Chicago Crime: The Story of Al Capone

How gangsters ran an underground city of vice in the 1920s.

For Chicago, the year 1920 was the beginning of massive change. Prohibition laws were passed, making it illegal to buy or sell alcohol. Overnight, ordinary people became criminals. Gangsters emerged as folk heroes. Men like Al Capone found a new way of getting rich quick. Capone came from New York to Chicago in search of bootlegging fortunes. The city’s illegal liquor trade was run by amateurs, and he hoped to seize control of it. 

City of vice

Chicago was the perfect place for vice to flourish. The heart of commerce, it was a highly accessible location. Lakes, rivers, and railroads provided numerous ways to reach the city. The city already had its own vice district, known as the Levee. Located on the South Side of Chicago, most of the city’s illegal activity was concentrated in that single district. Many local authorities across America begrudgingly recognized the need for such districts, which served as a way of quarantining the illicit activity. Capone started out at Colosimo’s, where he supplied liquor and ran protection rackets. Because he owned all the alcohol, Capone acquired control over the district’s bars. Gradually, the crime boss expanded his underground enterprise to include gambling and prostitution. Prostitutes operated out of the nearby Cullerton Hotel. But in sharp contrast to the glamor of Capone’s image, these brothels were tiny and cramped. Each bedroom was no bigger than a prison cell. 

Green Mill Bar

Capone kept his physical distance from his shady operations on the South Side. Instead, he catered to upper-class clientele from his Green Mill Bar on the North Side. Capone’s syndicate seized control of the place in the 1920s. This fancy bar served alcohol to the city’s rich and powerful. It had a formal atmosphere, where women wore gloves and hats. Men had to be dressed in a suit just to get in. The bar’s booze was smuggled by Capone, or produced by his breweries. If sales were low, the owner would be threatened by Capone’s henchmen. Capone’s gangsterism made him many enemies, and he lived in constant fear of retaliation. Because of this, the bar was outfitted with a hidden escape route. Both literally and figuratively, Chicago had a criminal underworld. Tunnels stretched underground for miles, sometimes feeding into other bars and establishments above ground. The tunnels were used for smuggling booze into cellars, and to make daring escapes from law enforcement. Under Capone’s leadership, the Chicago bootlegging industry went from an amateur activity into a big business. Money purchased him influence, allowing the crime boss to pay off the city’s officials. Mayor Bill Thompson was willing to turn a blind eye to Chicago’s speakeasies. But the situation changed in 1923, when Thompson was voted out of office. He was replaced by William Dever, a man on a mission to enforce the Prohibition laws. After three years in the booze business, Capone’s empire faced the growing threat of zealous public officials, who cracked down fiercely on the illegal sale of liquor. Capone moved his family out of the ganglands, relocating to a modest home in South Chicago for $5,500. It was purchased in his wife’s name. There, he hid the large stacks of money he made from his underground activities. Capone’s getaway house was small and intimate. He met with henchmen in the tiny Blue Room. His own bedroom was not much bigger. A tender family man, he provided a comfortable existence for his wife and children. But he also purchased another apartment on the South Side, where he caroused and partied with his nighttime mistresses. Capone was ever the womanizer, and syphilis would later be his cause of death. His private parties were full of alcohol and cocaine. 

Hawthorne Hotel

As Mayor Dever cracked down on booze, Capone’s underground business was forced to expand into the city’s suburbs. He went to Cicero, five miles from downtown. Capone transformed Cicero from a quiet suburb into the biggest gambling hotspot west of Atlantic City. Cicero was the perfect place for Capone, who knew its corrupt officials could easily be purchased. It became a marriage of convenience between organized crime and party politics. Refusing to hide from the law, Capone was determined to rise above it. When town elections were held in 1924, Capone’s men unleashed a reign of terror. Voters were threatened and harassed with beatings. Capone’s henchmen reportedly stood in poll booths with their guns drawn. Gunfire erupted on the streets outside of polling locations. Capone’s methods were effective, and he successfully subdued the town under his tyrannical control. Having entrenched himself in Cicero, it became a base of operations for Capone’s further expansion. Hawthorne Hotel became the center of Capone’s illicit activity, located on Cicero’s Main Street. It was home to a bar, a brothel, and a gambling joint. Out of Hawthorne, the gangster covertly operated 250 other buildings. He established a race track, where he enjoyed betting on horses. Capone continued to generate massive profits, fearing only the intrusion of other gangs. He narrowly survived an assassination attempt outside Hawthorne in 1926. 

