This is trophy is random and can take to 2 minutes or 2 hours (Never had it take 2 hours but you never know). To earn this trophy you need to hit a Jackpot at one of the slot machines in Fort Frolic. A jackpot is 3 $ signs in a row and when you win, it will basically fill your wallet to $500 which is full. Fort Frolic has quite a few areas with slot machines so my advice would be to go in with a fairly full wallet, find a machine (there are 2 on the left as soon you go through the door getting off of the bathysphere), make a manual save, then start playing. If you run out of money, just re-load your save and you will have your money back. Keep playing until you hit the jackpot and when you do, you will hear a special chime/sound something and the trophy will unlock shortly afterward.