Ranking the Top 5 Biggest Toronto Maple Leafs Trades of the Decade

3. James van Riemsdyk for Luke Schenn

In a draft-day deal that the Philadelphia Flyers certainly regret, they were fleeced into giving up a former second-overall draft choice in exchange for a defenseman who never reached his potential.

On June 23, 2012, the Maple Leafs picked up James van Riemsdyk in exchange for Luke Schenn.

It was a swap that the Toronto Maple Leafs general manager Brian Burke and Flyers GM Paul Holmgren had been working on for months. The deal finally got done on the second day of the 2012 NHL draft.

The Flyers gambled that Schenn would be a pivotal part of their blueline and reuniting him with his brother Brayden would elevate both players.

They were willing to part ways with a 23-year-old van Riemsdyk to do make that happen. They felt that van Riemsdyk was expendable because of the injuries that had plagued him the previous season, limiting him to only 43 games.

JVR became one of the Toronto Maple Leafs best players throughout his entire stay with the team while Schenn eventually found himself in the bottom pairing in Philadelphia. As a stay-at-home defenseman who wasn’t able to elevate his game in the NHL, the Flyers never got the value they hoped from Schenn.

JVR spent six years with the Leafs before the salary cap kept them from extending him. In that time he played 413 games and picked up 294 points.

That included his 2017-18 campaign when he scored an impressive 36 goals. He was known to set up shop near his opponents’ net and use his impressive hand-eye coordination and quick release to pick up goals in bunches.

Van Riemsdyk was one of Toronto’s best wingers of the decade and it’s all thanks to this mega deal.