1959: Through a Chapel Ventilator: the Sydney Jailbreak That Triggered Australia’s Biggest Manhunt
Kevin Simmonds and fellow inmate Leslie Newcombe escaped Sydney‘s Long Bay jail on 9 October 1959 by squeezing through a ventilator in an old chapel while prisoners watched a film. The next day they killed prison guard Cecil Mills at Emu Plains Prison Farm and fled with his gun, triggering what became the biggest manhunt in Australian history.
Newcombe was caught within a fortnight, but Simmonds evaded hundreds of armed police, tracker dogs and a helicopter for more than five weeks, tying up two rangers and stealing their truck along the way. Detective Sergeant Ray Kelly, nicknamed ‘Gunner’ for his record of shooting suspects, finally ran him down near Mulbring on 15 November, by which point crowds were cheering him at police stations as a folk hero.
A jury convicted both men of manslaughter rather than murder, and Simmonds was sent to the ‘intractables’ wing of Grafton gaol. Six years of brutal treatment there left him a vacant, self-harming shell of the man who had outrun the state; he was found hanged in his cell in 1966.
