2. Billy Walters

One of the most well-known sports gamblers in history is Billy Walters. He also has the longest winning streak of any sports bettor in Las Vegas, spanning over 30 years. When Walters was nine years old, he began gambling by risking (and losing) the revenue from his paper round on the 1955 World Series.

As Walters wagered, his poor luck persisted, and by the time he was 22, he had apparently lost $50,000. But by the time he was in his late 30s, his luck had massively improved. Walters, though, is one of the most well-known gamblers in history, thanks to sports betting. His two largest winnings were $2.2 million on a college football game and $3.5 million on Super Bowl XLIV.