In 1987, Jake, while painting one of the Pinehurst walls alongside fellow Pinehurst resident Violet, notices Sheriff Cal Tucker and Deputy Dodd drive up to Pinehurst to drop off halfway house residents Eddie and Tina, who were found having sex on the nearby property of Ethel Hubbard. Going to see what the commotion is, Jake, along with the entire Pinehurst establishment, is threatened by Ethel Hubbard and her son Junior, who appear to voice their outrage that Eddie and Tina were trespassing on their property again. When the police and Hubbards leave, Jake, along with everyone else present, disperses. A clearly disturbed Jake was later present when the police arrest Pinehurst resident Vic for murdering Joey, another halfway house resident. Jake also later attends dinner at Pinehurst, where he witnesses new arrival Tommy Jarvis attack Eddie after a prank gone awry. When residents and staff of Pinehurst begin disappearing, Jake, along with housemates Violet and Robin, inform the halfway house assistant director Pam Roberts, who had been visiting relatives of a boy named Reggie, of this. Before she goes off to search for the missing residents and staff, Pam leaves Jake in charge of the house, also leaving Reggie in his care. While watching the film A Place in the Sun with Robin in the halfway house living room, Jake struggles to reveal his true feelings to the obviously distracted Robin. After managing to awkwardly tell Robin that he really likes her before asking if she would sleep with him, an embarrassed Jake leaves the room after the bemused Robin begins hysterically giggling at him. Going upstairs, a heartbroken Jake seeks solace with Violet, who was in her room in the midst of dance practice. At first unable to hear Jake over her blaring music, Violet, after Jake asks if they can talk, tells him to come back later and asks him her last line "Can it wait?". Even more dismayed than before, Jake replies with the his last line "No." and closes Violet's door and begins heading to his room, only to be killed when Roy Burns strikes him in the face with a meat cleaver. 
Later, Robin, while getting ready for bed, finds Jake's bloodied body under her sheets. Jake's body, moved onto Tommy's bed, is also found by Reggie and Pam, who discover it in a pile with the corpses of Robin and Violet.
- Jake's death scene was one of many to be censored by the MPAA. Recently uncovered stills reveal deleted footage of the meat cleaver actually hitting him in the face.