A crackdown on racketeering in Chicago meant that Capone’s first mobster job was to move operations to Cicero. With the assistance of his brothers Frank (Salvatore) and Ralph, Capone infiltrated the government and police departments. Between them they took leading positions within Cicero city government in addition to running brothels, gambling clubs and racetracks. Capone kidnapped opponents’ election workers and threatened voters with violence. He eventually won office in Cicero but not before his brother Frank had been killed in a shoot out with Chicago’s police force.
Capone had prided himself on keeping his temper under wraps but when friend and fellow hood Jack Guzik was assaulted by a small time thug, Capone tracked the assailant down and shot him dead in a bar. Due to lack of witnesses, Capone got away with murder, but the publicity surrounding the case gave him a notoriety that he had never had before.
After the attempted assassination of Capone’s friend and mentor Johnny Torrio the frail man left his legacy of nightclubs, whorehouses, gambling dens, breweries and speakeasies to Capone. Capone’s new found status saw him moving his headquarters to the luxurious Metropole Hotel as part of his personal crusade to become more visible and to court celebrity. This included fraternising with the press and being seen at places like the opera.
Capone was different from many gangsters who avoided publicity. Always smartly dressed, quiet and with political nous, he set out to be viewed as a respectable businessman and pillar of the community.
Capone’s next mission involved bootlegged whiskey. With the help of his old friend Frankie Yale in New York, Al set out to smuggle huge quantities into Chicago. The events would lead to what became known as The Adonis Club Massacre where Capone had Yale’s enemies brutally attacked during a Christmas party.
Capone’s bootlegging whiskey trail from Chicago to New York was making him rich, but an incident involving Billy McSwiggin, known as the "hanging prosecutor", was to prove a major setback for the unassailable gangster.
McSwiggin was mistakenly shot and killed by Capone’s henchmen during a shoot out between rivals outside a bar. Capone was blamed but once again due to lack of evidence he escaped arrest. However, the murder was followed by a big outcry against gangster violence and public sentiment went against Capone.
High profile investigations against Capone failed. The police therefore took their frustrations out by constantly raiding his whorehouses and gambling dens. Capone went into hiding for three months during the summer. But eventually he took a huge risk and gave himself up to the Chicago police. It proved to be the right decision as the authorities did not have enough evidence to charge him. Capone was a once again a free man having made a mockery of the police and justice system.
Ironically, Capone took on the role of peacemaker, appealing to the other gangsters to tone down their violence. He even managed to broker an amnesty between rival gangsters and for two months the killing and violence ceased.
But Chicago was firmly in the grip of gangsters and Capone appeared beyond the reach of the law. Somewhat ironically it was the pen pushers from the tax office who were to pose the greatest threat to the gangsters’ bootlegging empires. In May 1927, the Supreme Court ruled that a bootlegger had to pay income tax on his illegal bootlegging business. With such a ruling it wasn’t long before the small Special Intelligence Unit of the IRS under Elmer Irey was able to go after Al Capone.
Capone left for Miami with his wife and children and bought Palm Island estate, a property that he immediately started to renovate expensively. This gave Elmer Irey his chance to document Capone's income and spending.
But Capone was clever. Every transaction he made was on a cash basis. The only exception was the tangible assets of the Palm Island estate, which was evidence of a major source of income.
Meanwhile, internal infighting between rival gangsters escalated into street violence and frequent hijackings of Capone’s whiskey transports became a big problem.
Another thorn in the side for Capone was Frank Yale. Once a powerful associate, he was now seen as the main instigator of disruptions to Capone’s whiskey business. One Sunday afternoon, Yale met his end with the first use of a ‘Tommy gun’ against him.
Capone also had to deal with rival gangster Bugs Moran and his North Siders gang. They had been a threat for years. Moran had even once tried to kill Capone’s colleague and friend Jack McGurn. The decision by Capone and McGurn to avail themselves of Moran was to lead to one of the most infamous gangland massacres in history – The St Valentine’s Day Massacre.
On Thursday, 14 February 1929 at 10.30am Bugs Moran and his gang were lured by a bootlegger into a garage to buy whiskey. McGurn's men would be waiting for them, dressed in stolen police uniforms; the idea being that they would stage a fake raid. McGurn, like Capone, made sure he was far away and checked into a hotel with his girlfriend.
When McGurn’s men thought they saw Bugs Moran, they got into their police uniforms and drove over to the garage in a stolen police car. The bootleggers, caught in the act, lined up against the wall. McGurn’s men took the bootleggers' guns and opened fire with two machine guns. All the men except Frank Gusenberg were killed outright in cold blood.
The plan appeared to go brilliantly except for one major detail; Bugs Moran was not among the dead. Moran had seen the police car and took off, not wanting to be caught up in the raid.
Even though Al Capone was conveniently in Florida, the police and the newspapers knew who had staged the massacre. The St. Valentine’s Day Massacre became a national media event immortalising Capone as the most ruthless, feared, smartest and elegant of gangland bosses.
Even while powerful forces were amassing against him, Capone indulged in one last bloody act of revenge – the killing of two Sicilian colleagues who he believed had betrayed him. Capone invited his victims to a sumptuous banquet where he brutally pulverised them with a baseball bat. Capone had observed the old tradition of wining and dining traitors before executing them.