Ray's Goon is an unnamed henchman of Ray Boccino's. He appears only once in the mission Was It Worth It?, when he is seen torturing Jim Fitzgerald with a blowtorch in the basement of Drusilla's. While Johnny and Ray argue, Jim cuts himself free with a box cutter and takes the goon as a human shield. Before escaping with Johnny, Jim cut the goon's throat with the cutter, killing him and infuriating Ray. Shortly after the two escaped, Ray sent hitmen after them. While Johnny managed to kill the hitmen (optionally, with the help of Terry and Clay), Jim is murdered by the hitman sent after him.
- Was It Worth It? (Killed)