Al Capone, Baby Face Nelson, Machine Gun Kelly, and John Dillinger… the notorious names conjure up Goodfellas, robberies, and jailbreaks.
‘Scarface’ Al Capone was in a brutal mobster class of his own, however. Born in Brooklyn in 1899, Capone quit school after the sixth grade and joined a street gang led by Johnny ‘The Fox’ Torrio. Lucky Luciano was among the members.
The Roaring Twenties and America’s Prohibition Amendment created a boom time for gangsters. Capone joined Torrio in Chicago where he’d become an influential lieutenant in ‘Big Jim’ Colosimo’s mob. The rackets spawned by the Prohibition Amendment included illegal brewing, distilling and distribution of beer and liquor - ‘growth industries’ for Goodfellas.
Torri and Capone also developed legit businesses in the cleaning and dyeing fields; it helped them cultivate influence with labor unions and public officials.
Big Jim Colosimo was gunned down; no one was ever charged
The Rise of Scarface
With the violent death of Big Jim Colosimo, Torrio became the leader with Capone as his strong right arm but - perhaps to no one’s surprise but Torrio’s - The Fox was shot five times outside his home and left for dead by George ‘Bugs’ Moran and Earl J. ‘Hymie’ Weiss, leader of the rival North Side gang. While Torrio survived, he was seriously injured and passed the torch to ‘Scarface’ Capone.
Capone, now the godfather, dominated a shadowy empire of Chicago crime, extending his reign across gambling, prostitution, bootlegging, bribery, narcotics trafficking, robbery, protection rackets, and murder. Moran mockingly referred to him as ‘The Beast’. The intriguing twist lay in the seemingly impervious shield that protected Capone from the grasp of law enforcement, leaving a windy city held captive by the enigmatic underworld figure.
The FBI had limited jurisdiction in the 1920s and ‘30s, unable to delve into gang warfare. It was a matter for the state of Illinois. The Bureau needed a federal crime and evidence to back up a case. Eventually, that day would come, but not the way many people envisioned.
This story is part of our weekly briefing. Sign up to receive the FREE briefing to your inbox.
Al Capone, Baby Face Nelson, Machine Gun Kelly, and John Dillinger… the notorious names conjure up Goodfellas, robberies, and jailbreaks.
‘Scarface’ Al Capone was in a brutal mobster class of his own, however. Born in Brooklyn in 1899, Capone quit school after the sixth grade and joined a street gang led by Johnny ‘The Fox’ Torrio. Lucky Luciano was among the members.
The Roaring Twenties and America’s Prohibition Amendment created a boom time for gangsters. Capone joined Torrio in Chicago where he’d become an influential lieutenant in ‘Big Jim’ Colosimo’s mob. The rackets spawned by the Prohibition Amendment included illegal brewing, distilling and distribution of beer and liquor - ‘growth industries’ for Goodfellas.
Torri and Capone also developed legit businesses in the cleaning and dyeing fields; it helped them cultivate influence with labor unions and public officials.
Big Jim Colosimo was gunned down; no one was ever charged
The Rise of Scarface
With the violent death of Big Jim Colosimo, Torrio became the leader with Capone as his strong right arm but - perhaps to no one’s surprise but Torrio’s - The Fox was shot five times outside his home and left for dead by George ‘Bugs’ Moran and Earl J. ‘Hymie’ Weiss, leader of the rival North Side gang. While Torrio survived, he was seriously injured and passed the torch to ‘Scarface’ Capone.
Capone, now the godfather, dominated a shadowy empire of Chicago crime, extending his reign across gambling, prostitution, bootlegging, bribery, narcotics trafficking, robbery, protection rackets, and murder. Moran mockingly referred to him as ‘The Beast’. The intriguing twist lay in the seemingly impervious shield that protected Capone from the grasp of law enforcement, leaving a windy city held captive by the enigmatic underworld figure.
The FBI had limited jurisdiction in the 1920s and ‘30s, unable to delve into gang warfare. It was a matter for the state of Illinois. The Bureau needed a federal crime and evidence to back up a case. Eventually, that day would come, but not the way many people envisioned.
February 14, 1929. The infamous St. Valentine's Day Massacre unfolded in a grimy garage at 2122 North Clark Street in Chicago, the HQ for Bugs Moran’s gang. Two of the four assailants were dressed as uniformed police officers and talked their way inside. They lined up seven of Moran's crew against the wall and brutally murdered them with unrelenting machine-gun fire.
Witnesses recalled the four men sped off in a black Cadillac touring car complete with a police siren. The murdered crew had been awaiting delivery of high-grade hooch that fatal morning. Coincidentally, Bugs Moran was late for work and dodged his fate. Before the massacre, police officers had been stealing bootleg liquor from the gang's trucks but there was no evidence they were involved in the murders. The coincidences raised questions and eyebrows, however. Was it a police job? A set-up? Was Moran tipped off? While the massacre was attributed to Capone and his mob, intriguingly, Scarface was in Florida.
The echoing gunshots defined the power struggle between Scarface’s gang and Moran's North Side Irish mob, along with the Chicago police force’s curious inability to do anything about it. Despite investigations and hearings, no one was ever charged with the Valentine's Day Massacre and Chicagoans despaired. “The butchering of seven men [in] open daylight raises this question for Chicago: Is it helpless?” the Tribune editorialized.
The audacious brutality cast Capone as ‘Public Enemy Number One’ despite his alibi. Scarface appeared to be untouchable until March 1929 when Capone dodged a federal grand jury appearance citing bronchial pneumonia. The FBI found inconsistencies in his excuse, however. Witnesses saw Capone at the race tracks in Miami and on a cruise to Nassau. He didn’t seem to be ill.
Tracking Al Capone
If the Feds couldn’t arrest Capone for murder, they could at least make his life miserable. In 1929, Capone was charged with contempt of court. He was then arrested in Philadelphia on a concealed weapons charge.
Simultaneously, the US Treasury pursued tax evasion charges against Capone, his brother, and other mobsters. With only two things certain in life - death and taxes - Capone decided to plead guilty in 1931, expecting a lenient sentence but receiving 11 years in federal prison, a $50,000 fine, and back taxes. After failed appeals, Capone served his time in Atlanta and Alcatraz.
Was he behind the St. Valentine’s Day massacre, one of the most infamous gangland slayings in American history? Scarface was never convicted of the killings. He was released from Alcatraz in 1939 after almost eight years in prison. His health was already failing and he died of a stroke and pneumonia in 1947 at his Florida home. Capone never returned to Illinois again. His rival, Bugs Moran, died of lung cancer a decade later at the age of 63, a few months into a 10-year sentence at Leavenworth Federal Prison in Kansas.
In the twilight of Prohibition-era crime, the massacre remains a haunting tableau, blending mystery, brutality, and the unraveling of Chicago's underworld.
This story is part of our weekly briefing. Sign up to receive the FREE briefing to your inbox.
Gadgets & Gifts
Put your spy skills to work with these fabulous choices from secret notepads & invisible inks to Hacker hoodies & high-tech handbags. We also have an exceptional range of rare spy books, including many signed first editions.
We all have valuable spy skills - your mission is to discover yours. See if you have what it takes to be a secret agent, with our authentic spy skills evaluation* developed by a former Head of Training at British Intelligence. It's FREE so share & compare with friends now!
