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Are there special requirements for the characters to bet their items? I have yet to get one.

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up vote 9 down vote accepted

You do not need to do anything special in order for the characters to bet their special items. It is simply a random occurrence. When you start up a new game, instead of doing the $10,000 buy in, the character will offer their special item. So you could theoretically just keep trying to start games and quit.

Okay, just lost about $40k testing this, but I have a definitive answer now.

In order to restart the game several times without losing $10k each time, make sure you hit Escape to bring up the menu before the hand is actually dealt. If you do this while the opening cinematic about the buy-ins is still going (everyone tossing their cash in) then you will not lose $10k. As soon as you see 4 bundles of $10k hit the table (which means no special item), hit Escape quickly or else the hand will automatically be dealt and the game will save that you've lost $10k. If the camera pans to someone during the buy-in cinematic, that means that they don't have the money and will add their special item that you can get.

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Does this take $10,000 from your total each time? –  Ronan Forman Nov 28 '10 at 14:41
    
@Ronan: Not if you exit soon enough. Editing answer to reflect this. –  FAE Nov 28 '10 at 16:19
    
+1 - In know it's not a real $40K that you've lost, but 10 points is some compensation ;) –  ChrisF Nov 28 '10 at 16:36
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Thank I just used this to get the treasure hunt achievement! –  Ronan Forman Dec 7 '10 at 17:40
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