Gambling is a deep-rooted Cuban tradition. There were a lot of Casinos and gambling places in Cuba before the revolution. Castro eliminate all of them, and made illegal all types of Casinos and gambling, as well as the lottery. He viewed gambling and other "sin industries" as a criminal waste of the nation's financial resources.
Before 1959 you could bet on cockfighting, jai alai, horse racing or frequent casinos run by the American mafia and gangsters like the Jewish mobster Myer Lansky. Lansky brought to Cuba the biggest gamblers from Las Vegas, Reno and New York. The character Hyman Roth in "The Godfather Part II" is based on Lansky. For thirty years the mob had a presence in pre-revolutionary Cuba.
Presently, there is no form of legalized gambling or betting as existed in the pre-Castro days. There is, however, a form of underground lottery. Cuba’s illegal lottery is called la bolita, next to cockfights, is the most popular illegal game on the island. Tight-knit bolita networks, as in any efficient criminal enterprise, stake out turf across Cuba; big cities such as Havana and Santiago are divvied up among many (no one knows the exact number) self-contained operations. Everyday Cubans place their bets clandestinely with a listero or type of bookie. Since there is no longer an official Cuban lottery, winning numbers come from abroad. The last two digits of the five-digit Venezuelan lottery become the winning numbers in Cuba.