8. Bill Benter

One of the all-time richest gamblers is Bill Benter. A maths teacher by profession, Benter practiced his mathematical abilities at Las Vegas casinos in the 1970s by playing blackjack. Benter developed the card counting techniques outlined in Edward O. Thorp’s book, Beat the Dealer, and became a prominent professional blackjack player. He associated with Alan Woods and went on to create one of the most lucrative analyzing betting computer programs for horses-race betting.

Benter was able to make accurate predictions about the results of horse racing events by analyzing and taking into account no fewer than sixteen variables. He can reportedly win $5 to $10 million in horse racing wagers in a single day. It was also said that Benter uses his powerful software algorithm to make an estimated $100 million in betting each year.