Beat it in 2 minutes by robbing ATMs until I had over 1k in cash, then I went down to the gang hideout, played Russian Roulette with 50/50 odds three times, after which I went next door and payed off my debt.
Played a whole bunch of times, though. Robbed banks, did deliveries, gambled, what have you. This game gives heavy "Streets Of Rogue" vibes with an art style boasting your usual retro flair, which I love very much. Genuinely an amazing game. Gonna try to figure out how to get that second trophy, now.