History Daily: The St. Valentine’s Day Massacre

Release Date: February 14, 2025
Host: Lindsey Graham
Produced by Airship, Noiser, and Wondery

Introduction: Setting the Scene (00:00 - 05:32)

On a frigid morning of February 14, 1929, Chicago becomes the backdrop for one of the most infamous events in American organized crime history—the St. Valentine’s Day Massacre. Host Lindsey Graham transports listeners to a dimly lit garage on Chicago’s north side where six members of the Northside Gang, dressed in pinstripe suits and fedoras, await a delayed shipment of bootlegged whiskey. The tension is palpable as Frank Gusenberg, a young mobster, grows impatient with the shipment's lateness.

Graham explains, “[Prohibition] made it illegal to sell, manufacture, or transport booze, but it said nothing about drinking it” (00:46). This loophole ignited a massive demand for illegal alcohol, fueling the rise of organized crime and sparking fierce rivalries, particularly between the Northside Gang and the Chicago Outfit led by Al Capone.

The Rivalry Escalates: From Prohibition to Power (05:32 - 17:49)

Delving into the origins of this rivalry, Graham narrates the rise of Al Capone under the mentorship of Johnny Torrio, the boss of the Chicago Outfit. Initially a lowly bouncer, Capone’s acumen in bootlegging operations propels him to prominence. The enforcement of the Volstead Act in January 1920 catalyzes the burgeoning black market for alcohol, with the Chicago Outfit swiftly capitalizing on the opportunity.

However, competition is fierce. The Northside Gang, led by Dion O'Banion, challenges Capone’s dominance. In 1924, a failed negotiation over territorial agreements leads to O'Banion’s brutal assassination on November 11, 1924. This act plunges Chicago into the chaotic Beer Wars, marked by relentless violence as gangs vie for supremacy.

Graham recounts a pivotal moment on January 24, 1925, when Johnny Torrio survives a near-fatal shotgun attack orchestrated by Bugs Moran and Jaime Weiss of the Northside Gang. This event forces Torrio to retire, passing the baton to Capone, who then solidifies his control over Chicago's bootlegging empire, boasting an annual income exceeding $100 million by 1926.

The Massacre Unfolds: February 14, 1929 (13:00 - 19:17)

On Valentine’s Day, the simmering tensions reach a boiling point. As the Northside Gang members gather in a garage to secure the awaited whiskey shipment, four men masquerading as police officers enter the scene. Graham describes the chilling sequence: “Bullets tear through fabric and flesh and ricochet off the brick walls” (10:50), leading to the deaths of seven men, including Frank and Peter Gusenberg.

Detective Sergeant Thomas J. Loftus arrives at the crime scene, identifying the victims and grappling with the brutality of the massacre. Despite initial suspicions pointing towards Capone, his alibi places him vacationing in Miami Beach at the time of the shooting. Investigators explore theories of corrupt police officers being involved, citing inconsistent witness reports of officers seen fleeing in a black Cadillac.

The Aftermath and Investigation (19:17 - 23:10)

The massacre ignites a national outrage, pressuring the federal government to address the rampant organized crime spurred by Prohibition. U.S. Attorney George E. Q. Johnson spearheads the investigation, yet lack of concrete evidence hampers efforts to directly implicate Capone.

As President Herbert Hoover takes office in March 1929, he establishes a federal task force focused on Al Capone, not through traditional law enforcement channels but via the Treasury Department. Concurrently, Agent Elliot Ness and his team, famously known as "The Untouchables," intensify their pursuit by targeting Capone’s financial malpractices.

Graham highlights a critical turning point: “If they can't arrest Capone for orchestrating the massacre, maybe they can get him for cheating on his taxes” (11:40). This strategic shift leads to Capone’s eventual downfall in 1931, when he is convicted on tax evasion charges and sentenced to 11 years in Alcatraz.

Long-term Consequences: The End of Prohibition (23:10 - Episode Conclusion)

The St. Valentine’s Day Massacre not only marks the decline of Capone’s empire but also serves as a catalyst for the repeal of Prohibition. President Hoover, despite the Wickersham Committee’s findings that Prohibition was ineffective and fueled organized crime, remains steadfast in his support. However, public opinion shifts dramatically amidst the Great Depression, and Franklin D. Roosevelt’s victory in the 1932 election underscores the nation’s desire for change.

In February 1933, the 21st Amendment is ratified, officially repealing the 18th Amendment and ending the Prohibition era. Graham concludes, “After 13 long years, the age of gangsters, speakeasies, and bootlegging comes to an end, in part as a result of the gangland violence that occurred in a cold Chicago garage on February 14, 1929” (19:17).

Key Quotes

• Lindsey Graham (00:46): “Prohibition made it illegal to sell, manufacture, or transport booze, but it said nothing about drinking it.”

• Lindsey Graham (10:50): “Bullets tear through fabric and flesh and ricochet off the brick walls.”

• Lindsey Graham (11:40): “If they can't arrest Capone for orchestrating the massacre, maybe they can get him for cheating on his taxes.”

Conclusion

The St. Valentine’s Day Massacre stands as a pivotal moment in American history, illustrating the profound impact of Prohibition on societal dynamics and the rise and fall of notorious gangsters like Al Capone. Through meticulous research and engaging narration, Lindsey Graham provides a comprehensive exploration of how a single night of violence precipitated significant legal and cultural transformations in the United States.

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Produced by:

• Host: Lindsey Graham
• Audio Editing: Molly Bach
• Sound Design: Misha Stanton
• Music: Lindsey Graham
• Research: Joe Viner
• Executive Producers: Steven Walters (Airship) and Pascal Hughes (Nooser)

Available on Wondery and other major podcast platforms.