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.


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.”


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

Published in: on April 29, 2010 at 8:37 am  Comments (47)  
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47 CommentsLeave a comment

  1. Goodness me! Look how Edward Scissorhands has changed!

    • He looks remarkably like Peter Andre 😦

      • Yeah but I’d like to see him try and use those things.

      • Its my cousin and he can use them!

  2. I’m guessing he was probably more of a gentleman then Carl Williams… oh carl would they have left milk out for you…

    • Carl was a complete tosser

  3. Sharing a time-zone with Nurse Myra, I always enjoy being among the first to dive into a freshly posted blog post and drop my humble comment in the basket of bemusement that trail after Matron Myra like helpful orderlies … 1959 must have been an exciting year in Kurri Kurri. I wonder what kind of hairstyle would make a woman go weak at the knees? Because in my case, it’s no hair at all! PS The author of Shantaram was an escapee from a jail in Melbourne.

    • I haven’t read it Mitzi – is it any good?

  4. At first glance, Dugan looks like dr.cox from scrubs

    • You’re right – he does!

  5. Simmo looks like one of the guys who use to take my lunch money away from me in junior high school.

    • I’m thinking you mean Darcy. I couldn’t find a photo of Simmo on the net which is a pity as he was rather gorgeous

  6. I’m left wondering what the lethal haircut looked like…sadly, I have yet to encounter one in my lifetime.

    • He had a “Mod” haircut

  7. I too love the idea of a lethal haircut – not just side burns then!

  8. oh, the allure of the bad boys. we say we want sensitive men, but those are the guys we drive over with our cars…

  9. Hang on, “prison tram”? You mean Sydney had a dedicated prison tram?

    Well look at its original settlers.

  10. If only he could have made it off the continent….

    Where exactly can I get a lethal haircut?

  11. What is it about Oz that pretty much every escaped convict gets such a fan base?

    • There is a tendency to support the underdog here

  12. I’m still trying to figure out what a “lethal haircut” might consist of. I’ve never really been that turned on by hair myself. It is what is under the hair and between the ears that is the real turn on, as far as I’m concerned. And I’ve also never understood the appeal of bad boys. The fact that Charles Manson has had women drooling over him, that Ted Bundy had some gal that wanted to marry him in prison has always struck me as just wrong.

    • I’m attracted to bad boys but definitely not murderers. Manson and Bundy? Those guys were seriously scary!

  13. Now, for some strange reason, I have ‘band on the run’ in my head. Odd.

    • oh gosh – what an earwig! I’m so sorry Dolce

  14. well if you’re going to be a criminal, why not a loved one? What were his crimes? Was he a bank robber or something?

    • Three charges of armed robbery, seventeen of breaking and entering, and thirty-five of car stealing.

  15. I wonder if it was the lethal haircut that killed the guard?

  16. well i always say, if you gotta get arrested, best to have a fan club! unfortunately, fans cant protect your prison wallet while in the pokey. that’s probably why he hung himself…yes his hair did look lethal.

    • Because he caused the death of a guard, he was treated with brutality by prison warders and kept in a part of the prison reserved for intractables.

      The photo is of Darcy Dugan, I couldn’t find one of Simmo, but he had a “Mod” haircut

  17. Yes what is it about bad boys….they really seem to get your blood running…straight to your loins!!!

  18. I take it Kurri Kurri is not named after the first Finnish player voted into the Hockey Hall of Fame, the great Jari Kurri. Well, damn it, it should be.

    • It’s an aboriginal word meaning “first” or “beginning”. District Surveyor T. Smith chose the name because he believed it meant ‘hurry along’ in a local dialect…..

  19. Some crims do catch the public imagination. How is Chopper Read viewed?

  20. all this talk of bad boys makes me want to recidivate.

    • You’re doing just fine the way you are P xx

  21. Why do women always go for the dangerous adventures in men? I admit, as long as it wasn’t too bad, I like a little breaking the rules. Wish I could have spent time in Sydney when I was there. Would love to see the museums.

  22. Thanks for the interesting blog. I notice one comment says they would run a mile if they saw Chopper Read. Well he lives just across the road from my shop. He comes in occasionally and wonders around, rarely buys anything. He walks a bit like a duck these days. He doesn’t have the bad boy charisma he used to have. In fact he is better known for his art works he paints and talks he gives. I think he might have or had cancer, which probably slowed him up a bit.
    Cheers Mark

    • Yeah, I’ve seen some of his artwork. It’s not to my taste.

  23. So that is how I become every teenage girls fantasy as opposed to every mentally ill womans or welfare moms like I am now?

  24. I loved being able to put these names to a place, so to speak…Keepin it nice and local Nurse Myra. Even Kurri Kurri is on my radar as my brother once lived there. I enjoyed this little taste of Sydney’s underworld, with thanks….

  25. Kevin John Simmonds, the bad-boy romantic hero, Australia’s mid 20th century handsome anti-authoritarian idol in the Ned Kelly mould …. such a sad ending for such an adventurous young man. Why do we not hear more about him?

    • you will one day.

  26. “Don’t make him a hero” was the white headline on black background in the Melbourne daily newspaper in 1959. Below the bold type headline and beside a photograph of an extraordinarily handsome, fresh-faced, healthy, 23 year old Kevin John Simmonds the article began: “The State Government Psychiatrist, Dr John McGeorge, today expressed concern at the growing admiration among teenagers for Kevin John Simmonds. He warned parents there was a serious danger that Simmonds might become a hero to children and unthinking sections of the public.” Well, here I am now, fifty-five years later, law-abiding, tertiary educated, still thinking, nearing 70, no longer a schoolboy, and still the State Government Psychiatrist’s warning has not removed Kevin John Simmonds from my short list of adventurous heroes.

  27. I am a good friend of Newcombe and he has gone straight ever since being released and holds a pretty impressive work portfolio including senior management positions,I have told him many times he should never have committed that terrible crime,he says that they wanted the easy life,women,drinking,gambling and the best although Simmonds was not a drinker I believe,thay sured have been tried for murder,and I have told him this.

  28. Newcombe passed away Oct 2014.he did tell me a few untruths that I found out after he passed away,but he had that personality that made you think butter wouldn’t melt in his mouth.

    • please get in contact with me.

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