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. Freeman grew up on the tough streets of Annandale and fell into crime at an early age. A product of boys’ reformatories like Mt Penang in Gosford, Freeman was a small waif like child, and suffered the worst imaginable treatment. His response to the terrors of his childhood was a seething violence that remained with him until his middle years. Approached by Sydney’s Mr Big, Lennie McPherson, Freeman dropped his life of property crime and began concentrating on illegal gambling at McPherson’s behest. Freeman rapidly became one of Sydney’s most influential criminals, running a network of SP bookies and standing over the illegal casinos for protection money. Freeman, together with McPherson and Stan “The Man” Smith formed a criminal alliance known as The Team. While Freeman fronted as The Team’s gambling heavyweight, he was not above committing murder to entrench The Team’s dominance in the Sydney underworld. When the madman, Stewart John “The Magician” Regan loomed as a threat, it was Freeman and Tough Nut Stan ‘The Man’ Smith who did the shooting. A decade later, Freeman and Smith would join forces again, this time to dispatch the loose cannon, hit man, Christopher Dale “Rentakill” Flannery. In 1979 and at the height of his powers, Freeman faced an assassin’s bullet but lived to tell the tale and exact revenge. Muller had a grudge against Freeman, and shot him in the neck and face outside the front door of his mansion at Yowie Bay with .22 handgun. The gangster kingpin took a contract on Muller’s life, and within six weeks Muller was shot dead. In his dotage, Freeman, a chronic asthmatic, became addicted to pethidine, and the King of Sydney died prematurely as a result of his addiction.

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. After moving to Sydney, Regan became a pimp and recorded a conviction for living off the earnings of a prostitute. Over the years to come, Regan would control a string of prostitutes, running brothels and overseeing streetwalkers, controlling these vulnerable women through fear and violence. Regan soon committed his first murder; the body of his victim, like so many others to come, simply disappeared. Regan quickly assumed the identity of his given nickname – the Magician. He was the conjuror who would make associates and enemies alike vanish into thin air, never to be seen again… Regan despised the police. The only police officer Regan ever deferred to was a tough cop named Gil Mackie. Mackie had been a Kokoda veteran who had seen humanity at its worst. Knocked to the ground, Regan looked up and called Mackie “Sir”. The violent thug had been beaten down for the first time in his life. Regan’s most outrageous crime was the murder of a four-year-old boy, Karlos, the son of a girlfriend of Regan’s who had been left in his care. Karlos disappeared, and like so many of Regan’s victims his body has never been found. With that final killing Regan crossed a line. The police couldn’t tolerate a child-killer on the loose, and Sydney’s crime lords made the decision to dispose of him. Regan by that point was so out of control they knew that one day he could come after them, too. Regan was lured to a hotel in Marrickville on the pretext of a meeting with gambling king George Freeman. But Freeman was waiting with Stan “The Man” Smith – a feared assassin. Regan was shot by both men and left to die on the street, sending a message to criminals and police alike that justice had been done.

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. Dibra and his gang members, attired in the accoutrements of their violent lifestyle, would set upon their rivals, administering beatings during torture sessions in the garages of their parents’ modest suburban homes. The gang lived by a set of rules that would always be broken. And it was Dibra who broke them first. He fell out with Veniamin and Veniamin had the young gangster wannabe knee-capped with his trusty 9mm “toy”. Dibra recovered but the gang had torn themselves apart. He went on his own way, befriending the emerging king of the party drugs, Carl Williams. Dibra became a high-ranking distributor for Williams. With the position came wealth and influence and Dibra, the gangster with a reported IQ of 89, deluded himself into believing he would one day control the Melbourne underworld. He may not have been bright but Dibra was fearless to the point of recklessness. He refused to bow to Melbourne crime figure, “Mad Charlie” Hegyalji, waiting patiently in his front yard to shoot him dead one night as he returned home. Dibra, the gangster wannabe had become the real thing, and rapidly became renowned for spontaneous, almost pointless outbursts of violence. In one typical incident, Dibra and his mate Rocco Arico kidnapped Melbourne standover man Richard Mladenich and attempted to ransom him, only to be horribly disappointed that no one was interested in paying a ransom for him. Dibra, the star who shone brightly, was always set to burn out quickly. Dibra was finally murdered by his old schoolmate, Benji Veniamin, outside his shack in Sunshine West. The kid, who had always wanted to live like a gangster had finally achieved the death he would have wanted, gunned down in the street by a former friend. He was just 25.

