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The City’s Fastest Hankie

During the Chicago-style spate of gangland killings in and around Sydney in the 1960s, none was more public that the execution of underworld psychopath turned hitman, Raymond Patrick ‘Ducky’ O’Connor.

At the time of his demise, the stocky 29-year-old ex-meat worker turned gun-for-hire had been implicated in a succession of gangland hits which included the machine-gun murder of Robert James ‘Pretty Boy’ Walker and the assassination of greyhound trainer Charlie Bourke, who copped 20 bullets in the back and neck from a .22 semi-automatic rifle on the front lawn of his home.

During the late 1960s O’Connor was standing over various Sydney gambling club operators whose illegal casinos were allowed to flourish under a corrupt Liberal state government and a police force that would make the politicians look like choir boys.

O’Connor had made it blatantly clear that if any of the police who were on the casino’s payrolls tried to stop him as he went about his business he would shoot them as soon as look at them. With threats like this Blind Freddy could have told you that it wouldn’t be too long before Ducky became a dead duck.

Fresh out of jail, O’Connor was on bail pending the hearing of a Melbourne murder charge against him when he entered Sammy Lee’s Latin Quarter nightclub in Pitt Street, in the heart of Sydney, at 3.20 am on 28 May 1967.

The club was closing and about 50 people were having their last drinks at their dimly lit tables as they prepared to rug up and go out into the chilly autumn morning.

No sooner had O’Connor sat down at a table occupied by three men than a single shot rang out and he slumped to the floor. There was a mad rush for the door, and within no time the only people left in the club were some staff hiding behind the bar, the three men at O’Connor’s table and two detective sergeants who just happened to be drinking at a table nearby.

One of the detectives, Sergeant M. J. Wild, later told the Coroner’s Court that he saw O’Connor enter the club and sit down with three well-known underworld figures, Lenny McPherson, John Clarke and Anthony Williams. Wild said that at about 3.25 am he heard someone shout, ‘Look out, he’s got a gun,’ and then he heard a shot. Wild said that he then drew his own pistol and pushed his way through the fleeing crowd to the table where the shot had come from.

Detective Sergeant Wild said that he found O’Connor lying dead on the floor in a pool of blood which had come from a bullet wound in his head. Near O’Connor lay two pistols: a .32 calibre and a .25 calibre. Both guns had been wiped clean of fingerprints.

Detective Wild told McPherson, Clarke and Williams to put their hands on the table where they could be seen. Lenny McPherson said, ‘It’s O’Connor, Mr Wild. The bastard tried to knock us off.’ McPherson then went on to explain to the detective that O’Connor had tried to murder him because he wouldn’t help him beat the murder rap he was facing in Melbourne.

McPherson said that O’Connor had barged his way up to the table, pulled a gun from underneath his coat, aimed it at McPherson’s head and said, ‘This is for you’. With that Clarke grabbed O’Connor’s arm and pushed it away from McPherson and the gun went off and O’Connor ‘sort of’ shot himself in the head. None of the men could explain the presence of the other gun and denied having ever seen it before.

Contradicting McPherson’s story, a woman questioned by police said that she was standing near the table before the shooting and felt something drop on her foot. It was a small pistol. She said that when McPherson bent down to pick it up he apologised to her and she said to him, ‘That’s a funny thing to drop.’ McPherson did not reply.

While the police seemed to have happily arrived at the conclusion that Ducky had ‘died by his own hand’ after being thwarted in the act of murder, a Coronial Inquest decided that O’Connor was in fact either killed – as alleged by McPherson – or he was armed with one pistol and was shot by Clarke with the other.

The coroner found that the shot from the .32 pistol which killed O’Connor could have been fired either by O’Connor or another person. The coroner also commented that the lack of fingerprints on either weapon, seemingly due to some very efficient work by an unidentified person with a handkerchief, was a major factor in that no one had been charged with the killing of Ducky O’Connor.

So, whatever actually happened that night at the Latin Quarter we shall never know and what the Daily Mirror headlined as ‘the city’s fastest hankie’ soon became the joke of the underworld.

And while the coroner, the cops or the villains couldn’t agree on how Ducky became a cooked goose, they left little doubt that the general consensus of opinion was that the Sydney underworld was a much safer place without Ducky in it.