George David Freeman (1935-1990), criminal, gambler and racing commission agent, was born on 22 January 1935 at Annandale, Sydney, third child of William David Freeman, builders’ assistant, and his wife Rita Eileen, née Cook. George had a disturbed and hard upbringing. After the departure of his father from the family, George's mother remarried a man with a criminal history. Unfortunately, this individual passed away shortly after the marriage. As a result, George's mother faced significant challenges in raising her three children in a small, two-bedroom apartment located in a disadvantaged area. ‘Food was bread and dripping, chips, treacle, stuff like that’. Expelled from two schools, at 12 he was arrested for stealing and put on two years’ probation. Upon leaving Glebe Junior Technical School at the age of 14, he spent approximately two years employed as a stable-boy. During this time, he frequented poolrooms, engaging in hustling activities to acquire money. Unfortunately, this led him down a path of criminal behaviour.

Convictions for breaking and entering, car stealing and a smash-and-grab raid resulted in a sentence of two years in Mount Penang Training School, Gosford, in 1951. Transferred for continual misbehaviour to the notorious Tamworth Boys’ Home, he swallowed soap to make himself sick in the hope of a transfer. When the prison doctor diagnosed his condition as acute appendicitis, he was forced to have an unnecessary operation. To tell the truth would have meant a severe beating from the guards.

`With a new suit, five bob and a train pass to Sydney’, Freeman was released in January 1953. Next year he was sentenced for stealing and in Parramatta gaol met his boyhood hero, the prison escapee Darcy Dugan. On release he worked at the State Abattoirs at Homebush, but further gaol terms, usually for petty theft, followed. He married Marcia Bedford, née McDonald, a divorcee, on 5 February 1963 at the registrar general’s office, Sydney. In 1968 he served his last gaol term, in Fremantle, Western Australia. With his boyhood friend Stanley (`The Man’) Smith, he went on a false passport to visit the United States of America as a guest of an acquaintance, Joe Testa, an alleged member of a crime syndicate interested in infiltrating Australia. When Testa visited Sydney in 1969 and 1971 Freeman renewed his association with him.

For the next twenty years Freeman concentrated on the racing industry, working as a commission agent and illegal off-course betting operator and becoming one of the most talked-about alleged leaders of organised crime in the State during a time of corrupt police and politicians. In June 1971 he was said to have been part of a syndicate that broke the Canberra Totalisator Agency Board jackpot with a win of $500,000. In 1973, examined before the royal commission into organised crime in clubs in New South Wales (chaired by Athol Moffitt), Freeman denied on oath that he was involved. It was alleged that in June 1976 he was part of, or supportive of, the `Taiping conspiracy’—a plan, hatched in a Chinese restaurant, to bribe politicians in order to gain control of a proposed casino board.

In 1978 Freeman was detained in the USA as an `excludable person’ and named in the New South Wales parliament as an organised-crime figure. That same year he bought a palatial waterfront mansion at Yowie Bay, Port Hacking, protected by high walls, security cameras and guard dogs. In 1979 a police intelligence report on him, tabled in parliament, alleged that he was heavily implicated in illegal off-course betting. On 25 April Freeman was shot in the neck by an unknown assailant, but survived. He was also named as a `crime boss’ in P. M. Woodward’s royal commission on drug-trafficking. Divorced in 1977, on 6 August 1981 Freeman married 24-year-old Georgina Catherine McLoughlin, an orthoptist and a former actress and model, at St Stephen’s Uniting Church, Sydney.

Accused of murder, assault, fixing horse races (as in the `Mr Digby’ affair), running illegal casinos, bribing police and dealing with American crime figures, Freeman featured in Sir Laurence Street’s royal commission into committal proceedings against K. E. Humphreys (1983) and in D. G. Stewart’s royal commission into alleged telephone inter­ceptions (1985). But Freeman’s only convictions, in 1983 and 1986, were for illegal betting, for which he was fined $500 and $5000 respectively. Freeman was considered the main player in the 'Fine Cotton' ring-in affair, along with Bill Waterhouse in 1984 and was said to virtually control who won and lost at the Harold Park trots every week for a long period. His tentacles spread from harness racing through the galloping game and reached out to corrupt dirty cops, racing officals, trainers and jockeys. Horses were shot, racing people were beaten up and bribed, with one jockey claiming he was paid $5000 to stay out of the top three in a race. Because of his record he and his wife were barred from enter­ing Britain in 1985.

Freeman, 5 ft 8½ ins (174 cm) tall, handsome, white-haired and tattooed, was a smart dresser. Described by a police source as ‘hard, smart and charming’, he had a certain degree of social acceptability despite his reputation. In 1988, admitting that he had been ‘right in the guts of Sydney’s underworld, in tough and controversial times’, he took the unusual step of publishing an Autobiography. An apologia for his life, it relates frankly and movingly his youthful drift into crime, but is somewhat less satisfying on his later life. Often portrayed as a charming celebrity gangster, he was in fact a calculated criminal motivated by greed and a lust for power and influence. One of Sydney's most notorious and unforgiving hard men, Freeman preferred others to do his dirty work. He dominated that city's underworld alongside Lennie McPherson, controlling a vast illegal gambling empire while keeping top cops, judges and politicians in his pocket. In poor health for some years with asthma and kidney disease, and addicted to the painkiller pethidine, Freeman died of asthma in Sutherland Hospital, Caringbah, on 20 March 1990 and was buried in Waverley cemetery.

Destined for a life of crime, George Freeman would rise to the Top of the criminal underworld in Sydney