Photo of Tara Oldfield

Author: Tara Oldfield

Senior Communications Advisor

It took Wentworth Miller and the gang an entire season of television to break out of Fox River Prison. Clint Eastwood and his buddies spent months digging through the walls of Alcatraz. And the Shawshank escape took years! This real-life escape from Pentridge didn’t take nearly as long, nor as much planning, as any of these fictional tales.

According to the newspapers following the 1955 escape of five prisoners, one of the escapees had earlier warned:

“I’ll be out in two weeks and as free as you.”

The 27th day of August, 1955

It was a sunny Saturday afternoon at Pentridge and 76 prisoners were taking part playing and watching a game of football in the farm area of the gaol - a regular occurrence for B and C Division prisoners. Included on the ground that day:

  • Peter Leslie Dawson, a thief serving five and a half years

  • Kevin Arnold McGarry, serving nine years for two charges of robbery under arms

  • William O’Meally, a convicted murderer imprisoned for life

  • Raymond Kevin Morrison, serving fifteen months for illegal use of motor cars

  • John Henry Taylor, serving a ten year sentence for three charges of robbery under arms.

The football game was being supervised by three unarmed gaol warders who proved no match for the above assailants when, at the conclusion of the match, they made their escape. 

front gates of prison
Pentridge Gaol, circa 1940s/50s VPRS 10516 P3 Unit 20.


Not just a lucky escape

The farm area where football games were played at Pentridge was unguarded at night. In the Board of Inquiry report in our collection, it’s deduced that guns were earlier brought in by outsiders under the cloak of darkness. The guns then lay waiting in the bushes for the Saturday match for prisoners Dawson and Taylor to retrieve them. The report states:

“At the conclusion of the match, at 3.15pm, the three warders in attendance, who were unarmed, were suddenly confronted and menaced, at a range of about 9 feet, by the prisoners Dawson and Taylor, who were then armed with a rifle and shot-gun, respectively. The three other escapees joined in, and two of the warders, named Elliott and Walton, were seized by the arms, and hurried, with threats, to an unoccupied control tower, known as No. 13 Post, on the outer wall, about 170 yards away. There the five prisoners climbed up a rope affixed to the wall, which controls the ladder to the post, and dropped to the other side, taking the firearms with them, and leaving the two warders inside. While all this was taking place, shots were fired from the three nearest occupied posts, but without apparent effect. The third warder, Mr Scoberg, who had been left with the other 71 prisoners, after sounding the alarm on his whistle, returned them to the gaol without further trouble.”

It is a wonder more prisoners didn’t seize the opportunity to make their own escape, riding the coat tails of the five who planned it.

Outside the prison walls

The jail-breakers weren’t on foot for very long. Detailed in the inquiry report, two men were sitting in their car on Drummond Street in Coburg when they were confronted by one of the escapees and ordered out of the car at gunpoint. While the escapee rested the gun on his lap and looked back towards the gaol, one of the civilian men seized the gun and threatened the escapee with it. The escapee put foot to pedal and drove the car towards Bell Street. The car stopped briefly to pick up another escapee while the civilian man shot at it to no avail. The civilian men were then confronted by two more escapees who promptly took back the gun and followed after the car! It was those second two escapees that forced a married couple and the wife’s brother out of their car. The two escapees, like the first two, got clean away.   


McGarry, O’Meally and Morrison were quickly recaptured but Dawson and Taylor proved more difficult for police.

“Victoria’s 3,000 police have turned the State into a vast mantrap in their search for two of five convicts who escaped from Pentridge Gaol on Saturday.”

The Argus, 29 Aug 1955, courtesy NLA Trove.


Unbeknownst to the police at the time, Dawson and Taylor had been taken in by a woman named Lillian Jean Boundy. The papers described her as the “broken hearted” lover of a man still serving time at Pentridge. She fed the men, bathed a bullet wound Dawson had acquired during the escape, and assisted them in checking into hotels. Her hospitality didn’t save the men from recapture however. The lure of a Collingwood jeweller proved armed robber Taylor’s undoing. Journalist George Gaertner reported how he’d seen Taylor after the robbery, crash the black Holden he was driving into a Chevrolet before being recaptured by police who’d been chasing them. Though Dawson had held up the store with Taylor, he couldn’t be found by police at first, as they searched the area extensively.

photo of man's face
The Argus, 7 Sept 1955, courtesy NLA Trove.


But by the next day police had also recaptured Dawson who’d been seeking refuge at a house in North Richmond. The men who’d been harbouring him were also arrested.

The inquiry

The resulting inquiry found many failures on the part of Pentridge management contributed to the escape, including:

  • inadequate security surrounding the football ground

  • security risk of individual prisoners not taken into account when selecting players for the football teams

  • the fact that the warders were unarmed

  • inadequate gun training for armed guards in the control towers

  • lack of a search for contraband hidden around the football ground prior to playing the match.

“That an escape such as this from Pentridge, which is properly regarded as the State’s ‘maximum security’ prison, should have been possible must of necessity cause uneasiness in the public mind, particularly when, as was the case, there had been three other successful escapes from the same prison within the preceding ten months… it must be agreed that the evidence given at this inquiry disclosed a lack of precautions which, to the criminal mind, made this escape quite an easy matter. I find that the principal responsibility for the lack of precautions lies with the Governor.”

Recommendations were made to address the failings including that the outer wall of the farm area be made more secure, that sporting activities be confined to the Gaol proper, and that more effective rifles and better training be applied, to name a few. 

front page of a report
Report of the Board of Inquiry, front cover, VPRS 2965 P0 Unit 1.


Other criminals weighed in on the findings in the media, declaring:

“Pentridge is the easiest gaol I have had to escape from. All you need is plenty of ‘guts’ and the ability to keep running,” Maxwell Carl Skinner.

Pentridge records

Find the report via this link.

You can search records of the agency His Majesty's Gaol, Pentridge (known as Pentridge Prison) here. Records include returns of executed criminals, prison governor’s journals and even a register of prisoner correspondence just to name a few. 


Listen to the PROV podcast Look history in the eye episode Pentridge Prison Escape.

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