By early 1985 hitman Chris Flannery was running out of friends. This was hardly surprising, as he’d killed most of them. Flannery had built a fearsome reputation for killing on command but when an attack dog begins to snarl at its master it is time for the big sleep. Flannery’s boss Sydney gangster George Freeman had lost patience with him and was a little frightened of the unpredictable gunman. Flannery had threatened police and had shot one – undercover detective Mick Drury. Even in corrupt Sydney that was a crime that couldn’t go unanswered. He killed gangsters, shot dead a law-abiding Melbourne businessman, stabbed a major banking figure and orchestrated the murder of a teenage girl who could have given evidence against him. The man they called Rent-a-Kill made sure most of his victims were never found and that proved to be his fate when he was ambushed and murdered. He was no great loss. Become a subscriber: our supporters power our newsrooms and are critical for the sustainability of news coverage. Becoming a subscriber also gets you exclusive behind-the-scenes content and invitations to special events. Click on the links to subscribe https://subscribe.theage.com.au/ or https://subscribe.smh.com.au/ See omnystudio.com/listener for privacy information.