Al Capone All-American: Cicero & Politics

Al Capone All-American: Cicero & Politics

From The Outfit by Headgum

February 5, 2026 · 59 min

About this episode

The episode discusses the political unrest in 1923 Chicago and the rise of a mayoral candidate against bootleggers, focusing on Al Capone's operations in Cicero.

As a wave of political unrest sweeps 1923 Chicago, along comes the rise of a progressive mayoral candidate who vows to take down the bootleggers, effectively driving Al Capone’s operation to the suburb of Cicero, Illinois. In this week’s installment of “Al Capone All-American,” Dan and Alana find the Outfit’s bloody assault on democracy in Cicero is but a prelude for their return to Chicago—installing a buffoonish new mayor all-too reminiscent of a current-day executive. Sources Historian Mario Gomes's excellent website, My Al Capone Museum ( https://www.myalcaponemuseum.com/ ) Capone: The Man and the Era  by Laurence Bergreen Mr. Capone: The Real - and Complete - Story of Al Capone , by Robert J. Schoenberg Capone: The Life and World of Al Capone  by John Kobler Al Capone: His Life, Legacy, and Legend  by Deirdre Bair The Wicked City: Chicago From Kenna to Capone  by Curt Johnson with R. Craig Sautter Al Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition  by John Binder Gangland Chicago: Criminality and Lawlessness in the Windy City  by Richard C. Lindberg Prohibition Gangsters: The Rise and Fall of a Bad…

People in this episode

Hosts: Dan, Alana

Topics covered

  • Al Capone
  • Chicago history
  • Prohibition
  • political unrest
  • organized crime
  • Cicero

Keywords

  • Al Capone
  • Cicero
  • Prohibition
  • bootleggers
  • Chicago history
  • politics
  • organized crime

Mentioned in this episode

Organizations: The Chicago Historical Homicide Project, The Chicago Defender

Books & works: Capone: The Man and the Era, Mr. Capone: The Real - and Complete - Story of Al Capone, Capone: The Life and World of Al Capone, Al Capone: His Life, Legacy, and Legend, The Wicked City: Chicago From Kenna to Capone, Al Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition, Gangland Chicago: Criminality and Lawlessness in the Windy City, Prohibition Gangsters: The Rise and Fall of a Bad Generation, The Outfit: The Role of Chicago's Underworld in the Shaping of Modern America, The Mostly True Story of America’s First Black Private Investigator

Places: Cicero, Illinois, Chicago

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