The day that most defined Mike Milbury's NY Islanders tumultuous tenure

Rick DiPietro...
Rick DiPietro... / Nhan Chu/GettyImages

On June 24th, 2000, the New York Islanders and GM Mike Milbury made NHL history by drafting Boston University goaltender Rick DiPietro with the first overall pick.

That wasn't all he did.

Three trades and two Top-5 picks have led to over two decades of second-guessing. It's the day that has most symbolized and defined Milbury's tumultuous tenure as Isles GM more than any other.

His moves were bold and brash, as most were. You could always count on Milbury making the unconventional move, the type that, if it worked out, would make him look smarter than everyone else. When it inevitably didn't, he spoke with enough confidence about the next one to make you believe he knew what he was doing - at least, he convinced ownership that was the case.

"Goaltending being the most important position in the sport, we're hanging a lot of our reputations on this kid. It's gutsy, maybe crazy, but at least we have the courage of our convictions and we think he's a very special player."

Mike Milbury at the 2000 NHL Draft

Preceding the drafting of DiPietro, Milbury traded future Hall-of-Famer Roberto Luongo, widely regarded as the top goalie prospect in the league, along with Olli Jokinen, acquired from Los Angeles as the centerpiece of the Zigmund Palffy trade for up and coming forwards Mark Parrish and Oleg Kvasha. As the deal raised eyebrows around the league, Milbury viewed it as a way to improve their forward depth while still having a generational goalie prospect.

""We didn't get chopped liver in return. We filled the holes we wanted to fill. It's a win-win day for us. We're doing a little dance over at the Islanders' table.""

Milbury in the New York Times

Luongo wasn't the only goaltender he traded on this day. Kevin Weekes, acquired in one of Milbury's better moves with Dave Schatchard and Bill Muckalt from Vancouver in a deal for Felix Potvin, was moved to Tampa Bay in a package with prospect D Kristian Kudroc that gave the Isles the fifth pick in the draft. Milbury selected power forward Raffi Torres. In 31 career games on Long Island, Torres failed to score a goal and was shipped to Edmonton with Brad Isbister for Janne Niinimaa and a second-round pick. Torres scored 20 goals in his first season with the Oilers.

Kevin Weekes
New York Islanders vs New Jersey Devils / Jamie Squire/GettyImages

The final move was trading Eric Brewer, another of the organization's top defensive prospects, and forward Josh Green, another piece acquired in the Palffy trade to Edmonton for established defenseman and former 1992 No. 1 overall pick Roman Hamrlik.

Did Milbury lose every trade on this day? No.

Hamrlik had four very productive seasons with the Isles and was part of the team's renaissance during the 2001-02 season. Kudroc played only 26 games, and while Weekes was always a serviceable NHL goaltender, he wasn't a clear No. 1 throughout his career. Torres scored 137 career goals, ninth best in that draft class, though none happened for the Isles.

This was typical of Milbury's time with the Islanders. There were bits and pieces of really good and shrewd moves, but they were mixed in with trades and decisions that overshadowed them all. On that day, fans gathered at a draft party on Long Island and reportedly booed when the Luongo trade was made, perplexing them as it did many around the NHL.

"I don't think the [reaction to the deals] was warm and fuzzy," Milbury said in The Washington Post. "But I don't think you make trades based on what the reaction is."

Maybe he should've; things could have turned out better for him and the organization.