toronto paying him, or Nylander sitting out the season and eventually getting paid or traded.
