3. Not Trading William Nylander At His Absolute Peak
William Nylander is a special player and one of my favorite Toronto Maple Leafs of all time.
The fan in me is happy that he re-signed and will likely play his whole career on my favorite team. Like Morgan Rielly, this makes me extremely happy.
But also like Morgan Rielly, the cold analytical part of my brain knows that signing him was probably a mistake.
Nylander will never be better than he is right now, and the smart play was to do a sign-and-trade to bring in the kind of elite defenseman or goalie that you can't really get without drafting or making a major Trade.
Nylander for Noah Dobson? Nylander for Juuse Saros? Something like that would have helped a lot more than re-signing your third best offensive player.
Again, I love Nylander and I'm happy he's here. But when the guy is absolutely peaking at the perfect time, you've got to trade him for a younger player who plays a position you need.
Then again, maybe the Leafs will prove me wrong by winning the Stanley Cup with the best forward group in hockey but also the worst blue-line and goalie group of any contender.