Tough Nuts: Australia's Hardest Criminals

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, 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.

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.

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.