Prison - Dark Stories True Crime Tours

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.’

⬅ See all events from 6 September

Gang Organised Crime Prison Robbery USA

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1991: Pee Wee Gaskins Executed for a Murder Committed Behind Bars

Donald Henry Gaskins Jr., known as Pee Wee Gaskins, was executed in the electric chair at Broad River Correctional Institution in South Carolina at 1:10 a.m. on 6 September 1991, aged 58. A serial killer confirmed to have murdered at least thirteen people between 1970 and 1975, including six teenagers and a two-year-old, he had originally been sentenced to death in 1976 for one of eight bodies found buried near his home in Prospect, South Carolina. That sentence was overturned, and he pleaded guilty to nine murders in exchange for life imprisonment.

His second death sentence came after he murdered a fellow death row inmate, Rudolph Tyner, using C4 explosive while incarcerated at Central Correctional Institution in Columbia. Hours before his execution, Gaskins attempted suicide by slitting his wrists. He claimed to have killed 110 people, a figure widely dismissed by law enforcement and journalists as a bid for notoriety.

His last words were: ‘I’ll let my lawyers talk for me. I’m ready to go.’

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Execution Murder Prison Serial Killer USA

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1946: The Lipstick Killer Pleads Guilty, Then Tries to Cheat the Verdict

On September 4, 1946, William Heirens stood before a Chicago court with his parents and the victims’ families watching, and admitted guilt on burglary and murder charges spanning three killings. The prosecution had already staged a public reenactment of the Degnan murder in August, ensuring the case was tried in the press long before sentencing.

That night, Heirens attempted to hang himself in his cell, timing the attempt to coincide with a guard shift change. He was discovered before he died. He later said: ‘Everyone believed I was guilty … If I weren’t alive, I felt I could avoid being adjudged guilty by the law and thereby gain some victory. Before I walked into the courtroom my counsel told me to just enter a plea of guilty and keep my mouth shut afterward. I didn’t even have a trial.’

Red lipstick with blood splatter on white background, close up

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Murder Prison Serial Killer Trial USA

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1809: Thomas Dowlan Hanged in Sydney for Burglary at Hawkesbury

Thomas Doolan, described as an old offender who had been tried several times in the colony, was convicted of forcibly breaking into the house of John Styles at Hawkesbury. He had previously saved himself from execution by turning informant against his accomplices, some of whom were hanged on his testimony.

Doolan was hanged in Sydney on 26 August 1809. Court records from the same period reveal he had also been among those who burglariously broke into the dwelling of a settler named Thomas Harley, beating the occupants and ransacking the house, though he did not live to face that additional charge.

Motorway 1 bridge over Hawkesbury River near Sydney with traffic

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Australia Burglary Execution Hawkesbury NSW Prison Robbery Sydney

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