Tough Nuts: Australia's Hardest Criminals

- Season 2

(2011)

Radev invaded the lives of his extortion victims and terrorized them until they met his demands. Children, wives, family members were dragged in to his world of violence and horror. No one was safe.

Stan "The Man" Smith was a feared enforcer for the underworld of Sydney. He was George Freeman's right-hand man, a cold-hearted assassin, drug trafficker and murderer who turned into a man of God.

Brutal killer, armed robber, heartbreaker and prison escapologist, Ray was the ultimate anti-hero who spent his whole life running from the nightmares in his head.

Tilly was a drug dealing brothel madam, a criminal sociopath and Sydney's Queen of vice, who clawed her way to the top of the city's sex trade with a razor in her hand. Tilly Devine was a prostitute who founded a criminal empire on the mean streets of Sydney after the First World War.

Criminal lunatic, gunman, arch-thief and armed robber, Jockey Smith terrorized Australia at gunpoint for three decades. When confronted, the short angry guy with a bad case of small man syndrome invariably reached for a gun.

Multiple murderer, drug dealer, kidnapper, extortionist and street hoon, Dino Dibra grew up in Sunshine - a tough working class suburb where he became lifelong friends with a group of boys at school who would all go on to make their marks in Melbourne's underworld.

Multiple murderer, extortionist, pimp, child killer and violent thug, Regan is arguably the most violent and terrifying person in Australian criminal history. A genuine psychopath, Regan spent his childhood in rural New South Wales torturing animals.

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.