- "What'll it be, stranger?"
- —Chester to Marty McFly
Chester met Emmett Brown in January 1885, eight months earlier that year, when Doc Brown, by accident, landed there due to a freak mishap of a bolt of lightning striking the DeLorean time machine in 1955.
On July 4, he had to administer wake-up juice to Doc after he passed out having whiskey. On September 7, he monitored Doc as he held on to a shot of whiskey after losing Clara Clayton. Just as Marty McFly entered to convince Doc to leave, Doc drank the whiskey and collapsed into a table. Chester reacted quickly and attempted to sober him up. He recommended that his assistant Joey get some wake-up juice for Doc again. Upon reaching his throat, Doc reacted violently to the juice and ran into the horse trough, where he collapsed again in the cold water.