Tough Nuts: Australia's Hardest Criminals

Murderer, standover man, race fixer, SP bookmaker, and crime lord, George Freeman was the King of Sydney for over three decades. His skills as a gambler and race fixer meant he could enrich his associates and a growing band of influential people who helped keep him out of trouble with police. Freeman grew up on the tough streets of Annandale and fell into crime at an early age. A product of boys’ reformatories like Mt Penang in Gosford, Freeman was a small waif like child, and suffered the worst imaginable treatment. His response to the terrors of his childhood was a seething violence that remained with him until his middle years. Approached by Sydney’s Mr Big, Lennie McPherson, Freeman dropped his life of property crime and began concentrating on illegal gambling at McPherson’s behest. Freeman rapidly became one of Sydney’s most influential criminals, running a network of SP bookies and standing over the illegal casinos for protection money. Freeman, together with McPherson and Stan “The Man” Smith formed a criminal alliance known as The Team. While Freeman fronted as The Team’s gambling heavyweight, he was not above committing murder to entrench The Team’s dominance in the Sydney underworld. When the madman, Stewart John “The Magician” Regan loomed as a threat, it was Freeman and Tough Nut Stan ‘The Man’ Smith who did the shooting. A decade later, Freeman and Smith would join forces again, this time to dispatch the loose cannon, hit man, Christopher Dale “Rentakill” Flannery. In 1979 and at the height of his powers, Freeman faced an assassin’s bullet but lived to tell the tale and exact revenge. Muller had a grudge against Freeman, and shot him in the neck and face outside the front door of his mansion at Yowie Bay with .22 handgun. The gangster kingpin took a contract on Muller’s life, and within six weeks Muller was shot dead. In his dotage, Freeman, a chronic asthmatic, became addicted to pethidine, and the King of Sydney died prematurely as a result of his addiction.