No. 1: William Nylander gets traded
He may be one of the NHL’s best offensive players at the moment, but if the Leafs lose in the First Round, it’ll probably be because Nylander was afraid to go into the corner or was beaten on a puck battle.
If Toronto loses, the team can’t bring back the same core-four forwards and the only logical choice would be to trade Nylander. Based on his contract, he’s the easiest player to move and could fetch a huge return.
Although you may want to move John Tavares instead, he has a no-trade-clause so that’s not going to happen. As for Auston Matthews and Mitch Marner, that would be like trading Michael Jordan and Scottie Pippen in their prime, so that would be a terrible decision.
A Nylander trade would not only open up $7M in cap-space but it make this team look a lot different, depending on where they used his money. Maybe they search for a number-one defenseman or goaltender, or instead find another forward who plays a different style.
Either way, if the Leafs lose, Nylander is gone.