Simmo on the run

Back in 1959, one man had the attention of most Australians.

A marathon manhunt was underway for daring Long Bay Gaol escapees Kevin John Simmonds and Leslie Alan Newcombe. Newcombe was soon recaptured, but Simmonds, aged 24, remained on the run for five weeks before being found near Kurri Kurri.

Kurri Kurri

By that time, the grimy, shoeless, starving and exhausted young criminal had achieved folk hero status as a will o’ the wisp, eluding the most costly pursuit in the state’s history by hiding out in swamps and leech and tick-infested country.

Simmo had a penchant for fast cars and a reputation as a sharp dresser, crocodile skin shoes and black satin shirts were a big part of his pre prison wardrobe, plus he had a ‘lethal haircut’,  guaranteed to make women weak at the knees.

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He and Newcombe escaped through a chapel ventilator shaft, scaled a wall and hot wired a car parked outside Prince Henry Hospital. They spent their first free night crouched in a freshly dug grave at Botany Cemetery then hid for a week in the pig pavilion at the Sydney Showground.

Cemetery at Prince Henry Hospital

An anti-establishment group known as the Libertarians printed a poster of the odds facing Simmonds “One man versus 500 fearless coppers and 300 righteous civilians armed with submachine guns, pistols and teargas.”

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Schoolgirls confessed he had replaced Elvis as the subject of their teenage dreams, housewives left bottles of milk on their doorsteps after it was reported to be his favourite drink. Sydney eccentric Bea Miles claimed to be arranging a passport for him.

Bea Miles

When he was finally captured, fans bearing gifts and chocolates mobbed the courthouse at Wyong chanting “We Want Kevin”. The judge was unimpressed and convicted him of the manslaughter of a prison guard who had been killed during the escape. Thousands of cards and letters were sent to his parents after his sentencing, several of these included offers of marriage.

Sadly, Simmo did not fare well in prison and hung himself in 1966. His sister Jan wrote a book about him and 14 years later, in a strange coincidence, married Darcy Ezekiel Dugan, Sydney’s most notorious prison escape artist who spent more than 40 years behind bars.

On 4 March 1946, Darcy Dugan escaped from a prison tram which was transporting him between Darlinghurst Courthouse and Long Bay Gaol. As the tram passed the Sydney Cricket Ground, Dugan used a kitchen knife to saw a hole through the roof, through which he escaped. The tram is still kept today at the Sydney Tramway Museum.

Darcy Dugan