6. Archie Karas

Many people regard Archie Karas as one of the greatest gamblers in history. He is renowned for The Run, the longest and largest proven winning streak in casino gaming history. In December 1992, Karas traveled to Las Vegas with just $50 and went on to convert it into millions by winning $40 million by the start of 1995. The next year, the high-stakes gambler lost everything.

An old poker pal loaned him $10,000 to increase his $50 bankroll. At the poker tables, he quickly made enough money to pay off his debt. Karas’ illustrious winning streak came to an end in 1995, as all good things eventually come to an end. He lost the $40 million, all his earnings over the subsequent year while playing high stakes baccarat, craps, and poker.