Islanders Top 3 trades with the Toronto Maple Leafs

The New York Islanders logo (Photo by Bruce Bennett/Getty Images)
The New York Islanders logo (Photo by Bruce Bennett/Getty Images)

With a long offseason, let’s take a look at some of the best trades between the New York Islanders and the Toronto Maple Leafs.

This offseason is dragging on and because of it, it’s tough to come by any news. So while we wait for the New York Islanders to do something, I wanted to take a look at some of the best trades the Isles have made with the other teams in the league.

First up, the Toronto Maple Leafs. I wanted to look at some of the better trades between the two now rivals since 1972 when the Isles entered the league. I found three as well as an honorable mention.

Wendel Clark Trade

On March 13, 1996, the Islanders sent three players to the Maple Leafs (Wendel Clark, Mathieu Schneider, and D.J. Smith) for a return of three players plus a pick (Sean Haggerty, Darby Hendrickson, Kenny Jonsson, 1997 1st).

For the Leafs, they were trying to get back to make up for that first-round loss to the Blackhawks in 1995 by going big at the trade deadline. Getting former captain Wendel Clark was one of those big moves.

But when you make a big move you have to pay a big price. That first-round pick would be the fourth overall, the Isles used it to nab Roberto Luongo.

Johnsson wasn’t the key piece of the trade but ended being a key piece on the Islanders blueline over the next nine seasons.

Meanwhile, the Leafs crashed out of the playoffs in the first round once again in 96 this time to the St Louis Blues.

Trading Down at Draft

At the 2008 draft, the Islanders traded down from the fifth overall pick to the ninth overall pick in two separate trades. The first was with the Leafs where they sent the fifth overall pick for the seventh, 68th, and the 37th in 2009.

The Leafs would select defenseman Luke Schenn. Four years later they would trade Schenn for Jame Van Riemsdyk after Schenn failed to live up to the hype.

The trade allowed the Isles to get extra picks and move down to (eventually) select Josh Bailey ninth overall.

Now, yes, Bailey didn’t have a great start in the NHL. It took him years to be the guy he is now. And yes, after finding a spot on the Tampa Bay Lightning, Schenn won a Cup and Bailey has not. (I’m sure I’ll hear that a lot.) But Bailey has been a key piece for the Islanders for years now even earning a trip to the All-Star game.

Matt Martin

One of Lou Lamoriello’s first moves since getting the job on the Island was to trade AHL goalie Eamon McAdams to the Leafs for Matt Martin, a guy he signed as GM of the Leafs.

It gave the Leafs some cap space but it also gave the Islanders their fourth-line back. And as we all know that fourth line is vitally important for the Isles, who drive their identity from the combo of Martin-Cizikas-Clutterbuck.

Martin’s value was on clear display in the playoffs when he scored five goals as the Islanders marched to the Eastern Conference Finals. Martin’s five goals were more than Auston Matthews, John Tavares, and Mitch Marner combined in the 2020 playoffs.

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Honorable Mention: Darius Kasparaitis

In 1992 the Islanders moved up from the eighth overall pick to fifth overall. The Leafs acquired Brandon Convery and Jim Carey while the Islanders got Darius Kasparaitis.

His stay on the Island was relatively short (four-ish years) but boy was it meaningful. Now one has or ever will dish out a better hip-check.