The Toronto Maple Leafs have to trade Easton Cowan if they want to win the Stanley Cup.
Easton Cowan is the Toronto Maple Leafs Top Prospect, and it would very much suck to trade him, but unfortunately, given the team's win-now mandate, the age of their current best players, the team's needs and their assets to acquire what they need, they are going to have to bite the bullet and trade him.
The only other option is to trade Matthew Knies, and at least trading Cowan wouldn't hurt the current team's chances of winning the Stanley Cup.
For the record, I hate even saying this, but if you can see another way to get the things the Leafs need to win this year, and if you can convince me this year isn't going to represent the very peak of their Cup chances, then I'll take it back.
But I don't think you can do that.
Easton Cowan is the Toronto Maple Leafs best Trade Chip
The Leafs don't have a first-rounder next year, and they have already traded five out of 14 possible picks in the next two seasons.
Their prospect group is weak in the sense that outside of Easton Cowan and Matthew Knies they don't have a single player that would bring back a big return. They are also limited with what they can do with their current roster, because Morgan Rielly, William Nylander, John Tavares and Mitch Marner all have full no-movement clauses.
The Leafs need to get a 3C, which they could probably do without too much trouble. They can try out Domi, Holmberg, Tavares or maybe Roni Hirvonen or Fraser Minten, and then if nothing works they can send a 2nd rounder to some team about to miss the playoffs and get themselves a servicable top-nine guy for the playoffs.
Getting an elite 3C or getting that long-sought-after number-one defenseman is a different story. For either of those pieces, they are going to need to make Easton Cowan a part of a package that probably also includes a first-rounder.
With this package in hand, they should attempt to acquire Mortiz Seider, Zach Werenski or Simon Nemec. I don't know what the Leafs actually plan to do, but those are the guys I would try for. I think the defenseman is far more important than the forward if they want to win the Cup - if everyone on the Leafs current blue-line was pushed down one slot on the depth chart, they'd have the best blue-line in hockey.
Unfortunately, I just don't see a way for the Leafs to improve their roster enough to win now without trading Cowan. He is literally their only good trade chip, and thus their best one.