Born in Myrtle Point, Oregon in 1948, he became a chess master and backgammon player but eventually opted to pursue a career in professional poker. As it turned out, it was a good decision because he has always been successful in the poker world.
Waterman attributes his success in poker to reality and experience saying that although reading poker books and watching poker games on television or in casinos helps a lot in augmenting the people's knowledge of the game of poker, they will never succeed unless they try playing the game themselves. He says that reading and watching are entirely different from actually playing. But like chess players, Waterman likes to watch and play against famous poker players because he admires the strategies they use at poker tables.
The first time Waterman became recognized as a major poker player was when he attended the 29th Annual World Series of Poker in 1998 where he finished in the money and poker has made Waterman a millionaire; he has won over one million dollars in poker tournaments.
Waterman, an elusive figure on a quest for enlightenment, describes himself as a hologram from hundreds of previous lives as a Buddhist monk. He's a man of nature, a former logger who lived in seclusion deep in the Oregon forests. Born and raised in Oregon, Waterman became a logger at the age of 13. As a teen he excelled at strategy games, playing backgammon and chess when bad weather kept him from logging.
He was a good enough chess player to have won the Brilliancy Prize at the 1973 American Open and it was during that time that he had a ‘spiritual awakening’ and studied subconscious visions. He eventually experienced a ‘lucid dream’ while at a tournament in Lone Pine in which three men in the dream told him they would provide him with spiritual guidance as well as teach him about the physical reality in which humans live, ancient languages and how to survive natural disasters. As a result, Waterman has written extensively about his meetings with the men in an online series entitled, "Knowledge from the Ancient Cave."
Losing interest in chess, he quit playing in 1975 and returned to Oregon to work as a logger, but a prominent U.S. businessman had read a chess profile of Waterman in the Los Angeles Times and decided to track him down. After about a year of searching, Waterman was located in the Oregon woods where he was without a phone or any connection to the outside world. The businessman offered him a membership with the Chicago Board of Trade, $2 million in wages, a $10 million line of credit and a regular job. Waterman accepted the opportunity and worked as a corporate troubleshooter in Chicago before relocating to New York to work in finance.
By that time, he had turned to backgammon as his game of choice but managed to fit in some poker tournaments on the side. Eventually he quit both business and backgammon and embarked on a career as a professional poker player.
Waterman made his mark in poker in 1998 when he began popping up at poker tournaments and doing well by winning minor events. Then, in 2002, he scored his first major tournament win: first-place in the Los Angeles Poker Classic in Pot-Limit Hold'em and subsequently he played in two World Series of Poker finals taking fifth in the $1,500 Pot-Limit Hold'em event and eighth in the $3,000 Pot-Limit Hold'em event. In 2002 at the Bellagio Five Diamond Poker Classic No-Limit Hold'em table Waterman won over $100,000 and that was only the beginning. He has won more than 180 poker tournaments.