The Five Worst Trades in New York Islanders History

While the successes and steals of the past of the New York Islanders. are what we like to remind ourselves of, the closed-minded offseason moves of Mike Milbury and Garth Snow are the true testaments of an often underwhelming and disappointing era. It’s no secret that following the incredible successes of the 80s, the Islanders turned into a franchise of touch and go successes and ultimately to one of mediocrity.

The dark years of the late 90s and the teasing success of the 2000s came out of terrible trades and unfortunate draft picks, with improvements in management and much better scouting and coaching staff and system, it’s still important to look back on our mistakes before we’re doomed to repeat it as they say. Perhaps some of these trades are worse than others. We can all agree, however, anyone would hang up the phone on these trades looking back (and at the time).

5. New York Islanders Acquiring Alexei Yashin, the Ottawa Senators acquired Zdeno Chara, Bill Muckalt, and a 2001 first-round pick.

Off the bat, you might expect this trade to be the worst in Islander’s history. I give this one sympathy, however. It was not known that Zdeno Chara could become the shutdown d-man that will soon have been a defensive threat over four decades. Alexei Yashin was a very solid centerman, a consistent 30-40 goal scorer who had a natural offensive mind. At the time this trade made some sense, but looking back, the first-round pick became all-star Jason Spezza and the young lanky Slovak d-man turned into a cup raising captain. An unfortunate trade looking back.

4. Giving up John Tonelli to the Calgary Flames for Steve Konroyd and Richard Kromm.

Every franchise has a turning point. This trade was without a doubt a massive turning point and wake up call for fans. Things would differ from here on out. Through bitter contract disputes and an Islanders legend missing games because of stingy management, four-time cup champ, and 100 point player John Tonelli departed for a no named-man out of Steve Konroyd and non-NHL winger Richard Kromm.

The Islanders of the 80s were turning into a modern management joke. Aside from disrespect, the inability to correctly value an Islanders legend after taking a cup winning pay cut is the epitome of terrible management. Another franchise-changing move from Milbury, and it’s not even the worst of it.

3. Trading Roberto Luongo and Olli Jokinen to the Florida Panthers for Oleg Kvasha and Mark Parrish.

Originally, the face value for this trade made some sense. Playmaker Oleg Kvasha and Mark Parrish, who had a career-high of 30 goals with the Isles, added some short-lived depth to an Islanders team who desperately needed some postseason berths. The price was Olli Jokinen and a fourth overall draft pick, goalie Roberto Luongo. Olli Jokinen hadn’t produced like the intelligent centerman the Islanders needed. The year after he joined the Isles through a trade that gave Palffy to the Kings, Olli had barely reached 20 points. It was only after the Islanders gave him up that Olli turned into the 30 goal scorer. The role forward the Islanders had previously dreamed him up to be. Neither fates would have been worth it, however.

Then there’s the elephant in the room, Roberto Luongo. We all know the story. The goaltender played over two decades worth of jaw-dropping hockey. Recently having his number retired by the Florida Panthers organization. He played for so long and with so much success that he went from being traded by the Isles at the turn of the century to facing off against some Islanders of today in the 2016 playoffs and as recently as 2019. A HOF caliber goalie and an underestimated 30 goal centerman. All for two decent depth pieces. This lives as one of the most regrettable trades in the history of the New York Islanders. It surely would’ve changed a lot of our very recent history.

2. Trading Pierre Turgeon and Vladimir Malakhov for Kirk Muller, Mathieu Schneider, and Craig Darby of the Montreal Canadiens.

A trade to make your head hurt. Pierre Turgeon, an Islander legend, was a key part of the 1992-93 postseason success. He recorded 58 goals for 132 points. Enough said. He would have been a franchise cornerstone for the relatively new decade. Unfortunately for him and 50 point defenseman Vladimir Malakhov, it was the decade of Mike Milbury. Their career-best years with the Islanders would end with a trade to Montreal for three nobodies. Neither Muller, Schneider, or Darby would have success with the Isles, as the team fell flat on their face in the standings. If this trade hadn’t had gone down, Turgeon and Palffy would’ve skated together. Those two along with Chara and Jason Spezza would’ve undoubtedly been a cup contending team.

1. The New York Islanders trade Zigmund Palffy, Bryan Smolinski, Marcel Cousineau. As well as a 1999 Fourth Round Pick to the LA Kings for Olli Jokinen, Mathieu Biron, Josh Green, and a 1999 First-Round Pick.

A blockbuster trade, this Mike Milbury beauty was one of the worst trades to grace the financial records of the New York Islanders franchise. The islanders received three no names. The best of which: Olli Jokinen, only spent a year with the Islanders before he was traded along with Roberto Luongo. A Mike Milbury feat previously mentioned.

The Islanders also received a first-round pick that turned into a major bust, Tim Connolly. While a first-round pick and NHL ready prospects seemed like a good return, the return was Zigmund Palffy. If you grew up in the 90s you know the name, an all-star offensive powerhouse. Palffy was a 40 plus goal scorer on one of the worst teams in the league. A guy to rebuild around. At 24 he scored 48 goals for 90 points. He assisted on the gold medal-winning goal for his native Slovakia at the 2002 Worlds. Palffy wasn’t the only talent the Islanders were giving up for next to nothing. Bryan Smolinski was an intelligent puck-moving centerman who listed a career-high 28 goals with the Isles. Another talent gave away by Milbury. 

If Milbury had his wits about him, the Islanders could have had a team with Chara, Jason Spezza, Pierre Turgeon, Vladimir Malakhov, Bryan Smolinski, Roberto Luongo, and Zigmund Palffy all at the same time. That foundation and just a little bit of money management and good coaching is a cup caliber team. But the Islanders got on and off seasons and often mediocrity over for the late 90s and early 2000s.


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