|For the deleted mission with a similar name from Grand Theft Auto: Vice City, see Chaperone....
- "Me an' the fellas have to talk business, so you're gonna look after my girl for the evening."
- ― Salvatore Leone
Chaperone is a mission in Grand Theft Auto III given to protagonist Claude by the Leone Family Don, Salvatore Leone from his mansion in the Saint Mark's district of Portland Island, Liberty City.
Salvatore and 'the fellas' are going to discuss business and he wants Claude to look after his wife, Maria Latore. Using the same black Stretch driven in "Salvatore's Called a Meeting", Maria asks Claude to drive her to her drug dealer, Chico, who is at the Kurowski Station for the Portland El service in Chinatown. Claude complies and whilst she is talking to Chico, he tells her of a party taking place in a warehouse in Atlantic Quays. Maria has Claude drive her to the party, which is raided by the Liberty City Police Department. Maria manages to get back into the car driven by Claude, who drives her back to Salvatore's Gentlemen's Club.
The reward for completing the mission is $10,000 and the missions Cutting the Grass for Salvatore Leone and Triads and Tribulations for Toni Cipriani are unlocked. Any incomplete missions for Luigi Goterelli and Joey Leone also become available again.
- Chico - Can be killed after Maria speaks with him.
Claude parking up to Chico in Chinatown.
Claude dropping Maria off at the warehouse.
Teams raiding the party.
Claude bringing Maria back to the club.
- The music heard from the party is a sampled version of "Animal Testing Centre - DSP". The original version appeared on The Fix FM in Grand Theft Auto 1.
- The subtitles are incorrect when Maria is talking to Chico. He says "mira", which means "look" in Spanish, but the subtitles show "Maria" instead.
- The LCPD Dispatcher makes a specific announcement during this mission while Maria is in the club: "Four-five to all units: Assist narcotics raid Atlantic Quays."
- The Enforcer arrives at the scene while the wanted level gained is three despite this vehicle normally only being seen during a 4-star wanted level.
- This is the first storyline campaign where a Cheetah appears (excluding Vigilante/Firefighter side missions) and is also the first time it appears in Portland.
- If those parked vehicles aren't destroyed, some participants will flee in them, otherwise they flee on foot instead.