With Colosimo dead, Torrio began moving into the bootlegging business and promoted Capone to be his right-hand man. Together, the two set to work cornering the market on illegal booze in the city. Thier efforts put them at odds with the rival North Side gang headed by Irish gangster Dean O’Banion, which was heavily involved in the bootlegging racket. Soon, the competition led to war. In 1924, O’Banion was murdered, likely by Frankie Yale. In revenge, a group of North Side gunmen attacked Capone, but he escaped unharmed. Torrio wouldn’t be so lucky. Two weeks later, he was ambushed and shot several times.
Torrio survived his injuries, but the attack left him shaken. Once out of the hospital, he left for Italy, leaving Capone in charge of the Chicago operation. Torrio always preferred to stay out of the spotlight, conducting his gang’s illegal activities in the shadows. Capone shared little of his mentor’s subtlety. Once in control, Capone began cultivating an image as a celebrity. His organization was bringing in millions through the bootlegging trade and Capone spent it on flashy suits and jewelry. He made no effort to avoid the press, instead giving reporters veiled references to his work as a “businessman” who was “giving people what they want.”
Capone became a prominent figure in the debate on Prohibition. To many, he was a simple thug. However, others believed he was taking a stand against an unjust law. But what many of his supporters neglected to mention was that all of Capone’s operations were supported by extreme violence. Capone regularly orchestrated bombing campaigns and assassinations against anyone who threatened his control over the booze supply in Chicago. And soon, his ongoing war with the North Side gang would result in a horrific massacre that even Capone’s staunchest supporters couldn’t ignore.
On February 14, 1929, five members of the North Side gang and two of their associates were stopped by men wearing police uniforms in the Lincoln Park neighborhood of Chicago. The men were led to a nearby garage, where they were lined up against a wall and brutally gunned down. The press soon dubbed the event the “St. Valentine’s Day Massacre.” There was no hard evidence in the case to go on. The one victim still alive when the real police showed up stuck by the gangster code of silence and stated, “no one-shot me,” before dying of multiple bullet wounds. However, suspicion immediately fell on Capone.
The public soon began clamoring for justice against the city’s most notorious gangster. But protected by a web of corruption and bribes, Capone was able to avoid any charges of murder or violating Prohibition. Instead, the government focused on a lesser charge. And in 1932, Capone was finally sent to prison for failure to pay income tax. Many people saw this as another instance of Capone escaping justice for his murders. But once in prison, he suffered through his own form of punishment as he began receiving visits from the ghostly shade of one of his victims and slowly descending into madness.