Joseph Daniel O'Toole was born in Liberty City, he is a member of the Sindacco Family and the manager of Paulie's Revue Bar, named after Sindacco Family Don Paulie Sindacco. He was arrested, at an unknown time, for statutory rape, even though the girl he slept with was said to be eighteen, and was raped in prison because of that. He was also suspected by the FBI to be downloading child pornography, but was never arrested for it. O'Toole, having an Irish ancestry, is upset with Paulie Sindacco as he has yet to be "made" due to not being an Italian. O'Toole then begins to work for the Leone Family and employs Toni Cipriani, after Cipriani kills some of the Sindacco mobsters at a construction site in Hepburn Heights, which O'Toole filmed to release later as a snuff film. Cipriani first helps O'Toole by driving his van around the Red Light District to allow O'Toole to get his cut from his prostitutes and then informs him that the Liberty City Police Department are going to raid his club, allowing Cipriani to rescue Don Salvatore Leone. O'Toole continues to feed Cipriani information, allowing Cipriani to protect a Leone casino in St. Marks and then to destroy the Sindacco run 'Dolls' House casino.
Cipriani begins to work for Salvatore Leone and his wife, Maria Latore, but again works for O'Toole, firstly rescuing Salvatore after he was kidnapped from Paulie's Revue Bar and later protecting Salvatore when he personally goes to kill the Sindacco mobsters at the club. O'Toole later has Cipriani follow Massimo Torini, a high-ranking member of the Sicilian Mafia, who Salvatore correctly suspects is planning something in the city. Salvatore later decides to 'make' O'Toole and has Cipriani and Mickey Hamfists accompany him to the Harwood Autocrusher and Junkyard, where O'Toole is killed by a shot to the back of the head, fired by Hamfists, who explains that O'Toole could not be trusted after turning against the Sindacco Family. Cipriani later disposes of his body, dumping the body and car into the sea.
Sometime after the events of GTA Liberty City Stories his former club is taken over again by Luigi Goterelli and is renamed Luigi's Sex Club 7. This decision also marks the beginning of the end to Sindacco interests on Portland and later Liberty City.
- GTA Liberty City Stories
- Snuff (Voice)
- Bone Voyeur! (Boss)
- Don in 60 Seconds (Boss)
- A Volatile Situation (Boss)
- Blow up 'Dolls' (Boss)
- Contra-Banned (post-mission phone call)
- Salvatore's Salvation (Boss)
- The Guns of Leone (Boss)
- Calm Before the Storm (Boss)
- The Made Man (Boss/Killed)
- The execution of Joseph Daniel O'Toole, being shot in the back of the head in a car in a secluded area whilst on an apparent assignment, is similar to the execution of Paulie Gatto in the novel and film The Godfather.
- JD's Favorite radio station is Flashback FM.
- For some reason, JD owns a fireproof Rumpo, that has an unique Vanilla-cream color.
- O'Toole also appears to take influence from Henry Hill in the film Goodfellas, both having Irish ancestry and not being made because of this.
- His last name may be a reference to Ottis Toole, a man who, in 1981, kidnapped and killed two children.
- A tombstone for O'Toole is placed at the Liberty City Cemetery, despite his body being disposed of in the sea.
- In the mission Salvatore's Salvation, O'Toole suggests that his uncle is a pedophile.
- In a beta screenshot of GTA Liberty City Stories, O'Toole is shown to wear purple glasses.
- Since he also works for the Sindacco Family who watch JD constantly and who are the Leone enemies, you can't do his missions if you wear a 'Leone's suit'.
- His computer harddrive was searched at least once by the FBI for downloaded porn.
- A figure wearing a cowboy hat can be seen in the back of O'Toole's concept artwork, in the door of his strip club, which is suggested to be Avery Carrington.
- The shadowy figure as stated above may actually be Ned Burner as it appears the figure is wearing a trench coat indicated by the shoulder straps. This can also explain O'Toole's knowledge of Sindacco plans and Burner's interest in Toni Cipriani.