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Phillips is actually in the employ of Leander Cephas Whitlock, and works for the Pinkerton detective agency.
Phillips visits the home of Gillian Darmody, looking to buy property in Atlantic City. He decides that it is too big for him but asks her to help him become familiar with the city. ("New York Sour") He appears to fall for Gillian, who begins to change her ways. Roy helps Gillian get off heroin.
|Season four appearances|
|"New York Sour"||"Resignation"||"Acres of Diamonds"||"All In"|
|"Erlkonig"||"The North Star"||"William Wilson"||"The Old Ship of Zion"|
|"Marriage and Hunting"||"White Horse Pike"||"Havre De Grace"||"Farewell Daddy Blues"|