7 Biggest Trades in New York Islanders History, Ranked

Perhaps no team in the modern era has been involved in more blockbuster trades than the New York Islanders. 

From the trade that turned the Islanders into a dynasty to the wheelings and dealings of “Mad” Mike Milbury, Isles fans know better than most that a blockbuster deal can change the outlook of a franchise for a generation.

This was a hard one to whittle down, but here are my picks for the seven biggest trades in the history of the Islanders.

7 Biggest New York Islanders in Team History

1. Bill Harris and Dave Lewis for Butch Goring 

This trade happened in 1980, but it is still referred to as the benchmark for a deadline deal.

The Islanders were a powerhouse in the late 1970s and were regularly considered one of the favourites to win the Stanley Cup according to their NHL odds, but they kept stumbling in the playoffs.

The Islanders already had enough elite skill with Mike Bossy, Bryan Trottier, and Denis Potvin, but what they lacked was a solid checking-line centre who could take on some of the defensive responsibilities. 

Enter Butch Goring.

Goring’s addition not only spurred the Isles to success in the 1980 Stanley Cup playoffs, but for the next three postseasons, too. 

The Islanders are the last franchise in North American sports to four-peat (1980, 1981, 1982, and 1983), and they hold the record for most consecutive playoff series wins (19).

2. Zdeno Chara, Bill Muckalt, and a First-Round Pick for Alexei Yashin

This is a polarising trade.

You could argue that it was lopsided in favour of the Ottawa Senators, who landed Zdeno Chara and took Jason Spezza with the first-round pick they received, but the truth is that this deal was one the Isles needed to make.

The Islanders were not on stable ground at the turn of the millennium and needed some immediate success to avoid disaster. So they went out and acquired Alexei Yashin, one of the game’s most talented forwards.

Yashin would sign a massive contract with the Isles that would age poorly, but he led them to a vital playoff berth in 2001-2002. 

It’s not hyperbole to suggest that the Islanders may not have remained on Long Island much longer if they didn’t make the playoffs that season. 

3. Roberto Luongo and Olli Jokinen for Mark Parrish and Oleg Kvasha

This was one of “Mad” Mike’s worst moments. 

The Islanders looked like they had a franchise goaltender in Roberto Luongo, but Milbury felt so strongly about drafting Rick DiPietro, another goaltender, first overall in 2000 that he felt comfortable sending Luongo to Florida for a paltry return.

Luongo became one of the best goaltenders of his generation, while DiPietro flashed for a couple of seasons before injuries derailed his career.

4. Pat Lafontaine, Randy Wood, Randy Hiller, and a Fourth-Round Pick for Pierre Turgeon, Benoit Hogue, Uwe Krupp, and Dave McLlwain

The decision to deal Pat Lafontaine was a tough one, but the Islanders came out well ahead in this deal thanks to Pierre Turgeon.

The future Hall of Famer instantly became a fan favourite on Long Island and helped lead the Isles out of a post-dynasty malaise in the early 1990s.

Turgeon put up 340 points in 255 games and his 1.33 points per game is the second-best mark in franchise history behind Bossy.

5. Tim Connolly and Taylor Pyatt for Michael Peca

It is hard to overstate how crucial the 2001-2002 season was for the Islanders despite it ending in Round 1 of the playoffs.

The Isles were in financial distress for much of the 1990s and new ownership needed the team to improve from a team that was always a long shot according to their hockey odds to a contender.

With that in mind, the Isles got aggressive by trading for Yashin and Michael Peca in the same offseason.

While Peca didn’t bring the offensive firepower that Yashin did, his leadership qualities and ability to play any role were a massive reason why the Islanders made the postseason three years in a row between 2001-2002 and 2003-2004. 

6. Wendel Clark, Mathieu Schneider, D.J. Smith for Kenny Jonsson, Darby Hendrickson, Sean Haggerty, and a First-Round Pick

The Islanders were seemingly making trades every week in the late 1990s to balance the books and while many bit them in the behind, this blockbuster worked out brilliantly.

Wendel Clark was a fan favourite in Toronto, so the Islanders were able to get the Maple Leafs to pay a premium price for him despite his best days being behind him.

That meant the Isles were able to land Kenny Jonsson, a stoic defenceman who was a rock on the Isles’ blue line for their resurgence in the early 2000s.

Jonsson was elected into the Islanders’ Hall of Fame in 2012.   

7. Griffin Reinhart for a First-Round Pick and a Second-Round Pick

There are plenty of other trades that can fit into this list, but I’ll finish with the deal that landed Mat Barzal on Long Island.

Now the face of the franchise, the Islanders were able to nab Barzal with the 15th overall pick in the 2015 draft despite not owning a first-round pick when Draft Day began.

They accomplished this by sending Griffin Reinhart, a former fifth-overall selection, to Edmonton for a pair of picks.

The first was used on Barzal, who has a chance to become the best Islander since the Dynasty.