Ranking the NY Islanders Ten Top-10 Draft Picks of the 1990's

After all the success of the NY Islanders in the 80s, the 90s were nearly the opposite. The team struggled on and off the ice, whether making the playoffs only three times in the decade or having the team sold to a con artist who could barely afford season tickets.

In 1995, the organization and the fan base endured one of the darkest times in the franchises history, as ownership elected to change the famous Islanders logo and colors for a new wave (pun intended) brighter color scheme with a fisherman logo.

If there's one positive about finishing near the bottom of the standings year after year, it's the draft picks that come with it. Picking high in the draft for a decade straight, the Isles were bound to hit gold at least once, right? The odds were in their favor of finding a modern-day Pat LaFontaine or Denis Potvin, right?

The Isles made ten top-10 selections from 1990-1999. Some were duds and some went on to have solid NHL careers, with one inducted into the Hall of Fame.

Here's how we rank the ten top-10 draft picks made by the Islanders in the 1990s. These players are ranked on how their NHL careers panned out, not just their time with the Islanders:

6. Mike Rupp (9th Overall, 1998)

The story of Mike Rupp being drafted by the Islanders can leave you saying, "That would only happen to the Islanders." Rupp was never a big point producer leading up to the 1998 draft, but the Isles selected him ninth overall nonetheless.

Rupp remained unsigned while continuing his junior career, electing to re-enter the draft rather than sign with the Islanders. He was taken 76th overall by the New Jersey Devils in the 2000 NHL Draft, never even seeing the practice rink on Long Island. Rupp appeared in 610 games over 14 NHL seasons and scored the Stanley Cup-clinching goal for the Devils in 2003.

5. JP Dumont (3rd Overall, 1996)

Another high draft choice for the Islanders and another player to never suit up for them. JP Dumont was drafted out of Val-d'Or of the QMJHL, racking up 105 points during his draft-eligible season. Dumont elected to return to Val-d'Or for two more seasons playing out the remainder of his eligibility, still without a contract from the Islanders. Islanders GM Mike Millbury was unwilling to meet Dumont's contract demands as the team was down to their last day to sign the third overall pick before he'd re-enter the draft. The two sides came to terms on a three-year $2.6M contract before shipping him off to the Chicago Blackhawks in exchange for Dmitri Nabokov.

Dumont never became the player he was in juniors but managed 523 points over 822 games. His best season came with the Nashville Predators in 2007-08, accruing 72 points (29 goals, 43 assists)

4. Tim Connolly (5th Overall, 1999)

As the player sent with Pyatt to Buffalo in a deal that returned Peca to the Islanders, Tim Connolly spent two seasons on Long Island, scoring 24 goals with 51 helpers while missing just one game.

During Connolly's third season with Buffalo, injuries began to plague his career. The once scintillating playmaker was consistently hurt, facing constant bouts with concussion-related issues. Following the 2012 season with the Toronto Maple Leafs, Connolly was sent down the minors, appearing in just 28 games with the Toronto Marlies before calling it a career and retiring at 31.

Connolly managed 432 points (131 goals, 300 assists) in 697 games, during a promising career derailed by injuries.

3. Wade Redden (2nd Overall, 1995)

Another instance of a top-10 pick never lacing up for the Islanders, but this one worked out for the Isles.

Wade Redden was taken second overall, behind the top pick of the Ottawa Senators, Bryan Berard. Berard believed he was ready to contribute in the NHL immediately, but the Sens thought otherwise, returning him to Detroit, to continue in junior hockey. Berard, unhappy that he wasn't part of the Senators plans for the 1995-96 season, demanded a trade.

The Isles sent Redden to Ottawa as the pivotal piece that landed Berard on Long Island. Redden went on to have a phenomenal career, playing in 1,023 games over 15 seasons, recording 457 points. Though he never played for the Isles, he's part of Islanders history as Berard became one of the team's top players of the 90s.

2. Darius Kasparaitis (5th Overall, 1992)

One of the names synonymous with the Islanders in the 90s, Darius Kasparaitis, brought grit every night for teams that struggled to accumulate points. Kasparaitis stepped into the lineup as an 18-year-old, unwilling to back down from the biggest of opponents.

Kasparaitis's career was played across 16 seasons and four teams, scoring 163 points as a defenseman who could wear down the most formidable opponents. He spent just five seasons with the Islanders, traded a month into the 1996 season to the Penguins in exchange for Bryan Smolinski.

Since his retirement, Kasparaitis has been around the organization more often following the construction of UBS Arena. He'll always remain a fan favorite among the Islander faithful.

1. Roberto Luongo (4th Overall, 1997)

One of the trades the Islanders and Mike Millbury wish they could have back. After playing just 24 games for the Islanders, Millbury shipped off what would become one of the best goaltenders in NHL history, Roberto Luongo, to draft Rick DiPietro.

Luongo and Olli Jokinen were shipped to the Florida Panthers for Mark Parrish and Oleg Kvasha before the 2000 NHL Draft, as the trade became one of regret and will haunt the Islanders, wondering what could have been.

Luongo played in 1,044 regular season games, winning 489 of those, making him the fourth-most winning goaltender in NHL history. He was inducted into the Hockey Hall of Fame in 2022, most known for his time with the Panthers and Vancouver Canucks.