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'Cyrus "'Cy" Tolliver (Powers Boothe) is the owner of the upscale Bella Union saloon and Al Swearengen’s main rival. Cy has an 18-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. Ruthless and with a veneer of class and polish, Cy soon proves that while he may lack his rival’s skill in cunning duplicity he makes it up in ambition, becoming temporarily allied with the Hearst combine in Season 2. He also becomes partners with Mr. Lee, the newly arrived Tong leader from San Francisco, in “Celestial’s Alley”, an area of low priced gambling and Chinese prostitution that sees women placed in unspeakably horrid conditions, a fact Cy dismisses as a mere “cultural difference.” However he does accept Doc Cochran's offer to treat them for free, as a condition of Cochran's continuing to treat Tolliver's white prostitutes. As Season 2 climaxes Swearengen ends out on top, leaving Cy Tolliver in a weakened position; with both Francis Wolcott and 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.