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Crime Throughout History: Saint Valentine’s Day Massacre

Criminal Law Blog by The Law Office of Greg Tsioros

Crime Throughout History: Saint Valentine’s Day Massacre

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Note: This is a new series for the blog that will be featured once per month, Crime Throughout History. With each post we will focus on an infamous crime and explore the details surrounding it. We’re kicking off this feature with one of America’s most well-known crimes: The Saint Valentine’s Day Massacre.

When people talk about the history of organized crime in the United States, they may mention the Mafia, bootlegging and bloody shootouts in back alleys. Although many of these events have been glamorized in Hollywood films, the early 20th century in America was heavily impacted by the effects of organized crime. One of the most infamous incidents of the gangster area is known as the Saint Valentine’s Day Massacre.

This violent mass murder has achieved legendary status because it involved some of the most notorious gangsters of the era. It marked a turning point in the war on gang violence and it ushered in the decline of major Mafia-style gang activity in Chicago.

The Crime

On February 14, 1929, in Chicago’s Lincoln Park neighborhood, seven men who were associated with the Irish North Side Gang were shot to death in a planned, organized attack. The massacre likely took place as a result of fierce competition between Bugs Moran’s North Side Gang and Al Capone’s Italian South Side Gang.

The two mobsters had been struggling to control the local criminal rackets in the city. At the time, Prohibition was being enforced, giving organized criminals a chance to increase their illegal profits. The biggest rackets in the city included:

  • Bootlegging alcohol
  • Prostitution
  • Gambling

The two gangs had carried out assassinations against high-ranking members of opposing organizations in the years leading up to the massacre. The massacre likely took place in an attempt to take out the leadership of the Irish North Side Gang.

On the day of the massacre, seven North Side Gang members met in a garage at 2122 North Clark Street. It is likely that they were lured there with the promise of a shipment of bootleg whiskey. Two men dressed in police uniforms and two men in plain clothes drove up to and entered the garage and lined up the North Side members against a wall.

They opened fire with two Thompson submachine guns and two shotguns, killing or fatally wounding all seven gangsters. The shooters dressed as police officers then led the two other shooters out of the garage at gunpoint to give the appearance that they were arresting the men. The four then drove away. They have never been identified.

The Investigation

Several witnesses were interviewed after the massacre but no positive identifications were made. Although the identities of the shooters are not known, it is extremely likely that they were members of the Italian South Side Gang. It is even possible that the shooting was planned, ordered and organized by Al Capone himself.

In January of 1935, a small-time criminal named Byron Bolton was arrested in a police raid in Chicago. While being interrogated, he delivered a large amount of information to the police, including some information about the location of other criminals that turned out to be reliable. He also freely claimed to have acted as a lookout in the Saint Valentine’s Day Massacre and he named the alleged shooters and others involved in the crime.

Bolton also claimed that Capone and several other high-ranking Mafia members planned the shooting in advance. Despite these claims, the investigation proved to be difficult. Most of the criminals alleged to be responsible for the shooting were dead by the time of Bolton’s statements. Further interrogations turned up little useful information and the shooters were never positively identified.

The Aftermath

Ironically, the massacre effectively gave Capone’s gang control of the Chicago rackets but it also led to his eventual arrest. With no serious competition, Capone became the most notorious gangster in the nation and he was named Public Enemy Number One. The murders also caused Capone to lose favor and respect with the public as they made him seem violent and ruthless.

One month after the massacre, in March 1929, Capone was arrested for contempt of court after failing to appear to testify for a summons. Over the next two years, Capone was repeatedly arrested and imprisoned as federal investigators searched for evidence related to his income and tax payments.

In 1931, Capone was indicted and eventually found guilty of income tax invasion and was sentenced to 11 years in prison. After his release, he lived out the rest of his life in isolation, having become severely ill from the effects of untreated syphilis.

The Saint Valentine’s Day Massacre still stands as one of the most violent gangster crimes in the history of the United States. The resulting fallout set a new precedent for investigating organized crime and led to the downfall of the most infamous gangster in the country. Although the massacre was violent and bloody, it forever changed the way that law enforcement fights crime in America.

This infamous crime in history is brought to you by The Law Office of Greg Tsioros. If you are in need of experienced legal representation, contact his office today at (832) 752-5972.

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