1863: The Escape-Proof Prison That Wasn’t: Captain Thunderbolt Breaks Out of Cockatoo Island

Frederick Wordsworth Ward, the bushranger known as Captain Thunderbolt, was serving time on Sydney‘s Cockatoo Island, a prison ringed by harbour currents and sheer sandstone cliffs and widely declared impossible to escape. On the night of 11 September 1863, Ward slipped his cell and plunged into the water, swimming through the cold, shark infested harbour to the mainland shore.

The breakout humiliated colonial authorities and turned Ward into a folk figure almost overnight. He spent the next seven years roaming the bush of northern New South Wales, robbing coaches, inns and travellers as one of the colony’s most enduring and elusive bushrangers before he was finally shot dead by police near Uralla in 1870.

Cockatoo Island, Sydney, 1951. Photograph by Frank Hurley. National Library of Australia, PIC FH/7951. Out of copyright.
Cockatoo Island, Sydney, 1951. Photograph by Frank Hurley. National Library of Australia, PIC FH/7951. Out of copyright.

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1876: A Cashier’s Refusal Dooms the Jesse James-Younger Gang at Northfield, Minnesota

On September 7, 1876, the Jesse James-Younger Gang rode into Northfield, Minnesota, intending to rob the First National Bank. Inside, cashier Joseph Lee Heywood refused to open the safe even as a revolver was pressed to his head and he was pistol-whipped; he was shot dead at his desk for his defiance, having falsely claimed the safe was on a time lock.

Outside, armed townspeople grabbed rifles and shotguns and opened fire from doorways and windows along the main street. Two of the raiders, Clell Miller and William Stiles, were killed in the street, and several others were wounded before the surviving gang members fled empty-handed.

A massive manhunt followed through the Minnesota countryside. Jesse and Frank James eventually broke away and escaped, but Cole, Jim and Bob Younger were tracked down two weeks later, badly wounded, and captured. The disastrous raid effectively destroyed the gang as a fighting unit and ended its run of successful robberies.

Jesse and Frank James
Jesse and Frank James

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1924: John Dillinger Commits His First Crime: A Robbery That Set a Legend in Motion

On 6 September 1924, twenty-one-year-old John Dillinger joined his friend Edgar Singleton in robbing a local grocer, Frank Morgan, as he returned home carrying the week’s takings. Dillinger struck Morgan with a cloth-wrapped iron bolt. Both men were arrested, but despite Dillinger having no prior record, he received the harsher sentence: between 10 and 20 years. Singleton, the experienced criminal who had planned the job, hired a lawyer and walked away with a lighter term.

Inside the Indiana State Reformatory, Dillinger kept his head down, worked as a seamster in the shirt factory, and carefully cultivated friendships with hardened criminals including Harry Pierpont, Homer Van Meter, and Charles Makley. These men would later form the core of the Dillinger gang. He later wrote to his father: ‘if I had gotten off more leniently when I made my first mistake this would never have happened.’

John Dillinger 1924 mugshot
John Dillinger 1924 mugshot

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1857: Two Men Hanged at Melbourne Gaol for the Brutal Murder of a Brothel Madam

On a wet, cloudy night in 1857, Chong Sigh and Hing Tzan entered the brothel of Sophia Lewis on Exhibition Street, in Melbourne, intending to rob and murder her.

Chong Sigh cut the sleeping woman’s throat, but the first wound was not fatal. Hing Tzan held her down while a second, deeper cut was made. When Lewis moved again, Hing Tzan returned to her and, according to the men’s later confession, almost severed her head from her body.

The pair then plundered the room and slipped away into the night, narrowly avoiding a constable on his beat before eventually scattering to Geelong and Ballarat.

Both men were arrested, confessed and were convicted of murder. Their statements confirmed that Chong Sigh had conceived the plot, with robbery as the motive, while Hing Tzan carried out the final fatal attack.

At Melbourne Gaol, the two men presented a striking contrast on the scaffold. Chong Sigh was overcome with emotion and cried loudly, while Hing Tzan remained comparatively composed and appeared to chant a prayer. Hing Tzan briefly resisted when the execution cap was placed over his head, apparently fearing that his hair was about to be cut, but quickly became calm. Both men were hanged on 3 September 1857.

Hooded man holding a glowing lantern in a dark forest
Hooded man holding a glowing lantern in a dark forest

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