It’s really the easiest example to come up with. If you asked most Philadelphia Flyers fans what is their worst trade in recent memory, they’d say James Van Riemsdyk for Luke Schenn.
The trade seemed reasonable at the time. “JVR” was playing terribly inconsistent for the Flyers, and he didn’t seem to have the wherewithal to take the next step as a consistent, top-line goal scorer. The swap was two high draft picks that each appeared to need a change of scenery to tap their high potential.
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Not much has gone right for the Maple Leafs the last few seasons, but that trade may be one exception.