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Some time prior to his introduction, Jesse became a Vassal within the New Jersey Chapter of The Order's 4th Enclave. After Greg began experiencing strange occurrences as a result of living across from one of The Order's meeting places and had an encounter with the Slender Man, Jesse convinced his friend to join the organization. Greg later expressed a desire to leave The Order, concerned by its cult-like practices. Jesse warned Greg that defection would result in death, insisting that Greg was one of the chosen ones, prior to the Slender Man appearing in Greg's house and killing him. Jesse then took Greg's copy of the Collective Knowledge and fled.
Jesse is first introduced during Log #14-1. Greg throws a party at his house, and Jesse starts to become concerned when Greg is nowhere to be found. Jesse and Alex help Chris break into Greg's house, worrying that something may have happened to him. When Chris also doesn't return, Alex follows him in. Alex lets Jesse into the house as well and they both descend into the basement together, where they discover that Greg has been murdered. While Alex finds that Chris has been left unconscious, Jesse vomits into a toilet. From that point on, Jesse begins helping Chris and Alex in their search for answers. He is the one who ends up finding the Black Book at the Rainwood Day Camp & Learning Center and later accompanies them on their journey to the Atlantic Test Site. When Chris and Alex stay over at Jesse's house one night, KindVonDerRitter breaks in and leaves behind his knife as a peace offering. Jesse later helps Chris and Alex steal the contents of the chest owned by Heather McComber.
When Chris, Alex, and Greg's brother, Jeff, look through the tapes Greg had filmed during the final weeks of his life, they discover that Jesse is actually a member of the New Jersey Chapter of The Order and that he had convinced Greg to join the organization as well. When Noah Maxwell decides to interview The Order, he gets the location from Jesse. Jesse later leads Chris and Alex, who were secretly attempting to capture and interrogate him, into a trap set by The Order's heretical sixth enclave. His superior then hands him an axe and offers him the title of "Archvassal" in exchange for beheading his friends. Jesse is unable to go through with murdering them, and Jeff arrives to save them soon after. Chris and Alex later successfully capture Jesse, but are forced to flee before they can finish interrogating him.
Jesse then disappears for several months. On March 15, 2013, the two-year anniversary of Greg's death, Jesse is executed by The Order for breaking several of the organization's laws and being seen in the company of the heretical 6th Enclave. At the execution, the Overseer states that Jesse had been in line to one day lead the New Jersey Chapter's newly-installed fifth enclave, had he not committed such offenses. His beheaded body is discovered in a shallow grave at Shadowbrook Farms by the property owner, Giovanni Kraska.