As he puts a shotgun in his mouth, a hunter's dog runs off with his tin mask. Richard chases the dog, and finds two hunters sitting around a campfire, who convince him to keep on living. Richard serves as Jimmy's lieutenant throughout a turf war with Nucky, and remains loyal even as they suffer serious financial losses. Richard is devastated when Angela is murdered by Manny Horvitz (William Forsythe) as revenge for an attempt by Jimmy to kill him over a $5,000 debt Jimmy refused to pay him, and begins to wonder if their business is worth the price they pay. To mend fences with Nucky, Richard and Jimmy go to Alderman James Neary (Robert Clohessy), scheduled to testify against Nucky, force him to type a note at gunpoint exonerating Nucky, then Richard shoots him in the head and stages his death as a suicide. When Nucky calls Jimmy and says they have captured Horvitz, both Jimmy and Richard sense a trap, and Richard offers to go along. Jimmy refuses, however, and tells Richard to live a good life. After Jimmy is murdered, Richard moves in with Jimmy's mother Gillian (Gretchen Mol) at her estate. One year later, Richard is a permanent resident in Gillian's brothel. Richard now acts as a caretaker at the brothel, and looks after Jimmy's son Tommy. Richard also seeks vengeance on Manny Horvitz, who has now become a partner in Nucky's gang, for Angela's death. On New Year's Eve, Richard waits outside Manny's house, and after killing Manny's driver, shoots Manny in the face with a shotgun as he opens the door to leave. Richard ventures off one evening to a veteran's legion for support and to discuss compensation which has been promised to wounded veterans. It's here that Richard meets Paul Sagorsky (Mark Borkowski), a bitter drunk who lost his son in the war. Richard looks after Paul when he is injured in a bar fight, and meets Paul's daughter Julia (Wrenn Schmidt). He falls in love with her, and they begin a courtship, despite her father's objections. Later in the season, Gillian's brothel is occupied by New York gangster Gyp Rosetti (Bobby Cannavale), who is at war with Nucky. Fearing for Tommy's safety, Richard attempts to remove the boy to Julia's house, but Gillian finds out about the plan and, angered, she has Rosetti's men kick Richard out.