Bill Oakley is a deputy district attorney.
Jimmy continuously attempts to plead with Bill to let off his client. Bill responds with the phrase "petty with a prior" each time he asks. They eventually come to an agreement when Jimmy makes a deal to get a continued sentence for his client and in return, if the client stays clean, Bill can file him for dismissal in six months. ("Mijo")
Jimmy comes to Bill once again for a deal for his client. Bill declines all of Jimmy's offers, telling him that his client drove drunk into a shopping center and killed three civilians. Jimmy corrects him and tells him that he is thinking of the wrong client. His client was only charged with armed robbery at a liquor store. The two then make a deal to let the client off in ninety days with good behavior. ("Nacho")
Bill meets Jimmy in the men's restroom and tells him that he has heard about Jimmy working at Davis & Main. Brimming with jealousy, he grills Jimmy about all the perks of working at the firm. ("Rebecca")