Gangland Australia · Episode 4 of 8

Gangland Sydney, Part 2: The Hitmen Who Vanished Without a Trace

15 min · Free to watch

Part one set out who these men were. Part two is about what happened when two Melbourne hitmen, Chris "Rent-a-Kill" Flannery and Laurie Prendergast, tried to live by their own rules in Sydney. Within a few years both had vanished, and no bodies were ever found.

Out of Melbourne

Prendergast's move to Sydney, the film says, was probably a wise one. In Melbourne he was caught up in a war with the Painters and Dockers and the Kane family. Les Kane, widely regarded as a violent psychopath, had been ambushed and executed at his home by an elite armed robbery crew, and according to Kane's wife Prendergast was among them. The feud grew out of the Great Bookie Robbery of 1976, which netted more than $17 million; Kane had allegedly tried to extort money from the gang behind it. In 1979 Raymond "Chuck" Bennett, the leader of Prendergast's crew, was shot dead in a courthouse. In the end every member of the Bennett gang but one would be dead.

Flannery was already in Sydney. Graham Henry met him in the early 1980s and was quietly warned by friends not to trust him. According to police, one of Flannery's first jobs was the murder of the barrister Roger Wilson. In August 1980 he and two other men were charged; police alleged they abducted Wilson and took him to Pakenham, where Flannery shot him. Wilson's body was never found, and all three were acquitted. As Flannery left court, New South Wales detectives charged him with the 1979 murder of Ray Locksley. The 1982 jury could not agree. Flannery avoided the April 1984 retrial with a medical certificate from a doctor who was later jailed for perverting the course of justice.

The barmaid

Flannery became bodyguard to George Freeman, one of Sydney's most powerful crime figures, but even Freeman could not rein him in. He fell in with Neddy Smith. At first Smith and Henry had discussed killing Flannery, having heard he was being paid to kill them. He reassured them, and he and Smith became close, drinking for hours and trying to outdo each other's stories of violence.

The break came when Flannery asked them to help kill Michael Drury, a detective who had refused dirty money from Flannery's associate Alan Williams. Henry was furious and refused. According to Henry, Smith was more receptive, and from then on, Henry says, Smith and Flannery conspired to kill him. When Henry went to collect money from Smith, it was a trap, but he had been warned and went in armed. Flannery was there. Henry says he had a gun between Flannery's eyes and was about to fire when a barmaid walked in. After that, he says, Prendergast and Flannery made several more attempts on his life. All of them failed.

Not a koala

By late 1984 the Sydney gangland war was raging. Smith later said Flannery was shooting at anyone he thought was connected to Barry McCann and Tom Domican. When a senior officer told him to settle down, Flannery told him he was not a protected species; he was not a koala. On 6 June 1984 Drury was shot in his home and survived. Williams later testified that he had offered $50,000 each to Flannery and the corrupt detective Roger Rogerson to kill him.

On 27 January 1985 someone sprayed Flannery's house with 30 bullets. He was hit in the hand shielding his wife. He blamed Domican, who was charged and later cleared. On 23 April 1985 Flannery was allegedly sent to kill Tony "Spaghetti" Eustace, who was found outside the airport Hilton, shot six times in the back, and died refusing to talk to police. By then Flannery was suspected of at least a dozen murders.

9 May 1985

He moved into a high-rise near police headquarters. Whispers said even Freeman was tiring of him. On 9 May 1985 Flannery was called to a meeting with Freeman. His car would not start, Freeman told him to get a cab, and he got out of it on Liverpool Street and was never seen again.

The theories are many: a hit ordered by Freeman, or Smith finally having had enough. Smith himself later claimed that on the day Flannery disappeared he saw him getting into a police car driven by a detective he knew well. In 1997 the New South Wales coroner Greg Glass ruled that Flannery was murdered on or around 9 May 1985, and called Rogerson the key to solving it. Rogerson told national television that Flannery was a pest who would not do as he was told, and had overstepped the line.

The ghost

Prendergast was the opposite: quiet, cold and calculating. He was rumoured to have been with Flannery on several jobs, and Henry says he was there when Henry was nearly set up. In the months after Flannery vanished, the film says, Prendergast began asking too many questions, pressing Smith and even Rogerson about what had happened and who had been in that police car.

What is known for sure is that Prendergast disappeared in Melbourne in 1987. His wife said he slept with a pistol under his pillow and knew his life was at risk. Whether it was Sydney cleaning up its business or old Melbourne vendettas, the film leaves open. Like Flannery, he left nothing behind but silence.

Previous: Gangland Sydney, Part 1: The 'Psycho' Hitmen Who Picked the Wrong City

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