Organised Crime - Dark Stories True Crime Tours

1919: Congress Overrides a Veto and Unleashes Prohibition: the Volstead Act Becomes Law

President Woodrow Wilson vetoed it, warning that banning alcohol while rationing wartime grain made no sense now the war was over. Congress disagreed, and on this day in 1919 the Senate and House of Representatives overrode his veto, pushing the Volstead Act into law and setting a date to enforce the newly ratified Eighteenth Amendment.

The Act gave Prohibition its teeth: it defined any drink over 0.5 percent alcohol as illegal and handed federal agents the power to raid, seize and prosecute. Within months, that vacuum would be filled not by sobriety but by bootleggers, speakeasies and the organised crime syndicates who built fortunes smuggling what the law had just made forbidden.

New York City Deputy Police Commissioner overseeing the disposal of confiscated liquor during Prohibition, c. 1921. Source: Library of Congress.

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1927: Laid Up with Influenza, Snowy Cutmore Was Shot Dead in His Sickbed by Squizzy Taylor

Snowy Cutmore had spent months hiding in Sydney after the gangland killing of an ally, but by late October 1927 he was back in Melbourne, lodging with his mother in Carlton. At the races he ran into his old rival Squizzy Taylor and the two traded threats in public; within days Cutmore came down with influenza and took to his sickbed.

On 27 October 1927, Taylor and an accomplice hired a car, drove to the house and walked straight into Cutmore's bedroom. Gunfire erupted between the bedridden man and his visitors: Cutmore was hit five times, his mother was wounded by a stray bullet as she rushed in, and Taylor himself staggered out mortally wounded, dying in hospital within the hour.

Snowy Cutmore dual portrait image from 1920

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1927: The Last Gamble of Squizzy Taylor: a Bedroom Shootout in Melbourne

Squizzy Taylor, Melbourne's most infamous gang leader, walked into a Carlton sickroom on 27 October 1927 to settle an old score with his bedridden rival, John "Snowy" Cutmore. Within minutes, gunfire tore through the small house and both men were mortally wounded.

Taylor was rushed to St Vincent's Hospital in nearby Fitzroy, where he died that evening, aged 39, without ever naming who had fired the fatal shot.

The inquest returned an open verdict. One enduring theory holds that it was not Cutmore but his mother, standing over her dying son, who pulled the trigger that finally brought down Melbourne's most feared gangster.

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1957: The Lord High Executioner of Murder Inc Gunned Down in a Barbers Chair

Albert Anastasia had spent two decades building a reputation as the most feared man in organised crime, running Murder, Inc., the Mafia's contract-killing squad blamed for thousands of unsolved deaths, which earned him the nickname the Lord High Executioner. By the mid-1950s he had clawed his way to boss of his own crime family, but his brutal, unpredictable style had made him more enemies than allies.

On 25 October 1957, Anastasia settled into the barber's chair at a Manhattan hotel for a shave. His driver had parked the car and stepped outside, leaving him unguarded. Two gunmen with scarves hiding their faces burst in, shoved the barber aside and opened fire, chasing Anastasia as he staggered into the mirror before he fell dead. No one was ever charged, though a rival mobster later boasted to an associate, "You can just call the five of us the barbershop quintet."

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