@ Em
Yes, the trophy is accumulative and there's also an optional side mission in the game that lets you play Poker and offers you about $2000 but I'm not sure if it counts towards the trophy or not? Just play on the highest difficulty and keep doing All In, you should have it in no time. If you're feeling a bit curious on where you're at in Poker in terms of money, just press Start, Handbook, then Square for statistics and go to world. That should show you how much you've earned over the entire course of your Poker time.
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