William Hollebone was born at St Peters, New South Wales in 1917. His mother died when he was eight years old and by then he was deemed by the courts as an uncontrollable child and spent much of his childhood in boy/youth reformatories. At the age of 18, he and two associates were involved in a gang assault of man named Leslie Archibald Hobson in King StreetNewtown, New South Wales. The three attackers kicked Hobson to death in the street, but at trial it was perceived that Hobson died when his head hit the concrete pavement. This allowed Hollebone and his gang to accept a lesser charge of manslaughter and the three were sentenced to 10 years' imprisonment on 29 November 1935.
War years and Waterloo shooting rampage
Hollebone was released in late 1943. He married Hazel Jean Ryan in early 1944, and lived in Surry Hills, New South Wales. At around this time he also teamed up with John 'Chow' Hayes and the two of them set out to become the two most feared Sydney criminals of the 1940s. He and Hayes were involved in extortion, theft and intimidation on a scale that Sydney's police force had rarely seen since the Razor gang wars of the late 1920s. Hayes and Hollebone were both instrumental in large scale black-market tobacco scams during the later part of World War II, which made them wealthy at the expense of many deceived customers. Greed destroyed their black market scams when one of their gang, a man named Eddie Weyman, stole a considerable amount of the gang's profit. In a swift show of retribution, Hayes shot Weyman dead on New Year's Eve 1945. Hollebone was always known to carry firearms, and was a man not to messed with. He was an alcoholic with a vile temper, and was incarcerated again for six months in 1944 on a firearms possession charge. During this short stay in prison, Hollebone learned that his wife had left him for a small-time criminal named Alfred Frederick William Dawes of Waterloo, New South Wales. Upon his release from prison, Hollebone decided to enact revenge on Dawes, and visited Dawes' home on the evening of 29 August 1946. Upon entering the premises, Hollebone fired seven shots from his revolver, killing three people including Dawes and injuring two others. Hollebone was charged with the triple murder. An Inquest was held into the incident at the City Coroner's Court on 10 October 1946, and many of the witnesses refused to implicate or even identify Hollebone as the killer, which frustrated the police and the judicial system to such an extent that Hollebone was later found not guilty due to lack of evidence. Hollebone's wife wasn't to be left out either. Hollebone and his wife Hazel were arguing at his Reservoir Street home one night in 1946 when Hollebone decided to stab his wife in the face with a broken beer glass, an injury that required over 50 stitches. She later divorced him.
Late 1940s
Hollebone began working with Hayes exclusively from 1947, in various criminal activities. He and Hayes were also employed as a debt collectors for Joe Taylor of Thommo's Two Up school, although the pair were often too drunk to be of much use to Taylor, but the pair of them aggressively continued their extortion scams which terrified Sydney residents and criminals alike. Both Hollebone and Hayes were gaoled in 1948 for home invasion and the extortion of Phillip And Adelaide Great and family of Surry Hills, New South Wales and were released in early 1950.
1950–1960
By 1950, Hayes and Hollebone were the most feared gunmen in Sydney. Hollebone was with Hayes when he shot William 'Bobby' Lee at a Sydney nightclub on 29 May 1951, although Hollebone was later acquitted of involvement on 29 August 1951. After Hayes received his 15-year jail sentence for killing Lee, Hollebone continued on as a one-man "crime wave" in Sydney, and he was shot several times by 'unknown' assailants. Hollebone was again gaoled for two years in March 1954 for possession of a firearm back in October 1953. The trial judge described him to the jury as "a man who had previously been charged with consorting with criminals, one charge of manslaughter and two previous charges of carrying firearms." Police described him as "an associate of the worst type of criminals". He continued to associate with dangerous criminals, including a young Lenny McPherson. As he became older, his alcoholism worsened and he became an even greater risk to the community. He was sent to prison on numerous later occasions, and had a price put on his head by a newer breed of Sydney criminals who wanted him assassinated, but he died of natural causes before that ever happened. Hollebone died in Darlinghurst, New South Wales on 28 September 1960 from a cerebral hemorrhage, aged 43.
