High Stakes Gambling is a Game Boy casino video game that takes place during the Great Depression in the 1930s.
A secret agent named Pete Rosetti, who is going undercover as an inteprid gambler, must turn the Mafia from filthy rich to dirt poor in a series of gambling games in order to arrest them.
The initial rounds of the game involve blackjack, poker and slot machines; with the final confrontation being done on five-card draw poker. For a price, players can also buy special cheating tools in the hopes of making a profit of the gangsters who often use cheating methods of their own. In the first round of the game, the player needs to raise his bank account to a quarter of a million dollars in order to defeat five Mafia members.
When running low on cash, the gangsters panic and increase the intensity of their cheat to regain their cash from the player. Machine Gun Max and Al Cologne (a parody of Al Capone) are just simply two of the gangsters that the player must defeat in high-stakes gambling.
Source: Wikipedia, "High Stakes Gambling", available under the CC-BY-SA License.