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Five Ways to Escape Cockatoo Island (if you’re a convict) (blog)

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Due to its location on Sydney Harbour, Cockatoo Island was an ideal place to imprison criminals during Australia’s colonial era. Indeed, from 1839 to 1869, the island operated as a convict penal establishment, where repeat male offenders undertook hard labour.

Although the surrounding waters were deep and shark-infested, and convicts were known to have worn leg-irons, that didn’t stop several from seeking to defy the odds and escape… of course, only a select few managed pulled off the near impossible. Read on to discover five of the most remarkable escape attempts.

1. The human jellyfish

A Sydneysider by the name of Michael Smith, aka ‘Long Mick’, claimed to have escaped Cockatoo Island during the 1840s, putting an unlawful end to what was meant to be a long prison sentence. For many years, he boasted of this incredible feat to fellow patrons of his local pub in Lane Cove.

According to Long Mick, he escaped under the cover of darkness and – by swimming in a plodding, jellyfish-like manner– managed to stay afloat in his leg-irons and reach Greenwich Point after several gruelling hours. He admitted he might have failed at the finish line if it weren’t for a chance encounter with a sympathetic former convict who helped him remove his leg-irons after he crawled ashore. While many vouched for Long Mick, no one knows for sure if his daring escape is fact or fiction.

2. The master of disguise

David Clarke, aka Josiah Goodgame, was – according to the Sydney Morning Herald (12 July 1860) – a ‘determined and daring villain’ with a knack for escaping custody. By the time he arrived at Cockatoo Island in 1859 to serve out a life sentence, he had already escaped Port Arthur Penitentiary in Tasmania and Pentridge Gaol in Victoria.

The following year, Clarke cemented his reputation as a serial escapist with an audacious breakout attempt. Donning a disguise, he slipped out of a busy convict workshop and hid from the island’s guards amongst the island’s rocks. He endured hunger, thirst and the freezing cold for four days and three nights before the authorities abandoned their search for him.

A few days later, sentries spotted him fleeing the island with a makeshift float, held together with rope, and threatened to shoot if he didn’t surrender. Clarke pleaded for mercy, claiming he was already on the verge of death. Although he was placed back in custody, in many ways he did succeed in escaping Cockatoo Island – due to the physical toll of his efforts, he was transferred from the island to a hospital to recuperate.

3. The breakout boy

Like Clarke, John Crudden was known for his relentless pursuit of freedom. When the Irish national arrived in the colony in early 1840 to serve a gaol sentence for stealing, he was only 11 years old.

Crudden was initially placed in the care of a pastoralist but was transferred to Hyde Park Barracks after his guardian flogged him for losing pigs. During his time at Hyde Park Barracks, he hid to avoid work and escaped custody a total of three times. Consequently, he received several floggings and, eventually, was sent to Cockatoo Island in March 1842. Although Crudden was now 14 years of age, he was only four feet four inches tall and, thus, still too small for the prison shirts.

In November, that same year, Crudden escaped from the island by swimming to the shore. He was tracked down, however, and returned to the Island. For his actions, Crudden was placed in irons for twelve months and made to work at the quarry.

This was not the only punishment Crudden was subject to while incarcerated at Cockatoo Island. Records reveal that by 1849, he had endured 2 years in irons, 109 days in lockup and at least 202 lashes. He received the bulk of these lashes when he was 15, making him the youngets person to be flogged on the island.

Not to be deterred by the discipline that had been doled out, Crudden made further escape attempts. Notably, in September 1853, he secured help from a sympathetic boatman and departed the island, hidden in the stern of a vessel. When a fellow prisoner informed on him, Crudden was recaptured and placed in solitary confinement.

4. The toilet tunnelers

In July 1860, 2 prisoners attempted to escape the island by dislodging stone flagging from the ground and undermining prison walls so they could descend into a large sewer drain beneath a privy. The men were hoping to follow the drain to the harbour but, unfortunately, they became stuck and had to be rescued.

After the guards tried unsuccessfully to flush the men out with water, a fellow convict who served as a wardsman descended into the sewer to dislodge them. The prisoners were recaptured and punished, and the wardsman, having helped in their capture, was beaten by his peers.

5. The legendary bushranger

Cockatoo Island’s most infamous convict is arguably Frederick Ward. On 11 September 1863, Ward cemented his place in Australian folklore when he escaped Cockatoo Island with fellow convict, Fred Britten. According to one legend, Ward’s wife – Worimi woman Mary Ann Bugg – was instrumental in this feat.

Namely, she swam to the island from Balmain and left a file for Ward and Britten to remove their chains. After a swim through shark-infested waters, Ward made it to shore where Bugg was waiting with a horse and they rode to freedom. Ward subsequently gained notoriety as the outlaw Captain Thunderbolt and embarked on a bushranging spree that culminated in his death in 1870.

Want to learn more about the turbulent history of Cockatoo Island’s former penal establishment and visit the Convict Precinct in person? Book tickets to our guided Convict Precinct Tour.


Helpful links

Looking to learn more about Cockatoo Island? Here are some useful links.