There are multiple examples of the Leafs trading away their first-round pick way too early and it blowing up in their face. It’s amazing that the organization didn’t learn its lesson after the 1991 debacle.
In 2009, the Leafs gave up two unprotected first-round picks for Phil Kessel, which ended up being Tyler Seguin and Dougie Hamilton. At least Kessel was a great player in Toronto, so you can argue the merit of the deal. There’s also the re-acquisition of Wendel Clark, which resulted in Toronto giving the Islanders the pick they used on Roberto Luongo.
But before both of those deals came the infamous Tom Kurvers acquisition, far and away the worst deal of them all.
In the late-80s, the Leafs appeared to be turning the corner from the laughingstock they had become at the beginning of the decade. A young core of players like Wendel Clark, Vincent Damphousse, and Ed Olczyk helped Toronto to three-consecutive playoff appearances (and two series victories) between 1986 and 1988.
The 1988-89 season was a step backwards as the team would miss the playoffs after posting a paltry 28-46-6 record. The following off-season, general manager Gord Stellick would resign …
Author: Cam Lewis / The Leafs Nation