Tough Nuts: Australia's Hardest Criminals

Brutal killer, armed robber, heart-breaker and prison escapologist, Ray was the ultimate anti-hero who spent his whole life running from the nightmares in his head. Denning’s cards were marked when he was just ten years of age. After many years of terrible domestic violence, his mother committed suicide in the family home by setting herself alight. Ray was found trying to quench the flames. With his teenage years spent on the streets and in and out of reformatories, Denning drifted into a life of crime. But whereas most boys his age were involved in petty theft or stealing cars, Ray Denning became an armed robber at 18 years of age. Caught by police and sentenced to 13 years in prison, Denning tried to escape from Parramatta Jail. During the escape attempt, Denning bashed a prison guard almost to death with a claw hammer. The prison guard, Willy Faber was so terribly wounded that he later died of his injuries, but as he died over a year after the attack Denning could never be charged with murder. Sent to Grafton Jail, one of the toughest prisons in Australia, Denning became politicised and started campaigning for prison reform. He also became the only man in history to escape from its walls. After his escape from Grafton Jail, he fled to Sydney where he conducted a high profile campaign for prison reform. Denning was a serial escapologist, who also escaped from Maitland and Goulburn Prisons, and spent over two decades in prison or on the run before stunning police and criminals alike when he rolled over to avoid a life in jail.