After Dark: Myths, Misdeeds & the Paranormal

Episode Summary: Al Capone and the Valentine's Day Massacre

Release Date: February 5, 2026
Host(s): Anthony Delaney, Maddie Pelling
Guest: Jonathan Eig (Pulitzer Prize-winning author of "Get Capone: The Secret Plot That Captured America's Most Wanted Gangster")

Overview

This episode delves into one of the darkest and most notorious events of Prohibition-era America: the St. Valentine’s Day Massacre. Hosts Anthony and Maddie, joined by eminent historian Jonathan Eig, dissect the conditions that birthed gangland Chicago, the personalities at its heart—most notably Al Capone—and the enduring mythos and consequences of the massacre. They explore how the event became national news, the ambiguity that still surrounds its perpetrators, and its pivotal role in shaping policy and popular culture in the years that followed.

Key Discussion Points & Insights

1. Setting the Scene: Prohibition and Chicago’s Criminal Underworld

[01:22–05:45]

• Prohibition’s Unintended Consequences:
  • The 1920 ban on the sale and distribution of alcohol in the U.S. quickly led to a lucrative black market, as people refused to give up drinking.
  • "Almost immediately, the rule was flouted. People did not want to give up their booze... the government never had a plan for enforcing Prohibition." – Jonathan Eig [05:45]
• Rise of Organised Crime:
  • Criminals saw opportunity, shifting from existing vice trades to bootlegging.
  • Fierce competition and huge profits led to violent clashes among rival gangs.

2. Chicago’s Gangs & Their Leaders

[08:06–14:55]

• Al Capone and His Rivals:
  • Capone—celebrity, feared leader—embodied Prohibition-era gangsterism.
  • Notable rivals included George "Bugs" Moran of the Northside Gang and "Machine Gun" McGurn.
• Ethnic Dynamics:
  • Gangs often aligned along ethnic lines (Irish, Italian, Jewish), mirroring Chicago’s immigrant makeup.
  • "There is a lot of ethnic influence... Capone's gang was actually fairly non-denominational." – Jonathan Eig [14:55]
• Media’s Role in Myth-Making:
  • Nicknames like "Scarface" and "Machine Gun" amplified the drama, often crafted by and for the press.
  • The violence and spectacle became both local entertainment and a tourist draw.

3. Corruption and Law Enforcement

[10:00–11:42; 23:21–24:24]

• Symbiotic Relationship:
  • Gangsters routinely bribed police, prosecutors, and judges; underfunded law enforcement proved easy to corrupt.
  • "The cops were in Capone's pocket... the only real concern was your rivals." – Jonathan Eig [10:24]
• Blurring Lines:
  • Gangs often operated with impunity, aided by compromised officials and, possibly, by the active involvement of police in key crimes.

4. The Massacre: What Happened on February 14, 1929?

[17:44–22:31]

• The Lure and The Setup:
  • Capone's men allegedly set up a fake whiskey delivery to draw rival Northsiders to a garage.
  • Precise details and ultimate mastermind remain unclear to this day.
• The Execution:
  • “Seven men were in that garage early on Valentine's Day morning waiting for somebody.” – Jonathan Eig [18:10]
  • Killers, some dressed as police, lined up the men and executed them with machine guns.
• Eyewitness Testimony:
  • One severely wounded survivor told investigating officers: “This was the cops who did it. I'm not going to talk to you.” [19:27]

5. The Impact and Fallout

[22:31–28:59]

• Lasting Shock and Media Sensation:
  • Grisly photos published in tabloids shocked Americans; the event’s visibility set it apart from other gangland killings.
  • "Part of it is because of the media... Americans are waking up to pictures of the Valentine's Day massacre the likes of which they have never before seen." – Jonathan Eig [21:06]
• Public Outcry and Political Ramifications:
  • National outrage fueled by media coverage led to calls for a crackdown on organized crime.
  • President Herbert Hoover became obsessed with “getting Capone” for symbolic reasons, regardless of direct evidence tying him to the massacre.

6. Gun Culture and Policing

[28:59–29:34]

• Rise of Machine Guns:
  • Firearms designed for World War I flooded the streets, escalating violence.
  • "You can buy them anywhere... it's escalating the violence and it's making it easier for people to kill one another." – Jonathan Eig [29:34]
• No Immediate Gun Control Reforms:
  • Despite the horror, legislative change was slow and largely ineffective.

