Self made money making genius, Bill Benter, famed for his ability in Blackjack, and his prowess in betting on the horses studied physics at the University of Pennsylvania to improve his capabilities. Nor did he have ambitions in casinos, but managed to master card counting through Edward Thorp’s book “Beat the Dealer”, to win thousands in Blackjack. Four years later in 1984, Benter partnered with another gambler and mathematician named Alan Woods that translated to golden years of horse race betting in Hong Kong through their computers’ data. In Hong Kong horse racing is one of the legal vices together with football betting and the Mark Six Lottery, and it is monopolized by the Hong Kong Jockey Club that regulates Sha Tin and Happy Valley racetracks. Benter has an estimated wealth of $1 billion and it is believed he earns approximately $100 million in a year from sports betting with the help of the software that is developed to factor more than 130 variables.

Andrew Black’s experience started in computer programming and then moved to professional betting where he devised a unique approach of placing large bets on horse racing. After a brief stint at a London derivatives firm after his brother’s death, Black got back to betting and started a software firm. There he met Edward Wray, another Bridge lover, who found intriguing potential in Black’s algorithm that could predict the outcomes of horse races. It is through their partnership that they came up with Betfair, an online betting exchange which has now expanded to be among the best earning online casinos thereby increasing the US Sports Betting revenue which in 2023 was recording $1.55 billion. Betfair Casino stands out as the largest and the most popular betting exchange globally with more than 5 million trades in a day and as many as 1+ million customers. It is also known for delivering Crash Gambling and other new generation games, and therefore, strengthening its presence in the online casino markets segment.

One of the most famous bettors Alan Woods, Australian professional gambler, with Bill Benter used to make a great deal of money out of horse race betting in Hong Kong. Before that, Woods began his gambling career as a skilled card counter and a Blackjack player but after meeting Benter in Las Vegas, he switched to horse racing and sports betting. Woods, well-known for his analytical approach, successfully participated in sports betting with a mission of constantly developing new methods to outwit the existing strategies. One interesting feature about horse racing is brought about by Fusaichi Pegasus, which is the most expensive horse sold. Purchased for $4 million as a yearling, its value soared to $70 million following its Kentucky Derby victor feat, epitomizing the high risk and handsome rewards that defined Woods successful career.

Originally from Serbia, Zeljko Ranogajec, or The Joker as he is known in the gambling world, has accumulated a great sum of money relative to a great many of gambling activities including Keno, Blackjack, Bet on sports, and most peculiar horse racing. His unrivaled calculating skills in combination with the knowledge of work in bank, financial and taxation specialties together with experience in casino helped him home the method of card counting when playing Blackjack. California No Bust, along with Surrender Rules added to Ranogajec’s gambling experience in which he managed to improve his Blackjack expertise. Due to his deftness, he found himself blacklisted in some of the biggest casinos both in Australia, and Vegas. Together with Alan Woods, just like Bill Benter he used great mathematics to beat casinos. Although Keno came with small chances of winning, Ranogajec won $7.5 million in a casino in New South Wales, which influenced gambling tremendously.

Billy Walters, an American businessperson and now a retired professional gambler is renowned for his record-breaking performance in sports betting. Billy Walters was born in Munfordville, Kentucky in 1946 and at a tender age of nine, he began gambling and in his early years of betting he lost all his savings on one bet and later experienced several years of misfortune with the sports However, Walters faced the first of many obstacles throughout 2006 and 2007 but then achieved his greatest success in 2010; he won $3.5 million by betting on Super Bowl XLIV which was viewed by over 106.5 million people. For the first twenty years of gambling, Walters only enjoyed moderate levels of success; it was not until he was able to devise an efficient sports betting system that he was able to warrant losses in only one year of the last thirty nine, whilst using the gambling realm.

Terrance Watanabe took over the Oriental Trading Company from his father and this business emphasized selling arts and crafts, party supplies and resources, school stationery and toys. In 2000, he decided to let the Company go as he pursued his passion in playing Baccarat, Roulette and Blackjack well. After a short time Watanabe was unable to pay his debt for enormous losses in gambling in the Wynn and Caesars Palace, two casinos that contributed largely for the development of the Las Vegas Strip. He was lavishing and by the year 2007 had reached a record of a colossal loss streak in Las Vegas, losing $827 million out of which $127 million was a record loss in the history of Las Vegas. It was made worse by the fact that he had an outstanding balance of $14.7 million that he owed to Caesars Entertainment, a fact that he disputed saying that they never refunded him 30% on his losses.