Al Capone: The Chicago Outfit · 6 Sep 2026 · 13 min

Scarface to Alcatraz: The Full Rise and Ruin of Al Capone

From Brooklyn street kid to the most powerful mob boss in American history, Al Capone built a hundred-million-dollar empire on Prohibition's broken promise — then lost everything to the tax code and syphilis. This chapter traces the complete arc: Cicero, the St. Valentine's Day Massacre, Eliot Ness, and a broken man dying in Miami.

Al Capone: The Chicago Outfit
Now Playing
Scarface to Alcatraz: The Full Rise and Ruin of Al Capone

Audio is available on Spreaker — see link below.

What's covered

The Brooklyn Boy Who Would Run Chicago

Here's what most people get wrong about Al Capone. They think he was brought down by Eliot Ness.

Listen now →

Building the Empire

By nineteen twenty-four, Capone was no longer just running errands. Torrio had expanded aggressively across Chicago's South Side, and Capone had become essential to that expansion.

Listen now →

Valentine's Day and the Beginning of the End

February fourteenth, nineteen twenty-nine. Seven members of Bugs Moran's North Side Gang were standing in a garage at twenty-one twenty-two North Clark Street.

Listen now →

The Tax Case No One Believed Would Work

The logic of the tax prosecution was elegant in a way that infuriated gangsters. Capone had made millions.

Listen now →

Atlanta, Alcatraz, and the Disease That Waited

Capone started his sentence at the federal penitentiary in Atlanta. True to form, he initially found ways to make the environment comfortable, securing privileges and easing his conditions through whatever influence he could apply.

Listen now →

Palm Island and the Final Years

The Palm Island house in Miami was beautiful. Waterfront property, a pool, a place that in different circumstances might have signaled success and arrival.

Listen now →

Chapter summary auto-generated from the verified script. Listen to the full episode for the complete content.

More episodes

From Al Capone: The Chicago Outfit