7. The Fall of Al Capone

[31:57–37:53]

• From Gangster to Public Enemy #1:
  • Unable to convict Capone for violent crimes, authorities built a case for tax evasion, a novel approach legitimized by recent Supreme Court rulings.
  • "Ultimately, they make the practical decision that it's better just to put him behind bars any way we can..." – Jonathan Eig [32:24]
• Capone’s Downfall – A Mixed Public Reaction:
  • Many saw him as a folk hero who provided what people wanted; juror bias against the IRS and sympathy for Capone were real concerns for prosecutors.
  • His trial was irregular, with a jury swap to ensure a conviction, after which Capone was sentenced to 13 years—the stiffest ever for tax evasion—and sent to Alcatraz.

8. Capone’s Final Years

[37:53–39:20]

• Only in his 30s when imprisoned, Capone’s health rapidly declined due to neurosyphilis.
• After his release, he lived quietly and out of the public eye, a far cry from his former infamy.

Notable Quotes & Memorable Moments

• On Prohibition’s Naivety:
  • “The government really thought that everyone would volunteer to just put away, to give up, pour down the drain, their fine bottles of wine and spirits and that everything would be happy...” – Jonathan Eig [05:45]
• On Press Coverage:
  • “This was definitely entertaining... news reporters from all over the world would come to Chicago and seek interviews with Al Capone, and he would grant them because he wanted to see himself as a celebrity.” – Jonathan Eig [13:50]
• On the Massacre Itself:
  • “Some cars pull up in front of the garage. Some of the neighbors said it looked like police cars... the men had been lined up against the wall of the garage and gunned down with machine guns and rifles and left there to die.” – Jonathan Eig [19:27]
• On Murder and Media:
  • “Why did this one turn people's stomachs? Why did it ignite this drive to get Capone and put him behind bars? It’s because of those photos in many ways.” – Jonathan Eig [21:06]
• On Prosecuting Capone:
  • "Are we going to be mocked for saying the only case we can make against him is he didn’t pay his taxes?... but it’s better just to put him behind bars any way we can." – Jonathan Eig [32:24]
• On Capone's Public Image:
  • “He would say, I’m just giving people what they want. I’m doing the same thing—when they serve drinks on Park Avenue, they call it hospitality. And with me, they call it a crime.” – Jonathan Eig [35:50]

Key Timestamps

| Timestamp | Segment / Topic | |-----------|---------------------------------------------------| | 01:22 | Atmospheric introduction to massacre and Prohibition Chicago | | 05:45 | Prohibition’s social and criminal consequences | | 08:06 | Violent gang rivalries, emergence of Capone | | 10:24 | Police corruption and inability to curb gang power| | 12:21 | Gang nicknames, media mythologizing crime | | 14:55 | Ethnic backgrounds shaping gang formations | | 17:44 | The massacre: set-up and confusion over planners | | 19:27 | Massacre details, survivor testimony | | 21:06 | Media’s new gruesome coverage shifts public perception | | 23:21 | Discussion on police (possible) involvement | | 25:01 | Aftermath: lack of leads, Hoover’s obsession | | 27:58 | Prohibition repeal; political angle | | 29:34 | Gun availability and rise in weapon lethality | | 31:57 | Capone’s arrest and prosecution for tax evasion | | 35:50 | Mixed public reaction to Capone’s conviction | | 37:53 | Capone’s demise and post-prison obscurity |

Tone and Style

The episode maintains a conversational, engaging tone with darkly cinematic flair—balancing sharp historical analysis with the grim drama of true crime. Jonathan Eig’s measured expertise is complemented by Maddie and Anthony’s quippy rapport and fascination with the period’s spectacle and moral ambiguity.

For Listeners Wanting More

Jonathan Eig’s work, especially "Get Capone," is referenced throughout and recommended for those seeking a deeper exploration of Prohibition Chicago. He also mentions a forthcoming biography of George Soros ([40:01]).

This episode is essential listening for anyone fascinated by the cross-section of American crime, politics, media, and legend-making. It not only examines the anatomy of one shocking event, but also how its myth and aftermath reverberate nearly a century later.