Doc, how will the Leafs get Pitt's 1st rounder from the Pens if the Pens fail to make the playoffs?
If the Penguins fail to make the playoffs this season, they keep their 2016 first-round pick and the Leafs then get their 2017 first-rounder. But if Pittsburgh misses the playoffs both this season and the next, then all Toronto would get is their 2nd-rounder obtained in the Daniel Winnik trade at the end of last season.
In other words, if the Penguins either miss the playoffs this season or next, then the Leafs are okay and will get a 1st-round pick. That first-round pick is lottery-protected. So as long as Pittsburgh misses the playoffs, they'll get to keep their pick.