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1986 – Spud Webb
Shoe: Pony City Wings Low
Spud Webb not only conquered his own height with his 1986 title. The shortest contest winner ever also beat Atlanta Hawks teammate Dominique Wilkins, whose dunking prowess is still revered today. Spud chose the low version of the Pony City Wings in a white, red and black colorway to help him capture the crown. (Commemorative retro release pictured above)