Played by Powers Boothe
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.