The St. Valentine’s Day Massacre

Capone ordered the massacre to eliminate his rival Bugs Moran and take full control of Chicago's organized crime. The feud had been escalating for years, with Moran orchestrating the murder of Capone's ally Patsy Lolordo and plotting against Capone himself. Capone tasked his trusted enforcer Jack McGurn with the job, wanting Moran dead regardless of whether his lieutenants also perished in the process.

Earlier flashbacks show Capone's men eliminating O'Banion and Hymie Weiss, establishing a pattern of violent retaliation.

Capone retreated to his winter home in Miami specifically to establish a public alibi while the violence unfolded in Chicago. By being seen in Miami on February 14, 1929, he distanced himself from the direct planning and execution of the massacre. This was a strategic move to avoid direct suspicion and maintain plausible deniability despite personally ordering the hit through McGurn.

The film shows Capone deliberately choosing to leave Chicago before the massacre, emphasizing his calculated decision to create an alibi.

Moran avoided the garage because he sensed danger. He had become increasingly paranoid about his safety and typically avoided predictable locations. On the morning of February 14, he stopped at a diner instead of going directly to the garage, which saved his life. When the shooting started, he realized too late that he had narrowly escaped the ambush.

Earlier scenes show Moran's growing paranoia and his tendency to change plans unexpectedly, hinting at his survival instinct.

Five of Moran's gang members were killed: Frank and Peter Gusenberg, Adam Heyer, Reinhard Schwimmer, and Frank Gusenberg's brother. All were longtime associates of Moran's North Side Gang. Two additional victims were bystanders caught in the crossfire: Johnny May, a young man who worked at the garage, and Reinhard Schwimmer, who was partially deaf and didn't react quickly enough to escape.

The film establishes these men as Moran's core crew who regularly met at the garage, making them logical targets.

Moran was driven out of Chicago following the massacre as Capone's dominance became absolute. He continued operating from outside the city for several years but was eventually arrested and imprisoned at Leavenworth. He died of lung cancer in Leavenworth in 1957, having never been charged for the St. Valentine's Day killings. He maintained silence about the murders until his death.

The film foreshadows Moran's downfall by showing his weakened position immediately after losing his key men.

The disguises served a tactical purpose: they allowed the gunmen to enter Moran's garage without raising immediate alarm. By posing as police conducting a raid, the four men dressed as officers gained entry and convinced the victims to line up against the wall with their hands up. This approach minimized resistance and maximized the element of surprise before the real shooters with Tommy guns opened fire.

Earlier attacks in the film, like the Hawthorne Hotel ambush, show that timing and deception were central to Capone's hit strategies.

Joe Aiello was a low-level mafioso whom Moran recruited to help him remove Patsy Lolordo, a Capone ally who controlled Sicilian interests in Chicago. Moran promised to replace Lolordo with an envoy more favorable to his own operations. Aiello carried out the hit on Lolordo, but Capone retaliated by having Aiello killed while he was fleeing the state on a train. This alliance ultimately proved fatal for both men.

The timeline shows Moran plotting Lolordo's removal specifically to weaken Capone's influence before the massacre.

No one was charged because the witnesses were too terrified to testify, the killers either vanished or were themselves killed in retaliatory violence, and police corruption prevented meaningful investigation. Additionally, the two actual triggermen who entered with Tommy guns were never positively identified. The case became a cold case almost immediately, and the mystery of the shooters remains partially unsolved to this day.

The film shows the immediate aftermath where witnesses refuse to cooperate with police, setting the stage for impunity.

Capone continued to dominate Chicago's underworld for several more years until his arrest in 1940 for tax evasion. He was sentenced to eleven years in federal prison, including time at Alcatraz. After his release in 1947 due to declining health, he died in 1947 from complications of syphilis. Like Moran, he was never prosecuted for the actual murders connected to the massacre or the broader gang war.

The film hints at Capone's eventual downfall through his imprisonment, showing the beginning of his legal troubles.

Peter and Frank Gusenberg, Moran's top enforcers, were among the five gang members killed in the garage. They were among the last to arrive and were ordered to line up against the wall by the disguised gunmen. Both were shot multiple times with Tommy guns, and Frank was killed instantly. Peter was wounded but still alive when the gunmen checked for survivors and finished him off with a shotgun blast to ensure no one survived.

Earlier scenes establish the Gusenberg brothers as Moran's primary muscle and frequent visitors to the garage, making them primary targets.

Capone ordered the execution of Scalise and Anselmi because he learned they had been planning to betray him and kill Moran in order to take over the gang themselves. After eliminating Moran's rivals in the massacre, Capone could not tolerate disloyalty within his own ranks. He had the two men killed in a coordinated hit that demonstrated his willingness to purge any threat to his authority, even from his own men.

The film establishes Scalise and Anselmi as ambitious subordinates who chafed under Capone's leadership.