Stuff You Should Know

SYSK’s Fall True Crime Playlist: How The Great Train Robbery Worked

September 26, 2025

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  • The Great Train Robbery of 1963 involved 15 men, including members of the Bowler Hat Gang and the South Coast Raiders, who successfully robbed the UP Special mail train of approximately 2.6 million pounds, an amount worth over $100 million today. 
  • The severity of the robbers' sentences, often 30 years, was unusually harsh for a robbery where no one was killed, especially compared to a judge's prior leniency in a case involving a fatality. 
  • A major factor in the public's perception of the robbers as folk heroes was undermined by the violent assault on the train conductor, Jack Mills, which shifted sentiment against the gang. 

Segments

Introduction to the Heist
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(00:00:54)
  • Key Takeaway: The Great Train Robbery involved 15 men robbing a British mail train in 1963 without using guns, and most of the money was never recovered.
  • Summary: The episode introduces the 1963 Great Train Robbery, a daring heist carried out by 15 men in the UK against a British mail train. The robbers managed the crime without firearms, though most were eventually caught. A significant portion of the stolen money remains missing.
Gang Formation and Target Selection
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(00:06:08)
  • Key Takeaway: The robbery was planned by merging the Bowler Hat Gang and the South Coast Raiders, targeting the UP Special train due to its minimal security.
  • Summary: The initial idea came from a man named Fields, leading to a partnership between the Bowler Hat Gang (led by Bruce Reynolds) and the South Coast Raiders (led by Buster Edwards). They specifically targeted the UP Special, a mail sorting train running between Glasgow and London, because it carried large sums of cash with little armed security.
Inside Man and Bank Holiday Timing
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(00:09:32)
  • Key Takeaway: The identity of the inside informant, codenamed ‘Ulster Man,’ was recently revealed as Patrick McKenna, who advised the gang to strike after a bank holiday for a larger take.
  • Summary: The gang relied on an inside man, ‘Ulster Man,’ whose identity was recently revealed as Patrick McKenna. McKenna recommended robbing the train on the day after a bank holiday, resulting in the train carrying about 2.6 million pounds, significantly more than the usual 300,000 pounds.
The Robbery Execution Details
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(00:14:31)
  • Key Takeaway: The plan involved awkwardly rigging the railway signals and violently assaulting the conductor, Jack Mills, with an iron ‘cosh’ to move the train to the drop point.
  • Summary: The gang stopped the train by awkwardly wiring the signal light to show red, then boarded and assaulted the conductor, Jack Mills, with an iron ‘cosh’ (billy club/crowbar). They failed to use their recruited driver, forcing the injured Mills to drive the train another mile and a half to the designated drop point, Bridigo Bridge.
Hiding Out and Initial Capture
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(00:22:40)
  • Key Takeaway: The gang’s plan to hide for 30 minutes at Leather Slade Farm was undone when police learned of the delay, leading neighbors to report the unusual gathering of 15 men.
  • Summary: The robbers moved the loot using a lorry and Land Rovers to a prearranged hideout, Leather Slade Farm, intending to lay low for eight days. However, the police announcement that the robbers were likely within a 30-mile radius alerted locals, and a neighbor reported the large number of men at the farm, leading to the initial arrests.
Trial, Sentences, and Acquittals
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(00:28:06)
  • Key Takeaway: Most robbers received unusually harsh 30-year sentences, but one man was acquitted due to defense successfully arguing his fingerprints on a Monopoly board were not conclusive evidence.
  • Summary: The trial began in January, with Ronnie Biggs separated due to his prior record. While most received 30-year sentences, one man was acquitted because his prints on a Monopoly game could not be definitively linked to the crime. There are claims that police planted evidence, such as yellow paint on a shoe, against some defendants.
The Fate of the Robbers
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(00:37:07)
  • Key Takeaway: Several robbers escaped prison, most famously Ronnie Biggs, who evaded capture for decades, partly due to Brazilian extradition laws protecting parents of citizens.
  • Summary: After sentencing, several robbers escaped, including Charlie Wilson and Ronnie Biggs, who fled to Australia and then Brazil. Biggs lived openly in Brazil for years, protected from extradition because he was the parent of a Brazilian citizen. While many robbers met tragic ends, others simply retired, and most did not become wealthy from the heist.
Listener Mail: Horse Milk
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(00:45:09)
  • Key Takeaway: Kumis, a mildly alcoholic fermented drink from Kazakhstan made from horse milk, is described as having a sour, vodka-like bite combined with the ‘disgusting tang’ of horse milk.
  • Summary: Listeners shared experiences with Kumis, a traditional drink from Kazakhstan made from fermented horse milk. Due to higher natural sugars, Kumis becomes mildly alcoholic. One listener described it as a combination of sour yogurt, vodka bite, and the unique flavor of horse milk, noting that pickled rooster comb was even more disagreeable.