The rise of organized crime in Chicago began with the advent of Prohibition. The law that banned the sale and production of liquor went into effect in 1920 and vast fortunes began to be made by lawless elements in the city. The decline of these criminal empires began almost a decade later in February 1929. It was on St. Valentine’s Day of that year that the general public no longer saw the mob as “public benefactors”, offering alcohol to a thirsty city, but as the collection of killers and thugs that it truly was.

Of course, the St. Valentine’s Day Massacre was not the death knell for the mob in Chicago. Organized crime remains in the city today, but it was this bloody event that changed the face of crime in Chicago forever. In the years that followed, empires crumbled and lives were destroyed, bringing an end to the “glory days” of the mob in Chicago.

During the 1920s, Al Capone worked his way up through the criminal ranks of Chicago’s South Side to virtually rule the city. His main competition was Dion O’Banion, the Irish gang leader of the North Side, who hampered every effort that Capone made to take over every section of the city. O’Banion was murdered in a flower shop that he owned near Holy Name Cathedral in November 1924 and after his death, the South Side mob murdered its way through every one who came to take his place, leaving only George “Bugs” Moran as the North Side’s last man standing.

On February 14, 1929, Capone decided that he wanted to have a very special “valentine” delivered to Moran. Through a contact, Capone arranged for someone to call Moran and tell him that a special shipment of hijacked whiskey was going to be delivered to one of Moran’s garages on the north side. Adam Heyer, a friend of Moran, owned the garage and it was used as a distribution point for North Side liquor. A sign out front read “S-M-C Cartage Co. Shipping - Packing - Long Distance Hauling”. It was located at 2122 North Clark Street.

On the morning of February 14, a group of Moran’s men gathered at the Clark Street garage. One of the men was Johnny May, an ex-safecracker who had been hired by Moran as an auto mechanic. He was working on a truck that morning, with his dog, a German Shepherd named Highball, tied to the bumper. In addition, six other men waited for the truck of hijacked whiskey to arrive. The men were Frank and Pete Gusenberg; James Clark, Moran's brother-in-law; Adam Heyer; Al Weinshank; and Reinhardt Schwimmer, a young optometrist who had befriended Moran and hung around the liquor warehouse just for the thrill of rubbing shoulders with gangsters.

Moran was already late for the morning meeting. He was due to arrive at 10:30 a.m. but didn't even leave for the rendezvous, in the company of Willie Marks and Ted Newberry, until several minutes after that. While the seven men waited inside of the warehouse, they had no idea that a police car had pulled up outside, or that Moran had spotted the car as he was driving south on Clark Street and rather than deal with what he believed was a shakedown, stopped at the next corner for a cup of coffee.

Five men got out of the police car, two of them in uniforms and three in civilian clothing. They entered the building and a few moments later, the clatter of machine gun fire broke the stillness of the snowy morning. Soon after, five figures emerged and they drove away. May's dog, inside of the warehouse, began barking and howling.

The landlady in the next building, Mrs. Jeanette Landesman, was bothered by the sound of the dog and she sent one of her boarders, C.L. McAllister, to the garage to see what was going on. He came outside two minutes later, his face a pale white color. He ran frantically up the stairs to beg Mrs. Landesman to call the police. He cried that the garage was full of dead men!

The police were quickly summoned and on entering the garage, were stunned by the carnage. Moran's men had been lined up against the rear wall of the garage and had been shot to death. Pete Gusenberg had died kneeling, slumped over a chair. James Clark had fallen on his face with half of his head blown away and Heyer, Schwimmer, Weinshank and May were thrown lifeless onto their backs. Only one of the men survived the slaughter and only for a few hours. Frank Gusenberg had crawled from the blood-sprayed wall where he had fallen and ended up out in the middle of the dirty floor. He was rushed to the Alexian Brothers Hospital, barely hanging on. Police sergeant Clarence Sweeney leaned down close to him and asked who had shot him. “No one --- nobody shot me,” he groaned and he died later that night.

The death toll of the massacre stood at seven but the killers had missed Moran. When the police contacted him later and asked who had sent the men to the garage, he “raved like a madman”. To the newspapers, Moran targeted Capone as ordering the hit. He proclaimed: “Only Capone kills guys like that.”

The St. Valentine’s Day Massacre broke the power of the North Side gang and marked the end of any significant gang opposition to Capone. However, it was also the event that finally began the decline of Capone’s criminal empire. He had just gone too far and the authorities, and even Capone's adoring public, were ready to put an end to the bootleg wars. The massacre started a wave of reform that would send Capone out of power for good.

In May 1929, Capone was summoned to New York to meet with Meyer Lansky and Charles “Lucky” Luciano, who were in the process of forming a national crime Syndicate. They were unhappy with the attention that Capone had attracted in Chicago and decided that it would be good public relations if Al Capone went to jail for a time. It was arranged for him to be arrested in Philadelphia on a charge of carrying a concealed weapon. Two detectives were paid $10,000 each to arrest him in the lobby of a movie theater, charge him and get him sentenced as quickly as possible. It all happened in just 16 hours and Capone was sentenced to spend a term of one year at the Eastern State Penitentiary.

Capone continued to conduct business from prison. He was given a private cell and allowed to make long-distance telephone calls from the warden’s office and to meet with his lawyers and with Frank Nitti, Jake Guzik and his brother, Ralph, all of whom made frequent trips to Philadelphia. He was released two months early on good behavior and when he returned to Chicago, he found himself branded Public Enemy Number One.

When Capone returned to Chicago in March 1930, he found the climate of the city had changed considerably during the time he had been away. His popularity had waned and the police were adamant about putting his operations out of business. Police Captain John Stege even posted a guard of 25 policemen in front of the Capone home on Prairie Avenue with orders to arrest him as soon as he arrived from Pennsylvania. Capone slipped quietly into the city, though, and took up residence at the Hawthorne Inn in Cicero, where he spent four days answering mail and getting caught up on the state of operations. Then, he and his attorneys blatantly called on Captain Stege and the United States District Attorney and found that neither of them had an actual warrant for his arrest. With that settled, he went home.