- Salvatore Leone: "We cleaned it up with the Forellis. The Sindaccos we sent into the fucking sea. Now, I got the Sicilians on the phone, wanting peace. We all want peace! But my peace, not their fucking peace. I'm the big man now. No chump from the old country is gonna tell me what to do. I told them to go fuck themselves."
- Toni Cipriani: "You did? Was that wise?"
- Salvatore Leone: "Hey, I'm the boss now. ME! Now let's go see the mayor about getting my charges dropped..."
- —Salvatore Leone and Toni Cipriani about the pay a visit to Mayor Miles O'Donovan.
The Sicilian Gambit is the final storyline mission in Grand Theft Auto: Liberty City Stories, given to protagonist Toni Cipriani by Leone Family Don Salvatore Leone from his home in Saint Mark's, Portland Island, Liberty City.
Toni goes to Salvatore's home and finds him talking to the Sicilian Mafia, who want to make peace. Salvatore also wants peace but only on his own terms. He decides to pay Mayor Miles O'Donovan a visit, to talk about dropping the charges on him and quickly realizes the Sicilians are after the Mayor. Toni and Salvatore arrive at City Hall in Torrington, but are too late. Toni kills some Sicilian goons while Salvatore checks the Mayor's office, only to realize the Sicilians have already taken him.
- Salvatore Leone: "Torini... it figures. Give him up! The mayor is mine! THIS CITY is mine!"
- Massimo Torini: "Salvatore... Sicily never wanted questo schifo di citta. But, when tribute dried up, what could we do...? It was nothing personal."
- Salvatore Leone: "Nothing personal? After what you put me through! I'm gonna tear your fuckin' heart out!"
- —Salvatore Leone and Toni Cipriani confront Massimo Torini while he holds Miles O'Donovan hostage at gunpoint.
They head to a jetty in Newport and see Massimo Torini speed off in a boat, with O'Donovan hostage. Toni and Salvatore take a boat and give chase. Toni gets a minigun and destroys the boats and helicopter chasing them. They eventually reach Portland Rock, with the Sicilians taking the Mayor to the lighthouse. Toni and Salvatore shoot their way up Portland Rock and meet Massimo Torini, who holds O'Donovan at gunpoint. Torini explains what the Sicilians did to the city was nothing personal towards Salvatore, but he's having none of it. Torini escapes to a helicopter with Toni eventually destroying it, thus killing Torini in the process.
Toni and Salvatore return to Salvatore's home with the Mayor, who then realizes that he is going to be controlled by the Leones. They then head up to Momma's Restaurante, meeting Salvatore's uncle, and peace is confirmed between the Sicilians and the Leone Family.
Salvatore thanks Toni for his work, but is going to reward him with only a half of the million dollars he promised, because he can't put a price on the friendship they have.
The reward for completing this mission is $500,000 and the King Jumpsuit outfit is unlocked.
- Massimo Torini - Killed by Toni Cipriani for taking the Mayor of Liberty City Miles O'Donovan hostage, as well as attempting to take complete control of Liberty City.
- Various members of the Sicilian Mafia - Killed by Toni Cipriani for attempting to kill him and Salvatore Leone as well as getting in his way of killing Massimo Torini.
- The name of this mission may be a reference to the board game of chess and a very popular opening called the Sicilian Defense.
- When Salvatore and Toni travel to Portland Rock by boat no matter what weather it is (sunny or night) the weather will always turn to stormy.
- When Salvatore and Toni travel to Portland Rock by boat, the radio in the boat will be tuned to MSX 98 and "Renegade Snares" by the Omni Trio will always play. This song also appears on Midnight Club 3: DUB Edition and its remix, another popular Rockstar game.
- If the player fails this mission, the first part of the mission is skipped and the player will restart from the boat chase.
- After the boat chase, when going through the gate, the goon standing behind a pair of crates cannot be killed head on, because for some reason there is an invisible obstacle above the crates. The player has to circumvent it and go next to the goon in order to kill him.
- Miles O'Donovan and Uncle Leone appear for the first time in this mission, making them the only named characters to be introduced in the final mission of a GTA game.
- This is the only mission in the entire game that showcases Involuntary Ejection. For example, if a member of the Sicilian mafia collide into a solid object, they will be thrown through the front windshield of their Stinger.