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Get arrested 50 times.

In order to get arrested you need to "break the law" and obtain at least a one star wanted level. Your current wanted level is displayed in the top right corner of the screen. The easiest way to obtain a one star wanted level is to attempt to hijack a police car by pressing (triangle). The cops will immediately get out of the car and arrest you. Once you are arrested you will be transported to the closest police station.

To grind this trophy out, simply re-enter the police station and punch the closest cop by pressing (circle). They will continue to hit you until you fall to the ground, at which point they will pull out their gun and arrest you and the busted screen will display. You must see the busted screen in order for it to count as an arrest, if you are killed by the cops it will register as a death as opposed to an arrest. The below video shows this method, as well as the location of the police station in Downtown Los Santos:


Each time that you are arrested you will lose all your weapons and money, so it is best to grind all 50 arrests at a single time to avoid losing your weapons later in the game. Alternatively, you can just create a new save file and then complete them on an alternate save file. However, you will need to obtain all 50 arrests on the one save file.