Mike Milbury's tenure as general manager of the New York Islanders is widely regarded as one of the most damaging in NHL history. From 1995 to 2006, "Mad Mike," as he was known, made a series of questionable trades, draft decisions, and signings that set the franchise back for years. Here's a look at ten of the worst moves that defined his disastrous reign:

1. The Alexei Yashin Trade: In 2001, Milbury sent Zdeno Chara, Bill Muckalt, and the second overall pick in the 2001 NHL Draft (which became Jason Spezza) to the Ottawa Senators for Alexei Yashin. While Yashin had some productive seasons with the Islanders, his large contract and inconsistent performance became a burden on the team. Chara, on the other hand, went on to become a perennial All-Star and Stanley Cup champion, while Spezza had a long and successful career. This trade is considered by many to be the worst in Islanders history.

2. Trading Roberto Luongo and Olli Jokinen for next to nothing: In 2000, Milbury traded star goaltender Roberto Luongo and forward Olli Jokinen to the Florida Panthers in exchange for forwards Mark Parrish and Oleg Kvasha. Luongo became one of the league's best goaltenders, while Jokinen was a solid offensive contributor. Parrish had a few good seasons with the Islanders, but Kvasha was largely ineffective. Milbury's assessment that he "didn't get chopped liver in return" and that it was a "win-win day" has become a source of mockery.

3. Drafting Rick DiPietro First Overall: With the first overall pick in the 2000 NHL Entry Draft, Milbury selected goaltender Rick DiPietro. While DiPietro had some potential, many believed that the Islanders should have drafted Dany Heatley or Marian Gaborik instead.

4. The Rick DiPietro Contract: Perhaps even more egregious than drafting DiPietro was the 15-year, $67.5 million contract extension Milbury awarded him in 2006. DiPietro's career was plagued by injuries, and he ultimately became one of the biggest contract busts in NHL history.

5. Trading Bryan McCabe and Todd Bertuzzi for Trevor Linden: In 1998, Milbury traded Bryan McCabe, Todd Bertuzzi, and a third-round pick to the Vancouver Canucks for Trevor Linden. McCabe and Bertuzzi went on to have long and productive careers, while Linden's impact on the Islanders was minimal.

6. Trading Ziggy Palffy: Milbury traded Ziggy Palffy, Bryan Smolinski, Marc Cousineau, and a 1999 fourth-round pick to the Los Angeles Kings for Olli Jokinen, Mathieu Biron, Josh Green, and a 1999 first-round pick. Palffy was a consistent scorer, and the trade did not yield commensurate value for the Islanders.

7. Trading Tommy Salo: Milbury traded goaltender Tommy Salo to the Edmonton Oilers for Mats Lindgren and an eighth-round pick in 1999. Salo was a promising young goaltender, and the return for him was underwhelming.

8. Trading Darius Kasparaitis: Milbury traded Darius Kasparaitis and Andreas Johansson to the Pittsburgh Penguins for Bryan Smolinski in 1996. Kasparaitis was a solid defensive defenseman, and Smolinski's tenure with the Islanders was unremarkable.

9. Firing coach Al Arbour, then hiring him again Al Arbour coached the Islanders to four Stanley Cups in the 1980s. Milbury fired Arbour twice then rehired him.

10. Controversial Comments as a Broadcaster: Even after his time as GM, Milbury remained a controversial figure due to his inflammatory comments as a broadcaster.

Mike Milbury's moves as general manager of the New York Islanders had a devastating impact on the franchise. His poor judgment in trades, drafts, and signings left the team in a state of perpetual rebuilding for many years. While he may have been trying to shake things up and bring success to the Islanders, his decisions ultimately backfired and cemented his legacy as one of the worst GMs in NHL history.