As a teenager he was hired by a local saloon to watch over games and make sure they were played honest. While he was maintenance games safe from cheaters, he was also learning the strategy behind playing poker. Two years later he became a rounder, a player that travels the country looking for gambling proceedings. In 1949 Moss once played with Nick the Greek in a five month long poker marathon set up by Benny Binion, winning somewhere from $2 million to $4 million. Since of public like Nick the Greek, Binion and Moss, poker became well loved and eventually a World Series of Poker was organized. Moss won the 1970, 1971, and 1974 World Series of Poker main events, tying him with Stu Ungar for the most WSOP main event titles. For the 1970 event, Moss was really elected the champion by his peers and only received a silver cup as his prize. He played at every WSOP from 1970 to 1995 and during his career he won 8 WSOP bracelets and over $680,000 in tournament play.