A Promising Career Cut Short

For years, Rick DiPietro has been considered one of the biggest draft busts of all time, and it’s hard to argue against it. Selected first overall in 2000 by the New York Islanders, he was immediately hailed as the team’s goalie of the future and around whom they would build their franchise. Yet 13 seasons after he was drafted, the team bought him out of a deal that they will be paying until 2028-29. It’s a black mark on the organization, there’s no question about that, but very little of what happened is DiPietro’s fault.

Not only did injuries completely derail his career, but DiPietro was never put into a position to succeed. Either he was thrown to the wolves on a weak roster created by a management group that failed to identify and acquire talented players, or he was buried by an organization that was ashamed that they selected him in the first place. Not even the greatest goalies of all time could have rectified the Islanders of the early 2000s. While his tenure is unquestionably disappointing, he shouldn’t be considered a draft bust.

Mike Milbury’s Mismanagement

Mike Milbury has gone down as one of the worst general managers in NHL history. From 1995-2006, he led the Islanders to just three playoff berths and five playoff wins and finished in the league’s top 10 just once, coming in eighth place in 2001-02. His impact arguably caused the franchise to struggle for another decade after his departure.

But in 1999-00, Milbury didn’t have that reputation yet. Sure, he was seen as an overconfident manager, but that’s what the Islanders needed to get out of their four-year playoff drought. So, when a young, hot-shot goalie decided to enter the 2000 Draft rather than wait for 2001, giving up his college eligibility, Milbury saw a chance to give his franchise a huge boost. Not only would he be making history by selecting a goalie first overall for the first time in modern history, but he would also solidify the team’s shaky crease.

DiPietro was far from a bad pick, even at first overall. In his first season with Boston College, he won Hockey East’s Rookie of the Year, New England’s Most Valuable Player, and also was named the best goaltender at the 2000 World Juniors while playing with Team USA. He was labelled as a future all-star and certainly…