25 Years Later: Remembering the NY Islanders and Rick DiPietro draft gamble

June 24, 2000. If you were a New York Islanders fan back then, you remember exactly where you were. It was the day when GM Mike Milbury went all-in on Rick DiPietro, making him the first goalie drafted first overall. Twenty-five years later, we’re still talking about it—for better or worse.

Let’s set the scene. The Islanders had two promising young players: Roberto Luongo, drafted 4th overall in 1997, already showing flashes of elite-level goaltending, and Olli Jokinen, a skilled forward with upside. But Milbury had a vision—maybe “obsession” is a better word. He wanted DiPietro. A brash, confident kid out of Boston University who lit up interviews with charisma. He was cocky, he was self-assured, just like Milbury.

To make room for his “franchise goalie,” Milbury dealt Luongo and Jokinen to Florida that morning. Islanders fans were stunned. Two of their top prospects were gone in the blink of an eye. The Isles also moved backup goaltender Kevin Weekes to the Tampa Bay Lightning earlier in the day. "We're hanging a lot of our reputations on this kid," Milbury said of DiPietro. "It's gutsy, it may be crazy, but at least we have the courage of our convictions."

“Even though I knew, it was still surreal,” DiPietro said to NewYorkIslanders.com in a recent feature. “They can tell you, but until you hear your name called and you walk up there and get the jersey… it’s something where I didn’t really believe it until it actually happened. Once they said my name, I thought about all the work and all the sacrifices my parents and brother made. To finally be on that stage as the first-overall pick, it’s a day you’ll never forget.”

He showed promise. He had the confidence. But then came the injuries… and that contract. Fifteen years. FIFTEEN. It became a punchline across the league. Looking back now, the DiPietro pick is a time capsule. It’s the Milbury era in a nutshell: bold, chaotic, emotional. It’s easy to shake our heads now, but at the time, it felt like we were watching the start of something.

Twenty-five years later, it’s not the fairy tale we, especially, hoped for—but it’s a chapter Islanders fans will never forget as long as the team is still paying DiPietro (it's until 2029) and beyond.