9. Nick Dandalos

Nick “The Greek” Dandalos, who was born into a rich family, immigrated to America at the age of 18. He quickly relocated from Chicago to Montreal, where he began to establish himself as a successful horse racing gambler. Nick went back to Chicago after earning more than $500,000 betting on horses, where he swiftly wasted all of his gains playing dice and card games.

Nevertheless, Dandalos continued to refine his casino gaming abilities and eventually became famous for his poker playing. Nick Dandalos is one of the most well-known gamblers in history since he frequently experienced financial success and failure, going from rags to riches. As for Nick, Over $500 million has been calculated as the total amount of his gambling winnings and losses.