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Chester the Jester was a resident of Milbank 29 for a short time before his death in 2007, the details of which remain unclear.

He was a colorful inflatable jester that William Slater Welles purchased at Party City in the fall of 2006. Chester had a fan inside his feet that kept him upright for approximately half a year before the fan malfunctioned and he suffered a deflation from which he did not recover.

Renowned for his beauty (Welles called the drone of his electronic motor "mesmerizing"), reports of Chester's generosity have become legends. When the Hamilton College campus police controversially declared his presence in the Boneshack common room a fire hazard, Chester graciously relocated to a corner of the residence in which Andrew Peart was squatting.

It was in this room that Chester met his demise during what has been called both a "gentle embrace" and a "murderous strangulation" committed by Welles himself. Nick Fesette was present at the scene and is considered a first-hand witness but has so far declined to comment on the incident. Following the jester's death, Welles and Fesette buried him beyond Minor Field in a dirt pile.

It has become a tradition to visit the site of his burial and to "pour one out" for Chester the Jester.