Billy is first and foremost a businessman who will take your case for profit and then find ways to exploit the jury, find loopholes in the system, and ensure you get off, scot-free. Once he takes on Roxie’s case, he starts educating her on how to walk, talk, and behave to most appeal to a jury. He tells her to play up how she is just a sweet, misguided domestic housewife. He forces her to wear dowdy clothes and look “sweet,” while flashing the jury a bit of leg. Roxie rather resentfully imagines him as her puppet master; she merely parrots whatever he tells her to say, as he talks through her. Billy needs to drum up sympathy for her and make it look like the cops framed her, so he actually works against her in court by planning false evidence and having Velma testify that she found a diary where Roxie confessed. He can be charming and easily win people over, but… he really doesn’t care unless they bring the cash.

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Billy is as unscrupulous and ambitious as they come. He wants to win and it doesn’t matter how he gets there. He will help Roxie fake a pregnancy and find witnesses to testify to it. He is forever chasing after the next big, high profile case, with the prettiest girl at the forefront of it, because he knows it will bring him fame and fortune. He is arrogant, self-promoting, and insists that he could get off even Jesus, given half the chance. His ‘helpfulness’ is mostly oriented toward profit, much like Mama. But he can appear to be genuine and generous, when it suits him.