8. Islanders Use Their 2000 First Pick On Rick DiPietro

Dumbass Move By: Mike Milbury and the New York Islanders
Date: 6/24/2000
When Mike Milbury made Rick DiPietro the first goaltender ever drafted first overall in NHL history, it only added to the infamous legend of "Mad Mike." With that pick, Milbury missed out on stars such as Dany Heatley, Marian Gaborik, Scott Hartnell, and Ilya Bryzgalov for a guy that is now referred to as "Rickety" DiPiertro (a jab at how injury prone he has been). He also traded away another future All-Star in Roberto Luongo in the process. All that for someone who's played in just 39 games over the last three seasons. SMH. Seriously, by stepping down as GM, Milbury made his best decision when thinking about the Islanders' future.