Al Swearengen's worst nightmare came true when Cy Tolliver brought his own den of gambling and whoring to Deadwood from Chicago. Tolliver's Bella Union is a high class joint, offering more refined and well-kept prostitutes along with sophisticated gaming, including craps.
A former riverboat gambler, Tolliver has been around, and he sees the unlimited earning potential the lawless town of Deadwood offers. Having done his homework and placed his own spies in town, Tolliver quickly establishes that he's not afraid of going head-to-head with Al, and he is just as calculating and wily as his competition.
When he learns that Al has killed Jimmy Irons in retribution for the ambush of one of Mr. Wu's opium couriers, Cy uses the opportunity to incite racial discord in Deadwood, something he believes will help him expand his turf. He later offers to bribe an army general with $50,000 in gold to garrison in town-and provide de facto enforcement for his own agenda.
A man who could ruthlessly execute two children who intended to steal from him, Tolliver seems to have only one weakness: his affection for his madame, Joanie Stubbs. When Joanie chafes under his authority, he offers to give her anything she wants, even if it means leaving his operation to set up her own whorehouse.