Gangland Australia · Episode 3 of 8

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

12 min · Free to watch

Graham Henry and Arthur "Neddy" Smith were two of Sydney's most infamous and feared gangsters through the 1970s, 80s and 90s, as feared behind bars as on the streets. They were friends and partners, until two contract killers arrived from Melbourne, Chris Flannery and Laurie Prendergast, and lit a match under an underworld that was already combustible. This first part of the story sets out who these men were before it all went wrong.

Henry opens the film himself. He was in organised crime, he says, from 1975 until 2010, and survived about 20 attempts on his life. Smith, he says, always got someone else to do it, and hired hitmen from Melbourne.

The six-inch punch

Henry was a career criminal shaped by a violent childhood. That toughness carried him from gang fights and running working girls to protection rackets, armed robberies and the drug trade. He never lost his punch. He had been taught a short, six-inch punch thrown with the whole shoulder, and it could drop the toughest men.

Johnny Regan found out. Regan was the top enforcer for Lenny McPherson, then the godfather of Sydney's underworld, and a deranged psychopath who allegedly killed his partner's baby out of jealousy. Henry says Regan came into a place where he was, touched him on the shoulder, and was knocked out cold with a right uppercut. Henry dragged him outside and gave him a kicking. When the police arrived, Henry says, he told them the man had said his name was Regan. The officer told him that was Johnny Regan, the one they called the Magician, because he made people disappear, and that he had killed seven or eight men. Henry has never told the story before, he says, because Mark "Chopper" Read claimed the fight for himself, and in Henry's account Read never fought Regan at all.

Regan's habit of appearing out of nowhere to unsettle McPherson, supposedly to expose weaknesses in his security, eventually wore out McPherson and his partner George Freeman. The film names Stan "the Man" Smith, sharper and smarter than Regan and the man called in when someone needed to disappear, as the one brought in to deal with the problem. In September 1974, after a day at the park with his girlfriend, Regan was dropped off in Marrickville and shot dead soon afterwards. Henry says that whoever did it should have got a medal. Regan was never going to make old bones.

Henry and Neddy

Smith, a tattooed giant of more than six foot five, and Henry became friendly in prison in the 1970s. Henry remembers Smith running things inside through size and fighting ability, a serious presence if not yet top tier. They met again by chance in a Sydney bar in the late 1970s.

Smith was not always trusted, and in some quarters he was hated. His prison sentence was for a gang sex assault on a woman, in which it is alleged he threatened her child. There were rumours that after an armed robbery went wrong he was beaten and turned informer under pressure from Roger Rogerson, the notorious corrupt detective. Smith denied all of it: he said he paid the police off and kept his mouth shut. Henry and his crew seemed content with his version.

Whatever the truth, the two were now a force, unbothered by the old heavyweights like Freeman and McPherson. They went full throttle into armed robberies and the drug trade, with, the film says, a green light from Rogerson. Despite Henry's private doubts about Smith, the money was good.

Rent-a-Kill

Christopher Dale Flannery was born in 1948 in Brunswick, in Melbourne. His alcoholic father vanished when he was nine. By 14 he was out of school, breaking into houses and stealing cars, and the courts sent him to Morning Star Boys Home, run by Franciscan monks and notorious for violent and sexual abuse. He had a giant Gothic cross tattooed across his back in the hope the monks would stop beating him. It did not work.

By his late teens he was in Pentridge's H Division, bashed and refusing to break. At 19 he was convicted, with his friend Laurie Prendergast, of sexually violating a woman, and got seven years. Out at 24, he worked briefly in the menswear department of David Jones in Perth, then took part in a robbery, was arrested in Sydney by Rogerson and sent back to Perth. In Fremantle jail, he said, guards tried to feed him to a feared enforcer. He picked up a dumbbell and nearly beat the man to death, and he later said that was when he knew violence was who he was.

Back in Melbourne in the late 1970s, he was skimming from Mickey's Disco in St Kilda. When its Sydney owners sent Ray "Lizard" Locksley to sort him out, Flannery allegedly killed him and sent back a bloodstained business card. People began to say Flannery was not right. There were rumours about his violence towards women. He called himself an international hitman; some called him a fantasist, and others feared he was exactly what he claimed.

By the time he reached Sydney, the film says, he had blood on his hands and an ego on fire. But Sydney had its own rules, set by crooked police like Rogerson and their favoured criminals, like Neddy Smith. Part two follows what happened when those rules met Flannery.

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