The amount allowed to borrow in each round at the table is based in how high the gambling skill is the higher the skill the more is allowed to borrow. When the player runs out of money (having $0), the player can borrow money from the casino when playing at a casino table (an amount of borrowed money corresponds with the player's wager on the table), leading to a negative money value. There are certain activities that bar the player from playing due to a low gambling skill, such as the Wheel of Fortune, which only allows those who could at least wager a maximum of $10,000. The skill increases by 1 for every $1,000 spent up to a maximum skill of 1000. In GTA San Andreas, the player can increase the gambling skill of Carl Johnson by spending money at the casinos.

With its expansion in GTA San Andreas the chances of losing/winning are more probable.

In Grand Theft Auto: San Andreas, more activities were available that the player can take part in to wager money on in order to gain more money if the player wins the activity or lose the money wagered if the player loses the activity. The ability to wager money is first introduced in Grand Theft Auto: Vice City, when the player must pay entrance fees for Vice Street Racer events, with a set limit on how much they can bet, and perform well enough in the races to break even.

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