Metropole Hotel

Although Capone’s crime empire enjoyed explosive growth, so did the rest of Chicago. Skyscrapers were erected, creating the city’s modern skyline. No longer interested in suburban crime, Capone hoped to venture into the legitimate business operations of downtown Chicago. Skyscrapers emerged as an enduring symbol of American commercialism and entrepreneurial success. These buildings were constructed using cassions, which connected them into limestone rock foundations. The introduction of steel frames in the 1920s allowed buildings to become taller without increasingly their weight too much. Structures became lighter and taller, but were vulnerable to strong winds. To handle this issue, special beams were added to stabilize the skyscrapers. The Chicago Board of Trade was proposed to become the tallest building west of New York City. It became a symbol of Chicago’s new merchant elites, who flaunted their wealth by constructing monuments of commerce. Clad with limestone, the building’s 43 stories stood at 609 feet. Atop the building was a statue of the Roman goddess Ceres, who symbolized agriculture and trade. The Board of Trade was completed in 1929, and remained Chicago’s tallest building until 1965. In 1928, Capone paid $250,000 to ensure the loyalty of the city’s mayor. He moved out of Cicero, setting up headquarters at the downtown Metropole Hotel. From this site, the crime boss operated 50 hotel suites. Now operating out of central Chicago, the crime kingpin was no longer a shadowy figure. He was now a visible figure in Chicago’s public life. Public authorities tolerated his presence, as long as his criminal activities were kept out of sight. But eventually, gang violence spread to the central city. 

Saint Valentine’s Day Massacre

By early 1929, Capone had reestablished himself in downtown Chicago, where he supplied illegal liquor across the city. Tensions grew as Capone’s empire faced challenges from a rival gang. Led by Bugs Moran, they were known as the North Side Gang. Moran’s men challenged Capone and his empire, which dominated the South Side. This rivalry resulted in one of the worst massacres in the history of organized crime. Known as the Saint Valentine’s Day Massacre, it became the legendary subject of countless Hollywood movies over the years. The crime was perpetrated at the Clark Street Garage, one of the North Side Gang hangouts. Two of Capone’s men slipped into the garage, disguised as police officers. They pretended they were raiding the North Side Gang. Another two armed henchmen came in from the front door along Clark Street. Moran’s men surrendered their weapons to the phony cops. As they raised their hands and stood up against the wall, the North Side Gang was fired upon by Capone’s assassins. The weapon of choice was the Thompson submachine gun, commonly called the Tommy gun. First produced in 1920, Tommy guns were so common in Chicago, that they were nicknamed the Chicago typewriter. The Tommy gun is a recoil-operated fully automatic weapon. When loaded and cocked, the spring bounces as the gun unloads a fast flurry of lead bullets. A fully loaded Tommy gun can weigh up to 20 pounds. It fires at a rate of 800 rounds per minute. An estimated 90 rounds were fired by Capone’s men at the seven North Side gangsters. Capone himself managed to evade justice, because his culpability in the crime was too difficult to prove. But Capone underestimated the damage it would do to his public reputation. The Saint Valentine’s Day Massacre became an unsightly symbol of Chicago’s crime and lawlessness. The public grew increasingly outraged and agitated by the presence of organized crime in their city. Capone was declared public enemy number one. 

Downfall

In the face of public pressure, the federal government managed to secure a conviction of Capone on charges of tax evasion. The crime boss was convicted in October of 1931, and sentenced to elven years in a federal penitentiary. After filing an appeal, he was taken to the Cook County Jail to await his fate. The jail was one of the most high-security facilities in America. It was where Capone spent his last days in Chicago. Cook County Jail was originally constructed to hold 3,200 inmates. Today, it holds nearly 9,000. It was built to be the most modern facility of its kind. The cells are tiny, just five by eight feet. Each has two beds. Most inmates are denied even the most basic luxuries. But when Capone was in jail, he managed to leverage his outside connections to gain special favors. He gained access to a block of cells, and was permitted to host special guests. This allowed Capone to operate his criminal enterprise while still in prison. Capone had thought his time in jail would be short-lived. Little did he realize, his racketeering days were over. After spending six months at Cook County, Capone spent seven years at various penitentiaries. Capone was released from Cook County in 1932, and boarded a train out of Chicago. His criminal empire had reached its end. The next year, Prohibition was repealed. It became a death knell to the illicit enterprises of the liquor-trafficking gangs. The gangster was sent to Alcatraz, where he finished his sentence in 1939. By this time, his physical and mental health had irreparably deteriorated. He died in Florida eight years later. The cause of death was a heart attack, probably a complication of syphilis. He was only 48 years old. In a span of twelve years, Capone oversaw one of the most notorious and lucrative criminal enterprises of Chicago’s underworld. But the tunnels, hotels, lots, and prisons of the Capone Era continue to be iconic landmarks of Chicago’s history.

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