The Life of Al Capone

Podcast Transcript

Alphonse Gabriel Capone, aka Al Capone, aka Scarface, is one of the most notorious gangsters in American history.

Known for dominating Chicago’s underworld during Prohibition, he gained fame and notoriety throughout the United States.

Capone cultivated a celebrity image while participating in violent criminal activity. Despite his wealth and fame, in the end, he wound up in prison and died an early death.

Learn about the life and criminal exploits of Al Capone on this episode of Everything Everywhere Daily.

Alphonse Gabriel Capone was born in Brooklyn, New York, to Italian immigrant parents on January 17, 1899. He was one of nine children and spent much of his childhood working odd jobs.

Capone was considered a promising student as a child. However, he struggled to follow the rules in a strict Catholic School. He was eventually kicked out for hitting a teacher in the face.

In his youth, Capone actively participated in New York’s Five Points Gang. This gang mainly included younger Italian Americans and helped launch several of America’s most prominent gangsters.

During his time with the Five Points Gang, Capone met Johnny Torrio.

Torrio masterminded many of the Five Point Gang’s operations, overseeing drug trafficking, prostitution, and loan-sharking.

After meeting Capone, Torrio recognized his potential in organized crime and mentored him. Even after Torrio moved to Chicago in 1909, they maintained their connection. It was Torrio who taught Capone everything he knew about organized crime.

Capone mostly stayed out of trouble until 1917, when Torrio helped him get a job under gangster Frankie Yale.

Yale hired Capone as a bartender and bouncer at the Harvard Inn in Brooklyn. During one shift, Capone insulted a woman. Her brother retaliated, leaving Capone with a massive, superficial facial scar. It was this incident that earned him the nickname ‘Scarface.’

In December 1918, at the age of 19, Capone married Mae Josephine Coughlin. Their son, Albert Francis Capone, was born the month before. Capone named Torrio the godfather.

Although Capone still had illegal connections, he reportedly wanted to provide for his family honestly. Capone moved Mae and Albert to Baltimore and worked as a bookkeeper for a construction company.

Capone held this position for only about a year, until 1920, when two key events occurred: his father’s death and Torrio’s invitation for Capone and his family to move to Chicago, an opportunity Capone jumped at.

In Chicago, Capone worked as an enforcer for crime boss James ‘Big Jim’ Colosimo. Enforcers mainly ensure that rules are followed, debts are collected, and threats are addressed. Capone started as a bouncer at a one of Big Jim’s brothels.

Just before Capone arrived in Chicago, the government passed the 18th Amendment, which banned the sale of alcohol and ushered in the era of Prohibition, which in turn created a lucrative black market for alcohol sales.

Big Jim reportedly refused to join the bootlegging business, choosing instead to focus on gambling and brothels. Many people suspect Torrio ordered Big Jim’s murder as a result.

‘Big Jim’ Colosimo was killed by a gunman at a cafe on May 11, 1920. The assassin was allegedly none other than Frankie Yale, who was brought in from New York to do the hit.

With Big Jim gone, Torrio took over his gang, which became known as ‘the Outfit.’ He quickly expanded into bootlegging. Torrio’s leadership was brief; after a rival gang shot and injured him in 1925, police arrested him for operating a distillery.

Torrio’s departure left Capone as the new leader of the gang.

Capone immediately made himself a public figure, disregarding his mentors’ advice. He moved the gang’s base into the heart of Chicago and lived lavishly in the public eye. As the leader of ‘The Outfit,’ Capone became the most visible mobster in the United States.

Capone wore custom suits and flashy jewelry. He drank gourmet beverages, dined on fine food, and smoked fancy cigars, making himself a celebrity across the country.

He regularly appeared in local media and collaborated with politicians to cultivate his public persona. Capone projected the image of a generous businessman who cared for Chicago’s residents, not a violent mobster. Many saw him as a ‘Robinhood’ figure, especially by those who resented prohibition.

Capone maintained strong ties with local politicians and law enforcement during a time of escalating gang warfare. These connections enabled him to expand his criminal empire and make bold, calculated moves through violence.

Capone’s primary revenue sources were bootlegging, prostitution, and gambling.

To bring alcohol into Chicago, Capone partnered with Canadian bootleggers. Despite denying these ties, he worked with Rocco Perri, known as the ‘King of Canadian Bootleggers.’ Capone used transportation networks and illegal distilleries to keep Chicago supplied with alcohol.

To make sure customers were buying alcohol from him, Capone employed a policy of blowing up the establishments of anyone who purchased booze from his competitors. This helped ensure establishments would only buy alcohol from him. An estimated 100 people died from these bombings.

However, business was not completely smooth sailing.

The Outfit was not the only gang in Chicago, and Capone had plenty of enemies.

When Capone moved to a home in Cicero, Illinois, he protected his property using threats of violence and bribery to ensure his safety in the area.

In April 1926, Capone ordered his men to gun down some North Siders spotted in Cicero. Unbeknownst to him, public prosecutor William McSwiggin was among them. McSwiggin died in the shooting, drawing more public scrutiny to the lawlessness of Chicago.

The public demanded justice, prompting police to search Capone’s home for murder evidence. While they found nothing, they did collect financial documents that would become relevant later on.

Violence in Chicago escalated further when the Northsiders tried to kill Capone in September that year.

