Cy has an year relationship with former prostitute and madam Joanie Stubbs , who later leaves the Bella Union to form her own brothel, leaving a mix of friendship and anger between them. Cy is clearly in love with Joanie and is bitter not to have his feelings reciprocated. He also becomes partners with Mr. Lee dead and Cy receiving a knife to the stomach courtesy of Andy Cramed.
He survives but becomes increasingly desperate and unstable. Though he clearly despises Tolliver, Hearst employs him to act as his agent, but Tolliver finds Hearst difficult to work with. When he hands him an advantage, having discovered that Leon is dealing dope to Alma, Hearst rants angrily that he should have told him sooner. When Hearst leaves camp, he puts Tolliver in charge of his "other-than-mining interests," as Cy snidely puts it, making him angry at Hearst for all but eliminating their business together.
Soon afterwards, Tolliver exits to the Bella Union balcony accompanied by Leon and a prostitute. He stabs Leon and tells him he's stupid for congratulating him on his remaining business with Hearst. In his anger he points a gun at Hearst's coach as it readies to leave the camp, but does not shoot him. Instead he presses the gun to the prostitute's forehead, before regaining his calm and returning inside.
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