- Kidnapper: "I'm a king, and Bleeter is my kingdom."
- Jimmy: "Okay, umm, that's pretty sad."
- ―One of the Kidnappers talking to Jimmy during ransom.
Michael receives a call from Jimmy, but as soon as Michael answers, he realizes something is wrong. Jimmy is talking to a stranger who is mad at him for trolling on the internet. Jimmy asks if his mysterious captors are taking him up Banham Canyon in a Landstalker just to punish him.
The player can choose whether to assist Jimmy. If the player refuses this mission, Michael will have to pay $10,000 in ransom money. If the player accepts, Michael follows Jimmy's directions to the Landstalker in which Jimmy is being held, all the while listening into a conversation between Jimmy and one of the men holding him; that man is a comedy writer who Jimmy has been harassing on Bleeter. Once Michael locates the Landstalker, he damages it to the point that Jimmy's captors exit the Landstalker and flee. Michael gets in the Landstalker and drives Jimmy to the Richman Hotel.
- Save Jimmy.
- Trash the kidnapper's car.
- Go to the car.
- Take Jimmy home.
- A glitch on this mission can render the Landstalker invisible. This can be fixed by taking a taxi to the vehicle and skipping the journey.
- Jimmy De Santa - "I've learned my lesson. No more flaming people online unless it's 100% anonymously."
- Trolling is the act of deliberately harassing other people or making fun of them, which is also a major problem in multiplayer.
- Unique dialogue will be used if the player chooses to drive Jimmy back home with the Landstalker, in which Jimmy will be revolted by an unpleasant smell in the car.
- If the player chooses to kill Michael, this will be the last appearance of Jimmy.
- Despite Jimmy stating the Landstalker is a charcoal color, it may sometimes appear in either blue or green instead.