Joseph Daniel O'Toole

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The manager of Paulie's Revue Bar (named after Paulie Sindacco) Joseph Daniel "JD" O'Toole is an Irish and overweight pervert who runs the business. He is spat on by the other Sindaccos for not being full-blooded Italian and is upset that they have not "made" him yet. The disgruntled JD becomes a mole for the Leones and starts leaking them information.

He helps out by thwarting an attempted assassination of Salvatore, tipping Toni off to an assault on a Leone gaming house, and helping to blow up the Sindacco's brothel/casino (the "Doll's House"). These victories eventually lead to a gang war in the Red Light District, where the Leones manage to drive the Sindaccos out of the area (and out of Portland in general). Paulie's Revue Bar comes "under new management" and is later converted into Sex Club 7.

JD was once arrested for statutory rape, even though the girl he slept with was said to be 18, and was apparently raped in prison. He was also suspected of downloading child pornography, but was never arrested for it. At first, Toni finds him revolting, but they develop a bit of camaraderie as JD's info leads to Toni's rapid ascension within the Leones.

JD is killed on the day of his "made" ceremony. He is lured to a secluded area beside the car crusher and shot at the back of the head by a Leone enforcer, Mickey Hamfists - under Salvatore's orders; the ever-paranoid Salvatore could never trust a former snitch. JD and the car where he is killed in are then dumped into the sea (of the player's choice).

JD O'Toole was voiced by Greg Wilson.