American History Tellers

Episode: St. Valentine's Day Massacre: Closing In On Capone | Part 3

Original Air Date: February 18, 2026

Host: Lindsey Graham

Guest: Jonathan Eig, author of Get Capone: The Secret Plot that Captured America's Most Wanted Gangster, Pulitzer Prize-winning biographer

Episode Overview

This episode dives into the aftermath of the notorious St. Valentine’s Day Massacre of 1929, widely attributed—though never proven—to Al Capone. Host Lindsey Graham and guest Jonathan Eig explore the complexities of the investigation, how federal authorities switched tactics to target Capone, and the myth versus reality of his legacy. The discussion covers the rise and fall of the infamous Chicago gangster, the mechanics behind his "untouchable" reputation, the strategy that finally landed him behind bars, and what happened to Capone after prison.

Key Discussion Points & Insights

The Mystery of the St. Valentine's Day Massacre

• Did Capone Order the Massacre?
  • Eig states it's one of America’s great unsolved crimes. "I think that there's a good chance that some of the guys around Capone were involved in it. But bottom line for me is that we still don't know." (Jonathan Eig, 02:29)
  • Multiple suspects, including Capone’s associates (e.g., Jack McGurn, “Killer” Burke), rival gangs (Purple Gang, Egan's Rats), and even potential police involvement.
• Alternative Theories
  • Eig recounts an FBI archive letter suggesting a crime of passion and police revenge, but no theory is definitive due to scant evidence. (03:44)

Societal and Political Impact

• Effect on the Federal Government
  • The massacre sparked public outrage, prompting Hoover to focus on crime and, notably, on “getting Capone” to demonstrate federal resolve. “He really became obsessed with Capone. Hoover would ask every member of his cabinet, what are we going to do to get Capone?” (Eig, 05:39)
  • The government leveraged public sentiment to intensify efforts, despite Capone’s declining criminal power. (04:52-06:46)

Capone’s Business Empire and Methods

• The Outfit and Its “Chaos”
  • Capone’s operation was sprawling, improvisational, and depended on managing chaos. He didn’t own businesses outright; he took cuts and operated as a loose, decentralized hub.
  • His “tolerance for chaos” proved valuable, ducking law enforcement by avoiding paperwork and relying on an all-cash business.
    “The chaotic nature of his business actually becomes a strength because it's almost impossible to prove that he's involved in anything.” (Eig, 09:58)

Capone’s Celebrity and Public Image

• Crafting the Robin Hood Myth
  • Capone cultivated a favorable public image by positioning himself as a provider and protector—a “regular guy” supporting the community, even running soup kitchens during the Depression.
  • “He's providing jobs… spreading bribes around as well.…The crime was a part of the allure.” (Eig, 14:40)
  • Proactively sought media attention, even inviting women’s magazines for interviews: “I'm just giving the people what they want. It's hospitality when they do it on Park Avenue, but they call me a criminal for doing the same thing.” (Eig, 13:04-14:20)
• Capone’s Charisma vs. Strategy
  • Eig sees his PR as both strategy and genuine personality: “It's both… he's really trying to earn sympathy.” (15:41)

The Turning Point: Federal Tactics

• Illegal Income as Taxable (1927 Supreme Court Ruling)
  • Supreme Court ruling opened the door to prosecuting criminals for tax evasion—a crucial legal change that set the stage for Capone’s takedown. (17:37)
• Rise of George E. Q. Johnson
  • Honest and unbribeable, U.S. Attorney Johnson was tasked to “get Capone, whatever it takes”. (18:24)
  • Johnson’s archived notes revealed the government bent rules and made questionable calls to ensure Capone’s conviction. “If Capone had the right lawyer…the entire case would have been thrown out.” (20:02)