Hitmen lured Capone to the windows at his headquarters and shot at him with shotguns and submachine guns. Though unharmed, Capone responded to public pressure and the attempt on his life by calling for a gang truce. The peace lasted only two months before violence resumed.

During the period between 1926 and 1929, Capone operated in a similar manner to his early years as a mob boss.

He maintained a public-facing role, led through violence, and expanded his criminal empire. There were numerous incidents of violence, corruption, and criminal activity during this period, which are far too numerous to list here.

The most notorious act of violence during this period was the St. Valentine’s Massacre, which I covered in detail in a previous episode.

The St Valentine’s Massacre is widely assumed to have been ordered by Capone, but his alibi is that he was in Florida when it occurred.

This event saw Capone target one of his longtime rivals, “Bugs” Moran. Moran was the head of Chicago’s North Side Gang and one of the main figures preventing Capone from achieving complete domination of the Chicago bootlegging business.

Moran had ordered hits on Capone, Torrio, and other top members of ‘The Outfit.’ In 1929, Moran ordered a hit on Capone’s top man, “Machine Gun” Jack McGurn. It is believed that McGurn and Capone plotted to kill Moran in retaliation.

On February 14, 1929, Capone’s men rented an apartment near Moran’s Headquarters. Lookouts gave a signal to armed men dressed as police officers to begin a fake raid of the establishment.

Capone’s men entered Moran’s headquarters dressed as cops. They lined seven men along the wall and shot them in cold blood. Moran was not among the victims.

The shocking images from the massacre disgusted the public. Authorities tried to bring Capone in to testify, but he claimed illness. Capone then tried to improve his image by donating to charities and sponsoring soup kitchens.

Despite his efforts to improve his image, Capone was widely blamed and labeled a public enemy by the media.

Federal pressure on Capone intensified.

The public outcry from the St Valentine’s Massacre led to President Herbert Hoover becoming directly involved in solving Chicago’s crime problem.

Hoover ordered federal agencies, including the Prohibition Bureau, the Treasury and Justice Departments, to target Capone.

The first arrest came on March 27, 1929. The FBI arrested him for contempt of court for faking an illness to avoid an earlier court appearance. He was arrested again in Philadelphia on May 17, 1929, for carrying a concealed weapon. Capone pleaded guilty to carrying a weapon and was sentenced to prison for a year, though he only served nine months for good behavior.

Capone was released in March of 1930, but was arrested again in April in Miami, Florida. This time, he was charged with vagrancy charges, which essentially means being charged for being homeless and participating in behaviors like loitering.

After this arrest, Capone claimed that Miami’s police threatened to arrest his family and refused to give him food and water. These claims led Miami police to charge him with perjury.

He was later acquitted of all charges.

Capone continued to be pulled into court case after court case until he was ultimately defeated by the IRS.

In 1927, the United States v. Sullivan case held that illegally earned income was still subject to income tax. This ruling gave the government a way to tax wealthy criminal figures for tax evasion, given the luxurious lifestyles they led.

Capone obviously had income he was not declaring on his taxes, as evidenced by his lifestyle, allowing the prosecution to develop a pretty slam-dunk case against the mobster.

Capone attempted to avoid this charge by drafting a letter with his attorney outlining the amount he owed the IRS and stating that he was willing to pay taxes for previous years.

However, this backfired horribly, as the IRS now had a letter of how much Capone owed them without needing to fully investigate. He essentially handed over a confession to committing tax evasion.

Capone was indicted on twenty-two counts of income tax evasion and 5,000 violations of the Volstead Act for trafficking alcohol.

Capone was convicted of five counts of tax evasion and sentenced to 11 years in federal prison, fined thousands of dollars, and held liable for hundreds of thousands more.

Capone was first sent to the Atlanta Federal Penitentiary in 1932 and was moved to Alcatraz in 1934.

Capone’s time in Alcatraz wasn’t great. He was stabbed by a fellow inmate and began to mentally decline from neurosyphilis, which completely eroded his mental faculties. During his final year in prison, he was reportedly disoriented and confused, spending most of his time in the prison hospital.

Capone was moved from Alcatraz to the Federal Correctional Institution at Terminal Island in Los Angeles in January of 1939. In November of the same year, he was paroled because of his reduced mental capabilities.

Putting Al Capone behind bars did not solve Chicago’s gang problems. Despite Capone’s arrest being portrayed as undermining organized crime, the reality of the situation was that ‘the Outfit’ and other gangs were still functioning, just with less visible violence.

As for Capone, he spent the rest of his life battling syphilitic paresis, which is essentially dementia caused by syphilis. He suffered from the illness until his death on January 25, 1947.

Despite his death, Al Capone’s legacy as a notorious mobster has lived on. He has become the subject of multiple books and movies.

The 1983 movie Scarface, starring Al Pacino, is actually a remake of the 1932 movie Scarface starring James Cagney, which was based on Al Capone.

In the 1987 film The Untouchables, Al Capone is portrayed by Robert De Niro.

Al Capone has become a larger-than-life figure. Hero to some and villain to others. There are dozens of Al Capone-related historic sites around the country related to places that he visited.

Even almost 80 years after his death, he is still one of the most notorious mobsters in American history.

The Executive Producer of Everything Everywhere Daily is Charles Daniel. The Associate Producers are Austin Oetken and Cameron Kieffer.

Research and writing for this episode were provided by THE… Olivia Ashe.

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