The St. Valentine’s Day Massacre

In the Roaring Twenties, Chicago becomes a battlefield of organized crime as two mighty gangs clash for control. The Southside Gang, led by the infamous Al Capone, pushes back against George “Bugs” Moran and his North Side outfit, both aiming to dominate bootlegging, gambling, and the protection racket that fuels their power. Moran’s inner circle includes Peter Gusenberg and the ruthless [Frank Gusenberg], who pressure speakeasy owners into doing business with them. The dynamics of loyalty and money put strain on Moran’s camp, especially as his moll Myrtle becomes entangled in the web of extravagant spending that sparks tension within Peter’s ranks.

The feud deepens with a deadly history of revenge. Capone remembers Hymie Weiss’s bid to kill him, a memory that unfolds in flashbacks of the September 1926 lunchtime ambush at Cicero and the earlier elimination of North Side leader Dean O’Banion in 1924, followed by Weiss’s own demise in 1926. These past strikes feed the present cunning as Capone’s men recalibrate their strategy. Moran, in turn, schemes with low-level mafiosi like Joe Aiello to remove Patsy Lolordo, a close Capone ally who represents Sicilian interests in Chicago, hoping to replace him with a more Moran-friendly envoy. Patsy Lolordo is targeted, his bodyguards compromised, and he is murdered in his apartment, sending a sharp message through both gangs. Capone responds by personally hunting down Aiello, who is killed while fleeing the state.

The playing field shifts as McGurn’s plan edges toward action. With Moran’s men growing bolder, Capone retreats to his winter home in Miami to maintain an alibi and keep the gang war from igniting into outright chaos. On a February morning in 1929, Capone’s outfit stages a brazen assault: four henchmen dressed as police officers raid Moran’s northside garage, while two more storm in armed with Tommy guns. The hit wipes out five of Moran’s men, using shotguns to erase any survivors, and two bystanders—Johnny May and Reinhard Schwimmer—are killed in the crossfire. Moran, not present at the garage, slips away to a diner, sensing the danger too late for a direct confrontation.

“Only Capone kills like that,” Moran remarks in a hospital press conference, a jolt of public accusation that echoes the chaos unfolding back in Chicago as Capone, also in the press, dismisses Moran’s claims of wit and strategy.

The fallout echoes beyond the garage. Capone’s men move to quell the betrayal within their ranks, targeting John Scalise and Albert Anselmi for their alleged plans to defy him. Moran is driven out of Chicago in the years that follow, eventually dying of lung cancer while in Leavenworth, his legend sheltering behind a wall of silence. Capone, after a prison stint on Alcatraz, passes away from complications of syphilis. In the end, no one is ever brought to formal justice for the murders that sparked the war; the killers simply fade away or vanish, leaving a city with a memory of a night when whole blocks trembled under the weight of gang ambition.

A sprawling, violent tableau of loyalty, betrayal, and power, the story threads together a web of personal feuds, political entanglements, and brutal hitwork that reshaped Chicago’s underworld. From the initial spark of rivalries to the cold calculus of assassinations and counter-moves, the era’s brutality is laid bare, with scenes that linger in the mind—whether through the memory of the Hawthorne Hotel confrontation in Capone’s past, the chilling precision of the garage assault, or the quiet tragedy of Moran’s final years behind bars. The film never-shy from harsh consequences, it keeps the focus tight on the characters who drove the blood-soaked feud and the myths that grew around their ruthless, relentless pursuit of absolute control.

Last Updated: October 05, 2025 at 11:39