At 10:30 a. m. on Saint Valentine’s Day, February 14, 1929, four men—two wearing police uniforms and two in suits, ties, overcoats, and hats—walked into a garage at 2122 North Clark Street in Chicago’s Lincoln Park neighborhood. Within minutes, seven men were dead, shot with weapons that included two Thompson submachine guns.
Witnesses then saw the uniformed men leading others at gunpoint out of the garage. The massacre marked the climax of a brutal five-year gang war between rival bootlegging organizations and ultimately triggered a federal crackdown that brought down both sides. The North Side Gang, like many Chicago prohibition-era outfits, traced its roots to the Market Street gang, a collection of pickpockets, sneak thieves, and labor sluggers operating in the city’s 42nd and 43rd wards. The gang rose to prominence during the early 1910s newspaper circulation wars between the Chicago Examiner and the Chicago Tribune.
Future North Side leader Charles Dean O’Banion, then a member of the juvenile satellite gang Little Hellions, made valuable political and journalistic contacts during those years. When Prohibition began, O’Banion and other Market Street veterans turned to bootlegging. The North Siders quickly seized control of existing breweries and distilleries on Chicago’s north side, giving them a near monopoly on genuine beer and high-quality whiskey while competitors were left with rotgut liquor and moonshine. Beyond bootlegging, the gang continued burglaries and ran illegal gambling operations, though they refused to engage in prostitution, unlike their rivals.
O’Banion strengthened his political position by assisting politician friends and engaging in election fraud. He also ran a public relations campaign, donating large sums to orphanages and charities and providing food and loans to the poor and unemployed. Tensions between the North Siders and the South Side Chicago Outfit escalated over old Irish-Italian animosities and O’Banion’s refusal to sell portions of North Side distilleries to South Siders. In early 1924, Johnny Torrio brokered an alliance between O’Banion and Al Capone.
The alliance began to unravel when O’Banion demanded that Angelo Genna pay a $30,000 gambling debt from losses at the gang’s casino. The demand violated an agreement allowing Genna and other gang members to incur debts there. Torrio persuaded Genna to pay the debt to keep the peace. Torrio’s patience ran out when O’Banion offered to sell him the valuable Sieben Brewery, then arranged for police to raid and arrest Torrio while he was inspecting the property.
After his release from custody on November 10, Torrio complied with the Genna crime family’s demand to have O’Banion killed. Shortly after the death of Mike Merlo, Frankie Yale, John Scalise, and Albert Anselmi allegedly entered O’Banion’s Scofield flower shop and shot him dead. Hymie Weiss assumed leadership of the North Side Gang and immediately retaliated. Weiss, Bugs Moran, and Vincent Drucci attempted to assassinate Capone on January 12, 1925, at a Chicago South Side restaurant, shooting at his car and hitting the chauffeur but missing Capone entirely.
Unnerved, Capone ordered construction of his famous armored car. The North Siders also kidnapped one of Capone’s trusted bodyguards, tortured him for information, then executed him and disposed of his body. On January 24, Weiss, Moran, and Drucci ambushed Torrio as he returned from shopping with his wife. Torrio and his chauffeur, Robert Barton, were both wounded multiple times.
Moran’s gun misfired as he was about to kill Torrio, forcing the gang members to flee as police arrived. Having narrowly survived, Torrio decided he wanted out. After serving time on bootlegging charges, he retired to Italy, handing leadership of the Chicago Outfit to Capone. The North Siders then targeted the Genna brothers.
Moran shot and killed Angelo Genna after a car chase. Mike Genna was killed by police after turning his gun on them following a shootout with the North Siders. Drucci assassinated Samuzzo Amatuna, a Genna family supporter. Antonio “the Gentleman” Genna was eventually assassinated, though it was rumored Capone, not Weiss, ordered that killing.
The remaining Genna brothers fled Chicago. With the Genna family gone, Torrio out of the rackets, and Capone on the defensive, the North Siders expanded their business and plotted another attack. A fleet of North Side cars led by Moran drove to Capone’s hotel in Cicero. They drove past the lobby and opened fire with Thompson submachine guns while Capone and his bodyguard were drinking downstairs, forcing them to take refuge on the ground floor.
After the attack, Capone told the North Siders he desired a truce. A truce was reached but inevitably fell apart. Capone retaliated by assassinating Weiss and several associates. Drucci and Moran became co-leaders of the North Side Gang.
For several months, the two gangs traded killings and bombings until a peace conference was held. During the conference, Capone complained that the gangs were making “a shooting gallery of a great business. ” He argued that Chicago should be seen as a pie and each gang should get a slice. The two gangs agreed to reconcile.
Not long after, Drucci was killed in a brawl with police, and Moran became sole leader. The conflict soon reignited. Moran had two union leaders executed because they were powerful allies and personal friends of Capone. That act prompted Capone to carry out what became known as the Saint Valentine’s Day Massacre.
Frank Gusenberg, the only Survivor of the garage shooting, died hours later at a nearby Chicago hospital after refusing to name his assailants. The primary target, North Side Gang leader Bugs Moran, was not at the garage and escaped unharmed. The identities of the four gunmen remain unknown to this day. The attack effectively ended the five-year gang war between Capone and Moran.
But the sheer audacity of the crime prompted a federal crackdown on all gang activity in Chicago, ultimately leading to the downfall of both Moran and Capone.