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Cy Cyrus "Cy" Tolliver " You can help your delicate sensibilities by turning the fuck away. 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. Ambition Is Evil : Cy has great plans for his future, and his ambition results in him making more and more monstrous and sometimes ill-advised decisions that even Al would balk at.
Ax-Crazy : His nifty dress sense and quick smile are a thin veneer for what he truly is: a vicious jackal who kills before thinking. Bad Boss : Cy bullies, threatens and outright murders his employees from time to time.
Big Bad Wannabe : He's essentially a darker version of E. Farnum - a Smug Snake who desperately wants to be a major player in the town's politics, but whose poorly executed schemes and toxic personality leave him at the mercy of bigger predators like George Hearst. Bitch in Sheep's Clothing : He can pretend to be civil Swearengen: Sometimes I wish we could just hit 'em over the head, rob 'em, and throw their bodies in the creek.