Capone’s Downfall: The Tax Evasion Case

• Accidental Confession
  • Capone tried to cut a deal, submitting a letter admitting to income. His lawyers should’ve protected him with proper disclaimers but failed. The IRS used this letter to build a case. (21:11-22:31)
• Frank Wilson—the Unsung Investigator (23:01)
  • Wilson, a Revenue Bureau accountant, found a crucial ledger referencing “Al,” connecting Capone to illicit income.
  • Pressured witnesses and pieced together spending evidence when hard proof was scarce. “Frank Wilson wasn't just an accountant … got to do a little more traditional police work.” (24:49)
• Race Against Statute of Limitations
  • Johnson secured an indictment just two days before the tax charges would expire. “It was a close call.” (26:22)
• Failed Plea Deal
  • Capone’s lawyers negotiated a plea-bargained sentence; Judge Wilkerson, under political and public pressure, abruptly rejected it, opting for a jury trial.
    “Capone had agreed to two and a half years. …Wilkerson said, no, I'm not happy with this. …We're going to trial.” (28:16)
  • Judge’s jury swap replaced possibly bribed jurors with honest, rural Chicagoans, “every time the jurors came into the courtroom, it smelled like turnips and hayseed.” (29:40)

The Trial and Aftermath

• Weak Government Case and Capone’s Own Lawyers
  • Prosecution relied on circumstantial evidence (spending patterns). Capone’s lawyers failed to object properly, compounding his legal troubles.
  • “They build a case by showing Capone's spending ... it's requiring a leap of faith, and that's the leap of faith that the jury is willing to make.” (31:13)
• Sentencing and Prison
  • Capone expected a short sentence; Judge imposed 11 years—far more than anticipated.
    “So when he was sentenced to 11 years, you could imagine he was stunned.” (32:20)
• Decline and Legacy
  • Capone left prison mentally and physically diminished by syphilis, living out his days in isolation. Speculation continues about missing millions—but Eig suspects he spent or gave away most of it.
    “Those last years were really just spent alone…and in January 1947, he dies. He's only 48 years old.” (33:15-35:24)

The Broader Lesson

• Legacy for Law Enforcement
  • The “Capone style case” (prosecution on a technicality) became a model for future law enforcement strategy, focusing on getting dangerous individuals off the streets however possible.
    “The real lesson is they found a technicality, they got him off the streets, and it served in many people's view of the public good.” (35:30-36:24)

Notable Quotes & Memorable Moments

• On the Unresolved Crime:
  "It's one of the greatest unsolved crimes in all of American history."
  — Jonathan Eig (02:29)

• On Capone’s Chaotic Shield:
  “The chaotic nature of his business actually becomes a strength because it's almost impossible to prove that he's involved in anything.”
  — Jonathan Eig (09:58)

• Capone’s P.R. Mindset:
  “I'm just giving the people what they want. It's hospitality when they do it on Park Avenue, but they call me a criminal for doing the same thing.”
  — Jonathan Eig (14:20)

• On the Trial:
  “They're saying to the jury, we don't know how he made his money, but we know he's got money. And if he's got money, he should have paid taxes on it, and he didn't.”
  — Jonathan Eig (31:13)

• On Law Enforcement's Lesson:
  “The real lesson is they found a technicality, they got him off the streets, and it served in many people's view of the public good.”
  — Jonathan Eig (36:24)

Timestamps for Important Segments

• 02:29 – Did Capone order the massacre?
• 04:52 – St. Valentine’s Day Massacre’s effect on government
• 07:05 – Capone’s criminal empire and business practices
• 13:04 – Capone’s public image and working the press
• 17:37 – Key legal pivots: taxable illegal income, rise of George E. Q. Johnson
• 23:01 – Frank Wilson and the importance of the ledger
• 26:22 – Indictment narrowly beats statute of limitations
• 28:11 – Judge Wilkerson rejects plea deal, changes jury
• 31:13 – Weak evidence and the government’s narrative at trial
• 32:20 – Capone’s sentence and reaction
• 33:15 – Life after prison and Capone’s legacy
• 35:30 – Capone’s case as a model for future prosecution tactics

Tone & Style

• Conversational, accessible, and rich with anecdotes.
• Blend of investigative detail, colorful quotes, and historical narrative.
• Both host and guest display a sense of curiosity and dry wit throughout the episode.

For Further Listening

The episode is the final part in a three-part series on the St. Valentine’s Day Massacre and is followed by a new series on Great American Authors.

Summary prepared by podcast summarizer | Content up-to-date as of February 18, 2026