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Double or Nothin'

Put all your money or the maximum bet on red or black and win.

This is another trophy/achievement that involves gambling, although you won’t be able to get it until you reach Las Venturas. Once you do, you will be able to visit a casino, and subsequently, the roulette tables. With access to those, go to one of them and bet the maximum bet on either red or black. Keep doing this until you win from either of the bets, which will unlock this.