After Dark: Myths, Misdeeds & the Paranormal

Al Capone and the Valentine's Day Massacre

Feb 5, 2026
Jonathan Eig, Pulitzer-winning biographer and historian of Al Capone, brings Prohibition-era grit. He traces how bootlegging, corrupt police and rival gangs set the stage. He recreates the massacre night, the shocking press coverage, theories about cops in uniforms, and how investigators ultimately built a tax case that toppled Capone.
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INSIGHT

State-Made Black Market Fueled Crime

  • Prohibition created a huge, state-made black market that criminal groups quickly dominated.
  • The law's lack of enforcement turned bootlegging into enormous, violent profit wars.
INSIGHT

Corruption Made Policing Ineffective

  • Police were poorly paid and easily bribed, making law enforcement ineffective against gangs.
  • Corruption meant dozens of murders produced almost no convictions during Prohibition-era Chicago.
ANECDOTE

The Clark Street Garage Execution

  • On February 14, 1929, seven men waited in a Clark Street garage and were executed inside after men in police uniforms entered.
  • One survivor briefly told investigators "the cops did it" before dying, leaving the crime shrouded in mystery.
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