 Waterhouse became a barrister in 1948 but took leave of absence in 1954 after the sudden death of his brother and partner, Charles, and never returned, making bookmaking his full-time career.He worked his way on to the 'rails' (the Australian higher-class, higher-stake betting ring at a racetrack, as compared to bookmakers of the 'paddock'), and rose to be reputed the world’s biggest bookmaker and gambler in 1968.He engaged in betting duels with giant punters such as Frank Duval (Hong Kong Tiger), Filipe Ismael (The Filipino Fireball) and Ray Hopkins.