St. Valentine's Love & Massacre

About this episode

This episode explores the dark history of Valentine's Day and the infamous St. Valentine's Day Massacre.

This week on The Parallax Podcast , Karisa and Willow explore the razor-thin line between love and violence, tracing the twisted history of Valentine's Day from ancient ritual to infamous massacre. Karisa begins by unearthing the surprisingly dark and tangled origins of Valentine's Day. She traces its roots from the raucous Roman festival of Lupercalia —a day of fertility rites and ritual sacrifice—through the murky legends of martyred saints, to its eventual transformation into a celebration of courtly love and commercial romance. Then, Willow shifts the mood from the poetic to the perilous, recounting one of the most notorious mob hits in American history: The St. Valentine's Day Massacre . On February 14, 1929, in a Chicago garage, seven men were lined up and executed by gunmen dressed as police—a brutal power play in Al Capone's war for control of the city's underworld. Willow breaks down the chilling details of the ambush, the bloody aftermath, and how this single morning of violence came to symbolize the ruthless era of Prohibition-era gangland warfare. From pagan rites to Prohibition hits, this episode reveals how one date on the calendar has forever held space for both…

People in this episode

Hosts: Karisa DeLay, Willow Grace

Topics covered

• Valentine's Day origins
• mob history
• true crime
• gang violence
• Prohibition
• love and violence

Keywords

• Valentine's Day origins
• Lupercalia
• St. Valentine's Day Massacre
• Al Capone
• Chicago mob
• Prohibition
• true crime
• holiday history
• gang violence

Mentioned in this episode

Organizations: Al Capone

Books & works: Valentine's Day

Places: Chicago

More episodes of The Parallax Podcast

• To Time Travel or Not to Time Travel · June 5, 2026 · 1h 17m
• A Hard Pill to Swallow: The South Korean Supplement Scandal & The Ancient Echo of Child Sacrifice (Part 2) · May 15, 2026 · 58 min
• A Hard Pill to Swallow: The South Korean Supplement Scandal & The Ancient Echo of Child Sacrifice (Part 1) · May 8, 2026 · 1h 2m
• The Ghost Cats of Appalachia & Felines of the Ancient World · March 27, 2026 · 44 min
• The Lady in White: A Philippine Encounter & The World of Spectral Sightings · March 20, 2026 · 47 min
• The Blobs of Oakville · February 20, 2026 · 44 min