In 2000, the New York Islanders possessed the first overall draft pick for the first time in  27 years. The Islanders decided to do something only done once before — draft a goalie with the first overall pick. That goalie was Rick DiPietro.

The last time the Islanders held the first overall pick was 1973 when the Islanders drafted future Islanders captain Denis Potvin. After selecting Potvin, the Islanders missed the playoffs just four times in the next 21 seasons. But after the 1994 season, the wheels fell off the bus. Following their fifth straight season without the postseason, the Islanders landed the first overall selection in 2000.

Rick DiPietro’s Career in New York

Rick DiPietro’s career with the Islanders was far less pleasant than anticipated. After just one season at Boston University, DiPietro immediately joined the Islanders organization and began in the AHL. For his first three seasons with the Islanders, DiPietro showed he wasn’t quite ready yet and played just 30 games. This was not too big of a red flag, though, as goaltenders generally take a long time to develop.

DiPietro was named the Islanders’ starter in 2004. He had a respectable season and showed glimpses of brilliance, which excited Islanders fans. DiPietro declined in 2006, but then-general manager Mike Milbury signed him to an outrageous 15-year contract extension worth over $67 million. He bounced back with an incredible 2007 season, and almost matched it in 2008. Perhaps DiPietro just needed time to be among the leagues’ elite goaltenders. 

Inexplicably, DiPietro took a nosedive after this 2008 season. He suffered injury after injury and never was the same again. DiPietro played just 50 games across the next five seasons until 2013 when the Islanders bought out DiPietro’s massive contract, which had eight years remaining. The Islanders agreed to pay DiPietro $1.5 Million annually, spanning all the way until 2029, when DiPietro will turn 48 years old. At least it doesn’t count against the team’s salary cap.

A majority of the reason DiPietro didn’t have a successful career was neither his nor the Islanders’ fault. Still, if the Islanders could go back in time, they’d definitely rethink DiPietro’s contract, and possibly even drafting him in the first place. What if they didn’t?

Dany Heatley

Let’s say hypothetically the Islanders drafted the next best guy, Dany Heatley, who the Atlanta Thrashers took second overall in that draft. It’s not like the Islanders wouldn’t have had goaltending. The Islanders traded Roberto Luongo to the Panthers immediately after drafting DiPietro. Luongo was drafted fourth overall three years prior to DiPietro, so he was the original plan to be the starter for the Islanders’ future.

If the Islanders didn’t draft DiPietro we can rightfully assume Luongo wouldn’t have been traded. The entire trade was Roberto Luongo and Olli Jokinen to Florida in exchange for Mark Parrish and Oleg Kvasha.

Parrish and Kvasha both played five seasons for the Islanders before both were traded in 2006. Both were good players but never superstars. Kvasha reached 50 points just once, and Parrish reached 60 points just once. Olli Jokinen, on the other hand, was also a top draft pick, drafted third overall in 1997 by the Kings, one pick before Luongo. Jokinen had a slow start with the Kings, prompting his trade to the Islanders. But Jokinen played poorly in his first and only season as an Islander.

So, instead of Rick DiPietro, Mark Parrish, and Oleg Kvasha, the Islanders could have easily had Roberto Luongo, Olli Jokinen and Dany Heatley. How does this affect the Islanders’ future? Let’s skip forward until 2007.

The Dream 2007 Islanders

First, we will assume that the Islanders never traded these three players nor lost them in free agency. In real life, Dany Heatley requested a trade and the Thrashers sent him to the Senators in 2005. Although, there’s speculation that Heatley’s main motive for the trade request was to move on from his tragic car accident where he accidentally killed teammate Dan Snyder. In 2006, Florida traded Luongo to the Canucks, but this was only because Luongo and the Panthers couldn’t reach a new deal. Luongo admitted that he was shocked by the trade.

All these players peaked in 2007, and the Islanders could’ve had them all. Dany Heatley had his famous “50 and 07” season as he scored 50 goals and 55 assists that year. Olli Jokinen had the 14th most points in the NHL with 91. Jason Blake had 69 points and deadline acquisition Ryan Smyth had 68 points. The Islanders signed Miroslav Satan in 2005 and Mike Sillinger in 2006, and both had 59 points. Lastly, Roberto Luongo had an incredible season in the crease, posting a 9.21 save percentage and 2.28 goals against average through 76 games.

The real 2007 Islanders squeaked into the playoffs as the eighth seed. I think this team would’ve earned eight more wins. This would make the Islanders the fourth seed, demoting each team it passed by one spot. 

In the playoffs, the Islanders would’ve taken on a 19-year-old Sidney Crosby and the Pittsburgh Penguins. The Penguins fell to the Senators in five games in real life. These Senators went on to advance to the Stanley Cup Finals, which is a tall order for these Islanders, but I still believe these Islanders could have defeated Pittsburgh in six games. This victory would have ended a 14-year playoff series win drought, a drought that in reality lasted 23 years.

The Islanders then would’ve played the second-seed New Jersey Devils. Like the Penguins, the Devils fell to the Senators in five games in real life. Still, even this powerful Islanders team won’t have an easy time beating these Devils. This could go either way, but I’ll go with our 2007 Islanders to edge off the Devils in seven games.

The Islanders would’ve done the unthinkable. They had found little to no success each year for the past decade-and-a-half. Now the Islanders have a date with the Buffalo Sabres in the Eastern Conference Finals. Once again, these Sabres lost to Ottawa in five games. In the previous Eastern Conference Finals, The Sabres lost to the Hurricanes in a seven-game heartbreaking series. They also had the best record in the Eastern Conference this year. The Sabres likely would have been too much for these Islanders to handle, and the Sabres would take the series in six games. 

The Sabres would go on to face the Anaheim Ducks in the Stanley Cup Finals. Like the Senators, they would lose. Unfortunately, even in this dream scenario, the Islanders still would have most likely not won the Stanley Cup in 2007. But the time period in Islanders history from 1995 all the way up until a few years ago is a pretty dark span, so a Conference Finals appearance in the middle of that span, even if it were just one year of fame, could have done a lot for the morale of the team and fanbase.

Ben Kule

Die-Hard Islanders fan and writer from Plainview, Long Island, NY. I have a passion and knowledge for this team and I enjoy sharing that with others