Your guide to the Prohibition-era gangster Al Capone

What was Al Capone’s childhood like?

The son of a barber and a seamstress, there was nothing in Alphonse Capone’s childhood that suggested he would fall into a life of crime. However, having started out as a diligent student, he began to fall behind with his schoolwork and left school at the age of 14 after assaulting his teacher.

Capone belonged to two New York street gangs as a boy and worked a number of odd jobs, including as a bowling alley pinboy and candy store clerk. As a member of a gang known as the James Street Boys, Capone struck up a friendship with its leader, Johnny Torrio, who would become his lifelong mentor.

Capone joined the Five Points Gang in Manhattan at the age of 16. He took up work as a bouncer and bartender at the Harvard Inn, a cheap bar and brothel off New York’s Coney Island boardwalk, that was owned by the mobster Frankie Yale. Yale, who was one of Brooklyn’s biggest bootleggers during the Prohibition era, took Capone under his wing.

• Listen | Timothy Hickman answers listener questions about the ban on booze in 1920s America, from speakeasies and moonshine to Al Capone’s shady dealings

How did Al Capone get the nickname ‘Scarface’?

In 1917, while working at the Harvard Inn, Al Capone had his left cheek slashed by a man named Frank Galluccio, whose sister, Lena, Capone had reportedly insulted with a crude comment. Galluccio slashed Capone’s cheek three times using a penknife, leaving a trio of deep cuts which would require 30 stitches. Intensely self-conscious about his scars, Capone tried to hide them in photographs and often told people he sustained them while fighting with the “lost battalion” in France during the First World War (although in reality he never fought in combat).

Capone was dubbed ‘Scarface’ by the press when he rose to fame, but he despised the nickname. In 1932, the actor Paul Muni played a gangster loosely based on Capone in the film Scarface: The Shame of a Nation. The film was considered so amoral when it was released that it was banned in several parts of the United States. Capone reputedly obtained a copy of the film for private screenings.

How did Capone become a Chicago mob boss?

In 1918, at the age of 19, Al Capone married Mae Coughlin, who had recently given birth to their son, Albert Francis. Wanting to do right by his family and make an honest living, Capone moved them to Baltimore, Maryland, where he began working as a bookkeeper for a construction company. But an offer from his childhood mentor Johnny Torrio to join him as a member of the Colosimo mob in Chicago, which Torrio had recently taken charge of, proved impossible to resist, and in 1920 Capone joined the operation. He relocated his wife and son, along with his mother and several of his siblings, to the city shortly afterwards.

The Colosimo mob was a Prohibition-era gang that made its money in the illegal brewing, distilling and distribution of beer and liquor. The 18th Amendment to the constitution prohibiting the manufacture, sale or transportation of alcohol had been ratified in 1919 and enforced from January 1920.

• Read more about the impact of Prohibition

Torrio became head of the gang following the brutal murder of its founder, Big Jim Colosimo, in May 1920. Colosimo was gunned down in his restaurant on 11 May 1920 in an attack rumoured to have been orchestrated by Torrio himself.

In 1925, Torrio decided to flee the country and return to Italy following an attempt on his life. Just five years after joining the Colosimo mob, the 26-year-old Al Capone took charge of the operation. He quickly set to work expanding the Chicago outfit and building upon his fearsome reputation – newspapers at the time estimated his operations generated $100m in revenue annually, primarily from bootlegging, gambling, prostitution, and racketeering. Soon, Capone’s gang dominated the city.

What was the Valentine’s Day Massacre?

On 14 February 1929, seven members of the rival George “Bugs” Moran mob were machine-gunned to death while lined up against a garage wall in Chicago’s Lincoln Park neighbourhood. At least two of the gunmen were posing as police officers. The massacre was ascribed to Capone’s mob, although he himself was in Florida at the time.

The incident shocked and appalled the nation, but the case remained unsolved, and Capone was never charged.

• Quiz | Prohibition: how much do you know about the US ban on booze?

What crimes did Al Capone commit? How did he end up in prison?

Somewhat surprisingly, the 1929 Valentine’s Day Massacre killings were not a federal offence at the time and so were not within the Federal Bureau of Investigation’s remit.

In fact, Al Capone was never convicted of murder. The FBI’s official interest in him began with a much more innocuous offence: just weeks after the Valentine’s Day Massacre, on 27 February 1929, Capone was subpoenaed at his winter home near Miami, Florida, to appear as a witness before a federal grand jury in Chicago on 12 March for a case involving a violation of prohibition laws. The day before he was due to appear before the jury, on 11 March, Capone’s lawyers filed for postponement of his appearance on the basis that he was bedridden with bronchial pneumonia in Miami.

His appearance date was re-set for 20 March, but it soon transpired that Capone had been lying about his supposed illness. On request of the US Attorney’s Office, FBI agents obtained statements that showed Capone had attended racetracks in Miami, made a plane trip to Bimini in the Bahamas, and even enjoyed a cruise to Nassau.

Capone appeared before the federal grand jury in Chicago as planned on 20 March 1929 and completed his testimony on 27 March. But as he left the courtroom, he was arrested by FBI agents for contempt of court – an offence which carried one year in prison. “He was released on bond, but from there on, it was downhill for the notorious gangster,” said the FBI in a 2005 article on Al Capone’s demise.

Capone was convicted of multiple crimes from 1929 onwards – first, in May 1929, he was arrested along with his bodyguard in Philadelphia by local police for carrying concealed weapons and served nine months in jail. Then, in February 1931, he was found guilty in federal court on the aforementioned contempt of court charge and was sentenced to six months in Cook County Jail in Chicago.

But the nail in Capone’s coffin came on 18 October 1931, when he was convicted after a trial of tax evasion. On 24 October, Capone was sentenced to 11 years in federal prison. He was held in Cook County while awaiting the results of his appeals, but after they were denied he was sent to the US Penitentiary in Atlanta, serving his sentence there and at the recently opened federal penitentiary on Alcatraz Island in San Francisco Bay.

Capone was also fined $50,000 and charged $7,692 for court costs, in addition to $215,000 plus interest due on back taxes. The six-month contempt of court sentence was to be served concurrently.

When was Al Capone released from prison?

Al Capone’s health deteriorated significantly while he was in jail – in 1938 he was diagnosed with neurosyphilis, an infection of the central nervous system caused by the sexually transmitted infection syphilis, which was not yet easily treatable. He spent the remainder of his sentence in Alcatraz’s hospital wing, with neurosyphilis eroding his mental faculties to the extent that he became certifiably insane. His wife’s appeal for parole was granted in 1939, on the grounds of good behaviour and on account of his medical condition.

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Al Capone was released from jail on 16 November 1939, having served seven years, six months, and 15 days. “Immediately on release he entered a Baltimore hospital for brain treatment and then went on to his Florida home, an estate on Palm Island in Biscayne Bay near Miami, which he had purchased in 1928,” according to the FBI.

In 1942, Al Capone became one of the first Americans to receive the antibiotic penicillin as treatment for syphilis. But although it helped to slow the progression of the disease, it was too late to save him, as the damage to his brain was irreversible.

When did Al Capone die?

On 21 January, at his Florida estate, Capone suffered a stroke and then contracted pneumonia. He died on 25 January 1947 after suffering a further cardiac arrest. His physician and a Baltimore psychiatrist both concluded that Capone by the time of his death, the former gangster had the mentality of a 12-year-old child.