Few teams have historically been run as poorly as the Toronto Maple Leafs.
The Toronto Maple Leafs have seen many players come and go through the years.
It always stings when someone they had within the organization develops well beyond expectations, only it’s with another franchise.
This has been the case too many times in the organization’s very long history. However, these are usually well known moves. For example, when the Leafs bet on Andrew Raycroft and Justin Pogge to be the future starters in goal, they gave up a young prospect named Tukka Rask who ended up carrying the Boston Bruins for 15 years.
Or when Boston used the draft picks they received for Phil Kessel to draft Tyler Seguin and Dougie Hamilton. Seguin was as good as Kessel, but Dougie Hamilton went on to become one of, if not the best defenseman of his generation.
Lopsided trades like that one live in infamy.
Those well publicized and often discussed transactions aren’t the focus here.
There have been moves made that haven’t received the same level of press. There are the Leafs disaster transactions that have gone under the radar.