|Actor||Adrian Glynn McMorran|
|Dates||???? - 2015 (spirit laid to rest by Sheriff Donna Hanscum, Officer Doug Stover and Sam Winchester)|
|Location||Cottage Grove, Minnesota|
|Occupation|| Children's Entertainer|
Chester was performer for kids' parties. Stan Hinkle and Phil Evans accused him of abusing their children. It was believed that he killed himself by jumping off a bridge after the accusations.
Chester returns as a vengeful spirit, possessing the old costumes he used to wear, in order to get revenge on the people that killed him. He first possesses a college student named Mike Hooks, who donned a rabbit head that was donated to a costume shop. Chester first pays a visit to Stan Hinkle's home, after Stan's wife goes to take out the trash, Chester has the possessed Mike beat Stan to death with a beer bottle and leaves the house before being picked up by the police. The police soon realize that the bunny head cannot be removed and place him in a holding cell. When Sheriff Donna Hanscum calls Sam and Dean to help investigate, they test him and ascertain he is not possessed by a demon. Later as Donna and Officer Doug Stover are attempting to transport him to the hospital, Chester wrestles free and attempts to attack Donna when Doug shots him, killing him and causing the bunny head to fall off. Next Chester possesses a harlequin costume worn by the high school mascot, Michelle, Chester enters Phil Evans office in the weight room, wielding a kettlebell and proceeds to bash his head. However Evans survives and is taken to the hospital, where he is left in a coma. At the station, Sam and Dean realize they are dealing with a possession and Dean shoots Michelle with a buckshot of rock salt, ejecting Chester from her body.
However the next day, Chester possesses a clown costume being worn by an elderly man named Steve Buress, as a clown Chester goes to the hospital where he finds a comatose Phil Evans and with a scalpel slashes his throat before calming walking away. He enters an elevator which Sam happens to be in. Able to get past his paralyzing fear of clowns, Sam is able to notice the bloody scalpel in the clown's hand, realizing the man is possessed the two briefly fight and Sam ejects Chester with an iron rail road spike. As Donna and Doug go around and collect all of Chester's old costumes to burn, Sam and Dean pay a visit to Chester's sister Rita who tells them that Chester did not commit suicide, Rita, fearful that the accusations against her brother were true had allowed Stan and Phil to go and try to scare him, the men had taken Chester to a bridge, where they threatened him, and in doing so he fell to his death. After hearing the story, Sam gets a call from Donna telling him they burned all the costumes, however Sam inquires if they burned a deer head among the costumes. Donna tells him they hadn't, when Max suddenly appears in the deer head and knocks Dean out. Max then knocks Sam back before Sam can press the iron spike to eject Chester, Dean wakes at the loud crash of Sam hitting the china cabinet and sees the possessed Max begin choking Rita. Dean grabs the iron spike and presses it to Max’s exposed back before he chokes Rita to death. Causing the Deer mask to fall to the floor. Sam jumps up from the broken glass and Dean tosses him the mask to go burn outside. Sam rushes out to the Impala while Dean gets Rita and Max into a salt circle in the living room. Outside Sam gets gasoline from the trunk, when Chester comes from behind and knocks him out. Back inside, Dean tells Rita and her son to stay inside the circle, explaining that Chester is a ghost, before Chester comes up behind him and throws him into the other room. Chester begins stalking towards Dean. Max calls out to him, causing Chester to pause, but then he pushes Dean against the wall and begins choking him. Outside, Sam has regained consciousness and douses the deer head in gas, and torches it. Inside, Chester suddenly stops choking Dean and begins to become consumed by flames before finally disappearing.