Tough Nuts: Australia's Hardest Criminals - Season 1

Christopher Dale Flannery earned the nickname of “Rentakill”. He was a hit man and gun for hire who would kill anyone if the price was right. TOUGH NUTS introduces the man who killed in cold blood before returning to his home to smother his children with affection and dote after his wife, Kathleen. In a TOUGH NUTS exclusive, we reveal Flannery ran a criminal enterprise, known as Rentakill Incorporated – a business not unlike the infamous Murder Incorporated in the mean streets of New York and Chicago in the 1920s and 1930s. Flannery did not act as a lone figure; he used as many as four accomplices to commit murder for money while establishing a sound alibi for himself. Nevertheless, Flannery killed as many as fourteen people by his own hand. The criminal feuds in place in Sydney and Melbourne offered Flannery and Rentakill Incorporated, with an almost endless array of victims. Through psychological profiling, we look into the mind of the hit man, Chris Flannery. Flannery grew up, the youngest of three children. His sister and brother became hard working and respected members of the community while Flannery turned to crime. The answer to Flannery’s violence is due in part to the nine years he spent in prison as a young man. Flannery was placed in the worst prison environment in Australia at the time – Melbourne’s Pentridge prison ‘H’ Division. Routinely bashed and sodomized by guards, Flannery went on a hunger strike. His action led to a parliamentary inquiry into conditions in ‘H’ and a number of prison guards were forced into retirement. Flannery emerged a hero to many prisoners. The brutalization he endured inured Flannery to the suffering of others. His prison experiences led him to become a killer for hire. Flannery moved to Sydney to face a murder charge in 1980 and from there he got caught up in whirlwind of criminal feuds. Feared by everyone in the Sydney crime scene, Flannery was a stumbling block to a lasting peace. He disappeared on May 9, 1985. He is presumed dead but his body has never been found.

Arguably Australia’s most feared gangster, Frederick ‘Chow’ Hayes was a convicted double murderer, sentenced to hang in 1952 for the brazen killing of standoverman and former boxer, Bobby Lee. Chow’s sentence was commuted to life in prison and he was released from jail in 1978. By this time, Chow was in the final decade of his life. At the time of his death, Chow had served almost 40 of his 74 years on the planet in jail. In his dotage, Chow became a celebrated crime figure – the subject of a biography by crime writer David Hickie and the subject of a chilling portrait by artist, Bill Leak that was short listed for the Archibald Prize in 1984. The portrait shows a wizened old man who still possessed the eyes of a killer. TOUGH NUTS charts the course of Chow’s life, from his formative years. Chow was the son of a WWI veteran; broken by his experience of the bloody conflict. Chow was nine years of age when he first set eyes on his father. His father was straight-jacketed in an asylum. Did this episode fuel Chow Hayes’ murderous rage, his complete lack of regard for humanity that saw him the most dreaded figure in Sydney’s underworld? Chow’s criminal career reads like a social history of the Sydney crime scene in the 20th Century – from the razor gangs of the 1930s, the post war booms in sly grogging, brothels and illegal gaming to the criminal networks founded on drugs.

Alphonse Gangitano was known as the Black Prince of Lygon Street and was the most lethal member of Melbourne’s notorious Carlton Crew in the 1980s and 1990s. Through a series of re-enactments of the most significant events in Gangitano’s life, TOUGH NUTS plots the rise and fall of the Melbourne crime tsar.

Dennis Allen was the oldest son of Melbourne crime matriarch, Kath Pettingill. While the remainder of her sons are criminals and some of them vicious killers, not one comes close to the utter brutality of Dennis Allen.

Meet Australia's most wanted man for a record 11 years. Russell 'Mad Dog' Cox was a man no prison could hold. He escaped from New South Wales' notorious 'electronic zoo', the maximum security Katingal jail - the jail the politicians had said was escape proof.

Michael 'Melbourne Mick' Sayers was a run of the mill crook who got in too deep with some of the tough nuts in Sydney's organized crime scene. An associate and friend of Chris Flannery, Sayers ventured to Sydney and discovered that to survive on the mean streets, he had to turn his hand to drug dealing, extortion, race rigging and murder.

Raymond 'Ray Chuck' Bennett was Australia's criminal mastermind. A brazen armed robber and thief, he did the jobs that other criminals considered were beyond them. His most audacious robbery was The Great Bookie Robbery - a heist at the Australian Jockey Club while the bookies met to settle up from the weekend's trade.

Lennie McPherson ruled the Sydney crime scene for four decades. He was a violent and vicious criminal and arguably the worst of the worst. Trace the rise and fall of Lennie McPherson from a street crook in the 1940s to the Mr. Big of the organized crime scene in Australia and to his death behind bars.