Capone orchestrated the most notorious gangland killing of the century, the 1929 St. Valentine's Day Massacre in the Lincoln Park neighborhood on Chicago's North Side. Although details of the killing of the seven victims in a garage at 2122 North Clark Street are still in dispute and no one was ever indicted for the crime, their deaths are generally linked to Capone and his henchmen, especially Jack "Machine Gun" McGurn. McGurn is thought to have led the operation, using gunmen disguised as police and toting shotguns and Thompson submachine guns.
The massacre was Capone's effort to dispose of organized crime rival "Bugs" Moran. The North Side gang had become increasingly bold in hijacking the Outfit's booze trucks and encroaching on the South Side and Capone was ready to put it to an end.
After all efforts to secure a truce had failed, Capone, his accountant/chief extortionist Jake "Greasy Thumb" Gusik, and Frank "The Enforcer" Nitti agreed that they'd have to risk the political heat that would come from wiping out Moran and his gang or face eventual elimination at the hands of the North Siders. They assigned the task to McGurn and told him to use "outside torpedoes" to avoid implication. McGurn secured the services of triggermen from New York, Tennessee, Detroit, and downstate Illinois.
They rented an apartment across from the Clark Street trucking garage that served as a Moran headquarters to monitor their targets' habits and movements and placed a call to the garage offering to sell a truckload of whiskey stolen by freelancing Sicilian immigrants from a Capone shipment. Such freelancers often hijacked such shipments from both gangs and sold them to the highest bidders, so no suspicions were aroused in the Moran camp. The stolen booze (high-grade Canadian whiskey) was brought to the garage, and the deal was done.
As hoped, the entire Moran gang was there. Unknown to the North Siders, these "freelancers" were being paid by McGurn to set them up for the kill. On February 13, the freelancers called again and set up another transaction for the next day. The freelancers were expected to drive the truck right into the garage, where McGurn hoped the entire Moran gang would again be assembled. At the set time, a stolen Chicago police car pulled up and uniformed "officers" entered the building, along with others who had been standing nearby.
Apparently, the gang members thought that they had been scammed and that they had been set up for a raid. They sheepishly lined up to cooperate in the belief that their lawyers would fix things downtown, as they had many times before. Moran arrived 10 minutes late, spotting what he thought to be a police car outside, decided to keep walking and did not enter the garage.
It is believed that a local optometrist was also one of the victims, an innocent bystander and not part of Moran's gang. The optomestrist, who supplemented his income through bootlegging and liked to hang out at the garage with the gang members, had been mistaken that morning for Moran because he was of similar height and wore the same color gray hat and coat favored by the North Side chieftain. After the supposed Moran entered, the lookouts triggered the "raid." At the last moment one of the gang-members realized that Chicago police officers never carried machineguns, but it was too late.
Forensic evidence shows that the seven victims were almost cut in two by machine gun fire and that many of the victims had their faces shot off by shotgun blasts for good measure. The photos would cause public sympathy to fall out of Capone's favor, and federal law enforcement to focus more closely on investigating Capone's activities.
However, the local police turned the other way in regards to the events. They made no real efforts to solve the crime or delve further into the killings. People in the neighborhood saw the police go in and heard what they thought were a series of backfires, which were common at a garage. The "police" later led some men out to the car and left.
The grisly scene was discovered after the mechanic's dog began to howl so loudly that neighbors went in to see what was wrong. Frank Gusenberg, a member of the Moran gang, survived long enough to be questioned in a hospital before he died. However, when asked "Who shot you?" Frank replied, "Nobody shot me," denying any justice on the murderers.
Although Moran escaped, all his chief deputies were killed and his illegal liquor operation in Chicago rapidly declined. When asked by reporters if he believed Capone was behind the killings, Moran scornfully replied "Only Capone kills like that!"
An indignant Capone countered, "Oh yeah! Listen … they don't call that guy 'Bugs' for nothing!" in a reference to Moran's reputation for savagery. With his remaining resources, Moran marked Capone and his key underlings for extermination.
Capone arranged to have himself jailed in Philadelphia for a year to avoid numerous "murder for hire" outfits that were hunting for him. McGurn was gunned down at a bowling alley on the anniversary of the garage slaughter, and two others involved in the killing disappeared.
Moran eventually ran out of resources and fled to Ohio, allowing Capone to return to Chicago, where he quickly found himself in the legal quagmire that effectively removed him from power. It is generally thought that Capone precipitated his own decline with the garage killings. Graphic photos of bodies lying in pools of blood were plastered all over the papers.
A secret convocation of Chicago civic leaders initiated an all-out effort to drive Capone from power. Nevertheless, had Capone and his gang done nothing, the North Side gang likely would have succeeded in killing their rivals and taking over the entire city. Moran and his associates were driven by a visceral hatred of the "South Side Scum," whom they considered to be sexual deviants and degenerates who dealt in prostitution and drug peddling and allowed debased jazz musicians to play in their bars.
Moran had also repeatedly vowed to avenge the deaths of his close friends and mentors O'Banion and Weiss (the latter being gunned down on the steps of Trinity Cathedral). It is said that Nitti became enraged with McGurn (whom he considered to be a rival) over Moran's escape and the unfavorable publicity that ensued.
What was left of Bugs Moran's crew after the shooting.