Naked City podcast: Rent-a-kill: Australia’s number one hitman

The Naked City podcast will take a journey into the dark depths of the Australian criminal underworld. In this series you will hear recordings of some of Australia's most dangerous criminals, all of whom have been remarkably frank in their recollections.

The man who made a profession out of hunting other humans Christopher Dale Flannery was not used to being the prey.

The hitman who moved to Sydney after being acquitted of the murder of Melbourne businessman Roger Wilson Flannery had run out of friends.

Christopher Flannery loved his work. When offered a contract he wouldn’t ask why – just how much.

For up to $50,000 he would kill and, as part of the service, he was usually prepared to dispose of the body.

In 1980 he took a contract from a white-collar gangster to kill a Melbourne businessman, Roger Wilson. Flannery and another man pretended to be detectives and, using a home-made police sign, pulled over Wilson’s green Porsche as he was heading home to his Nar Nar Goon property and his young family.

Christopher Dale Flannery (second from left) is led handcuffed into Melbourne’s City Watch House in October 1981 to be charged with the murder of Roger Wilson.Credit: Fairfax Archive

Flannery was acquitted of Wilson’s murder after Victoria’s then longest murder trial. The failure to find the body damaged the prosecution case.

A key Crown witness, Debbie Boundy, disappeared from a Melbourne hotel before she could give evidence. It is believed she suffered the same fate as Wilson.

After Flannery was acquitted, he was immediately arrested for the murder of Sydney underworld figure, Raymond Francis Locksley, in 1979.

After two trials he was acquitted.

Having been acquitted of two murders he had clearly committed, Flannery seemed to believe he was bullet proof. He made a living breaking the law – but then he decided to break the rules as well. He took a contract to murder a cop.

He attempted to murder undercover cop Mick Drury because the policeman refused a bribe to throw a trial against a drug dealer.

Out of control, a group of gangsters and crooked cops decided he had to go.

On May 9, 1985, he was last seen leaving an apartment building in Liverpool Street, where he was living. It was said he was heading to underworld boss George Freeman’s harbour-side home to road test a machine-gun. He didn’t know he would be on the wrong end of the barrel.

He was never seen again.