Raptors-Around time VC left
Leafs-"The Collapse"(2013 playoffs game 7) or when they finished 2nd worst in league and Bruins got that pick(Any pick not in the top 2 in that draft, and Leafs would've easily won Kessel deal)
Jays-Either right now(seeing team supposed to make playoffs,as bottom 5 in the league) or 2004 season where Jays finished with one of worst win% in franchise history(ironically,both seasons featured Gibbons).



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