- "What'll it be, stranger?"
- —Chester to Marty McFly
Chester met Dr. 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. When Marty asked why Doc was still unconscious after pulling him out of the trough, Chester explained that was merely a reflex action, and that it would take another ten minutes before Doc regained full consciousness.