I am a bit a masochist, being a like long Leaf fan who has refused to turn of his TV during the worst of Leaf games (most of this season for instance) is a telling sign of that.
Being the bringer of self pain, and inspired by THIS post by Mr mf37 I decided to look at what might have been if the Leafs had not surrendered all of those needlessly spent picks and had some how miraculously finished in the same position every year and drafted the best available player in said round.
I call this the "Oh dear god why do I do this to myself" list of possible Leafs/ex Leafs
2000- Brad Boyes (1st rnd for Nolan)
2003- Corry Perry (1st rnd for Nolan)
2004 -Mike Green (1st rnd for Leetch)
2005 -Tukka Rask (1st rnd for Raycroft)
2007 - David Perron (1st rnd for Toskala)
I'm not even gonna go back any farther and look at the famous Luongo draft pick and all that because I would drive my head through my laptop.
I'm gonna go drink myself to death now.