Merciless Murder: A True St. Valentine's Day Tale

St. Valentine's Day in Chicago rocks in any year ... but a twist of fate and a hail of machine-gunfire in Chicago, on February 14, 1929, blew this town onto the front pages of newspapers worldwide, and marked the beginning of the end of the Al Capone Gangster Rule that still thrills and fascinates millions of Americans.

Ironically, Capone himself was only peripherally involved in this bloody and shocking skirmish in the gang war that killed seven men - one of them an innocent bystander - and set the feds on his scent for good.

Chicago police, and eventually Capone's once-adoring public, were outraged by the St. Valentine's Day Massacre's ingenious sleight-of-hand, contrived by Capone's vicious right-hand man, Jack "Machine Gun" McGurn, a gangster known for his cold heart, love of the Tommy Gun, and long memory for real or imagined wrongs.

McGurn was able to pull off this hugely violent, very public gangland murder in broad daylight on a busy Chicago street by using killers dressed as members of the Chicago Police Department, driving a decked-out Chicago police car, to wipe out a group of his rivals.

Gangland Vengeance

It's widely believed that McGurn instigated the slaughter in hopes of assassinating George "Bugs" Moran, a fellow bootlegging gangster who ran the famed Chicago Northside O'Banion organization after O'Banion's own assassination five years earlier.

The O'Banion organization had been at war with the Cicero-based Capone group for years, and Capone blamed the Northsiders for periodically hijacking liquor shipments meant for Capone's gang. In the midst of a widespread and violent Chicagoland gang war, two of Moran's henchmen - the Gusenberg brothers - had nearly killed McGurn in an earlier hit in a public phone booth, and Capone's man craved revenge.