6. Eric Lindros and Scott Niedermeyer
The funniest thing about the Toronto Maple Leafs might just be that this isn't number-one on the list, but just the half-way point.
Once upon a time, the Leafs were a brutally bad team set to draft first overall and select the best player to enter the NHL in a decade.
The reward for being the worst team of the 80s was going to be the glory of building a team around the most exciting player to enter the NHL since Wayne Gretzky. Eric Lindros was not only a new kind of NHL player - a huge monster who could also skate and score - but he actually ended up living up to the enormous hype.
And only because of the worst management in the history of pro sports did he fail to do so with the Toronto Maple Leafs.
Had the 1990-91 NHL season taken it's natural course, the Leafs very well could have finished in last place and selected Eric Lindros. It is a near certainty that they would have. The Leafs, however, had previously traded their 1991 draft pick, back in 1989, to the New Jersey Devils in exchange for Tom Kurvers.
The Leafs, as mentioned here by Steve Dangle, then went on to start the 1990-91 season 1-9-1, which should have been the best thing to ever happen. All that was left was to sell of parts and then draft Eric Lindros.
But since they didn't have their draft pick, they actually made moves to avoid finishing last. They traded prospects to the Nordiques in exchange for their best players to ensure it would happen.
The end result was that they "only" ended up giving away Scott Niedermayer instead of Eric Lindros. The only problem? Niedermayer was second only to Nik Lidstrom as the best defenseman of his generation and is now a hall of famer who arguably ended up having a better career than Lindros himself.
The fact that this isn't number-one on this list could in itself be an entry on the list.