On February 14, 1929, seven men were lined up against a garage wall on North Clark Street — and Al Capone's Chicago empire peaked and began to crack in a single morning. This chapter traces the full arc: Brooklyn origins, the Cicero takeover, the St. Valentine's Day Massacre, and the North Side war that made Capone untouchable in legend but exposed him in reality.
Audio is available on Spreaker — see link below.
On the morning of February fourteenth, nineteen twenty-nine, George "Bugs" Moran was running late. A few minutes.
Al Capone wasn't born into the Chicago rackets. He was born in Brooklyn in eighteen ninety-nine, the son of Italian immigrants who had made the crossing with nothing.
Prohibition had handed Chicago's underworld an extraordinary gift. The Eighteenth Amendment banned alcohol but didn't reduce demand for it by a single drink.
The one thing Capone couldn't fully control was the North Side. The Irish and Polish gangs who'd operated there before Prohibition weren't willing to surrender territory.
The photographs from the Clark Street garage appeared in newspapers across the country. Seven bodies.
The approach that ultimately worked was one the underworld never took seriously. Capone didn't file income tax returns.
Prison didn't go the way Capone expected. At Atlanta initially, he attempted what had worked for him everywhere else: money changing hands, arrangements made, relative comfort purchased.
The Valentine's Day Massacre sits at the center of the Capone story for a reason. It's the hinge point.
Chapter summary auto-generated from the verified script. Listen to the full episode for the complete content.