This trophy can be earned over the course of an entire playthrough but can of course be completely missable if you mess up a single button sequence. It’s highly dependant on your choices throughout the game because every playthrough is different, but there are several fight sequences that will occur.
They come in the form of fist fights, escape sequences, or gunfights. It’s recommended, to perhaps make this easier, that you set the difficulty to casual – you’ll only have to press X and circle during the fights and pressing one wrong button will not negate the trophy achievement. Only if you completely lose a single fight will you have to start over.
You’ll know if you’ve failed – too many mistakes will result in your characters getting badly injured or outright killed.