Criminal lunatic, gunman, arch-thief and armed robber, Jockey Smith terrorised 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. In a TOUGH NUTS exclusive, we bring the first in depth interview with the policeman who finally brought Jockey’s one man crime spree to an end, shooting him dead in order to save his own life. Jockey did his criminal apprenticeship with Ronald Ryan - the last man to hang in Australia. Later on Jockey found his way to Pentridge as a prisoner but escaped after only two days by obtaining a visitor’s pass and casually walking out the front gate. Jockey lived his life on the run in plain view. Brazenly he returned to the life he always wished he’d had and worked in horse racing. The incorrigible criminal’s joke was to call himself Tommy Cummings, training horses under the names of the two great trainers of the time: Tommy Smith and Bart Cummings. After the largest manhunt in NSW history, Jockey was captured near his hideout in Nowra in 1977 and served 14 years in prison, convicted of armed robbery and attempted murder. Released in 1992, Jockey returned to crime. With police on his tail, Jockey did one last dramatic hold up at a suburban shopping centre on the NSW Central Coast. In a crime typical of his manic life, Jockey stole some worthless household goods from a shop. When confronted by store detectives, he pulled a gun, kidnapped two shoppers for good measure and fled the scene in a stolen car. The little man had again escalated a minor crime into abduction, kidnap and wild-eyed threats to kill. Jockey’s violent life came to an end a week later in rural Victoria when country policeman Ian Harris shot Smith dead in the car park of a hotel.

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. She established a network of brothels, enslaved her working girls on cocaine and slashed, bashed and shot her way to the top of the criminal tree in Australia. Growing up as a child prostitute in London, Tilly met Jim Devine, an Australian soldier during World War One. Tilly arrived in Sydney as a war bride in 1920, only to find Jim putting her back on the game again. After five years working the streets, Tilly began building a network of brothels around the Palmer Street area of Woolloomooloo in inner city Sydney, with the violent drunken thug Jim as her partner. When the men reached for their cutthroat razors in gang fights, which proliferated in the 1920s, Tilly did the same, slashing the face of any man who got in her way. Her propensity for violence and the impulsive bursts of rage never left her and Tilly remained a sea of explosive anger to the day of her death in 1970. Tilly survived two World Wars and the Great Depression and became incredibly wealthy from the proceeds of her sex and drug empire. Like the gangster Al Capone, Tilly’s empire collapsed when she was pulled up by the Tax Office and handed a fine of 20,000 pounds. Tilly was forced to liquidate everything, and lost her empire overnight. By the time of her death in 1970, Tilly had become an embarrassment; an historical anomaly, a ghastly monster of a past that the people of Sydney no longer cared to dwell upon.

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.

Feared enforcer for Australian organised crime; multiple murderer and assassin; and drug trafficker turned man of God. Smith was mentored by Sydney hard-man and ‘Mr Big’ Lenny McPherson. Together with George Freeman they founded notorious Sydney underworld gang The Team. With his steely nerves and violent nature, Smith naturally became The Team’s enforcer. Smith was also an accomplished assassin, and the man chosen to rid The Team of its greatest threats, including Chris Flannery and Stewart John Regan. Together The Team dominated Sydney’s underworld for over 30 years. Stan Smith also operated a venture on his own, becoming the biggest distributor of marijuana in eastern Australia. However in an ironic twist for the man who became rich importing drugs, his oldest son became a heroin addict and died of an overdose. Smith sought revenge by hunting down and murdering his son’s heroin dealer in the most gruesome way imaginable, repeatedly running over him in a car and leaving him to die. Despite his life of crime, Smith was a devoted family man. He married his wife, Marilyn when they were both just 18 years of age. They remained married until Smith’s death 54 years later. In a remarkable twist, towards the end of his life, Stan turned to God. In a television exclusive, Tough Nuts will screen footage of the born again Smith’s baptism, transforming the multiple murderer into a man of God.

Radev invaded the lives of his extortion victims and terrorised them until they met his demands. Children, wives, family members were dragged in to his world of violence and horror. No one was safe. Radev was a Bulgarian wrestler who came to Australia, claiming resident status as a political refugee. He preferred the nickname “The Russian” believing it instilled greater terror among his victims. Radev boasted of his close connections to the Russian mafia. Tough Nuts provides detailed accounts of Radev’s terror tactics from several of his victims. Businessman Sedat Ceylan was lured to a hotel room in Melbourne and viciously assaulted by Radev and his thugs for nine hours. Tough Nuts reveals that Radev committed identity theft and went on a crime spree, all under the name of his neighbour, a Russian émigré named Ivan Solokov, who he murdered. And for the first time on television, then police detective and former member of Victorian Police’s Organised Crime Squad, Ben Archbold tells of his terrifying confrontation with Radev. Radev was a psychopath; able to compartmentalise his life. He charmed and courted his wife Sylvia and had a daughter with her. He kept his wife and daughter, almost as goods and chattels in a separate home. The drop-in husband and father would call by on regular visits, kiss his daughter on the cheek and secrete guns and drugs in the child’s cot before heading back to his life of crime. On the blood soaked streets of Melbourne’s gangland war, the lethal Radev was deemed too dangerous to be allowed to live. His life was terminated at the demand of drug lord, Carl Williams with Williams’ devoted assassin, Andrew ‘Benji’ Veniamin the triggerman.