Walters started gambling when he was 9 years old, when he bet the money he earned from his paper route on the
New York Yankees to beat the
Brooklyn Dodgers in the
1955 World Series. The Dodgers won and Walters lost the bet, but it did not deter him from gambling. Walters was a losing gambler as late as 1982. He had lost $50,000 by the time he was 22. Walters once lost his house during a game of
pitching pennies. The winner did not take possession; Walters agreed to pay off the debt over the next 18 months. Walters's success changed in his mid to late 30s. In June 1986, Walters requested a freeze-out with
Caesars Atlantic City for $2 million at the roulette tables. Walters was known to have lost $1 million at least twice at the
Las Vegas blackjack tables. Caesars, however, declined his request. Walters then took his proposition to the
Atlantic Club Casino Hotel, then known as the Golden Nugget, which was accepted. Walters and his gambling partner delivered $2 million to the cage at the Atlantic Club Casino Hotel. The pair noticed a wheel bias and bet on the 7–10–20–27–36. After 38 hours of play they won $3,800,000, beating the prior record of $1,280,000 held by Richard W. Jarecki at the San Remo Casino in
Monte Carlo in 1971. Three years later his "Syndicate" had won $400,000 at a casino in Las Vegas and an additional $610,000 from
Claridge Casino in Atlantic City.
Sports betting In the 1980s, Walters joined the Computer Group, which used computer analysis to analyze sports outcomes. Over a period of 39 years, Walters had only one losing year, with a 30-year winning streak. Though he has finished with a loss for a few months, he was always in profit by the end of the year. Walters bet on basketball, the
NFL, and college football. Walters won $3.5 million on
Super Bowl XLIV after betting on the
New Orleans Saints. Due to his reputation, Walters often placed bets through "runners" so bookmakers would remain unaware of the person behind the bet. Walters has admitted that he "only" wins about 57% of his bets, contrary to many sports betting "touts" who sell their picks by claiming much higher win percentages, and that he has been able to amass a fortune by betting on a huge number of games where he has a relatively small edge. In January 2007, Walters won a $2.2 million bet on
University of Southern California defeating
University of Michigan; USC won, 32–18. In 2011, Walters claimed he could make between $50 and $60 million on a good year. His plaque reads: "Billy Walters is known for being the greatest sports bettor of all time. He commands respect from every prominent bookmaker in the world and is known for contributing as a philanthropist to many causes." == Book ==