To achieve this goal the easiest way, you can drive the most expensive car in the game; the Duesenberg Walker Coupe, located in Hollywood at Santa Monica Blvd., between Vine and El Centro, in a Garage of a Palace-like building. Once obtained, wreck this car on other cars and the public. Stay around the spawning location for the Duesenberg and repeat this around 10 times.
When using the Duesenberg, or another expensive bonus car, such as the Phantom Corsair or Tucker Torpedo, build up some speed and smash head first into an oncoming car. If going fast enough, this will total both cars, yielding the maximum damage value. Repeating this action should bring the damage value to the threshold more quickly than smashing into light posts, mailboxes, etc.
Also consider using the American LaFrance Fire Truck located in the parking lot behind the Hollywood Police Station. This is the most expensive vehicle in the game.
One can also drive down crowded sidewalks, injuring passerby amounts to $100 for each citizen driven over.
The best time to get this trophy is to do it during your main playthrough of one of the short early story missions (Traffic desk or later), such as The Driver's Seat, because you'll obviously need to replay the case later to get five stars, and a short one is easier to replay. Accumulating penalties has no real impact to your game, other than the score of the case you're actually on. Another trick is to do it in one of the DLC cases if you have them, since there is no requirement to get 5 stars on the DLC cases.
- The amount of damage needed to be caused is an allusion to the year the game is set, in '47.
- If you have a Rockstar Social Club account you can track the damage done to your Vehicle, player damage, and the damage done to the city. All you have to do is visit the Social Club and click on the case you're attempting this Achievement/Trophy on.
- This Achievement/Trophy will not unlock until you reach the end of the case and view your report, and there's nowhere in the game to track it. If you're unsure whether or not you've caused enough damage, get to a save point in the game, quit to the main menu and sync with the Social Club. Then, head over to the Case Tracker to see the running total for the case you're on.