He was sometimes called “Scarface.” He was declared “Public Enemy No. 1” in 1930. And he was one of the most formidable and famous gangsters in American history. With a fedora tipped casually to the side, an elegant suit, and a cigar sometimes tucked between his teeth, Al Capone was the epitome of the organized-crime boss.
“Al Capone is the prototypical celebrity gangster,” historian Clarence Goodman told Chicago Stories. “He set the standard by which every other gangster who has his or her picture in the newspaper is judged.”
Although he eluded legal consequences for bootlegging and murder for years, Capone’s downfall would come in the form of something much more mundane: gambling ledgers.
Who Was Al Capone?
Before he became the infamous mobster, Capone had humble beginnings in New York. Alphonse Capone was born in Brooklyn to Italian immigrant parents and grew up in a traditional Catholic household. Diane Capone, who is the granddaughter of Al Capone, told Chicago Stories that he was the fourth oldest in the family and bore a lot of responsibilities.
“His mother said to him, ‘I need help, and you’re the only one I can count on,’” she said. “So from the time he was about 10 years old, that responsibility was something he took very seriously.”
Capone left school in the sixth grade and worked odd jobs to help his family. His criminal resume began early, as he also got involved with a local street gang as a boy. He eventually landed a job at a saloon called The Harvard Inn, owned by a gangster named Frankie Yale. It was there he met another established gangster named Johnny Torrio.

“He moves up eventually from dishwasher to bartender and then begins to find himself in a position where he’s doing some…more dangerous work for guys like Torrio and Yale,” Jonathan Eig, author of Get Capone, told Chicago Stories.
At the age of 18, he met Mae Couglin. She became pregnant not long after, and they married after their son Albert (nicknamed Sonny) was born.
“Suddenly, making money becomes a lot more important,” Eig said.
Sonny was born with congenital syphilis. Capone had passed the STD to Mae, having picked it up from his numerous affairs – and frequent trips to brothels. One day, after hitting on a woman reportedly at The Harvard Inn, Capone was attacked by the woman’s brother. The brother slashed Capone’s face with a knife. He got the nickname Scarface – “a nickname he, of course, despised,” Eig said.
Capone eventually followed Torrio to Chicago, where he began to bring in more money. It was in Chicago that Capone hit the big time, working his way up as the right-hand man to Torrio. Later, after Torrio was nearly assassinated, spent time in prison, and then returned to New York, Capone took over as the boss. Despite being a gangster associated with a growing list of felonies, Capone was never shy about the public attention he received. He gave interviews to newspapers and was often photographed as a man about town.

“Al Capone really appeared to be an individual who wanted all of the glitz and glamor of media attention, but not necessarily the consequences that [would later] come from that,” FBI Special Agent and Public Affairs Officer Siobhan Johnson told Chicago Stories. “He was known for being very flamboyantly dressed, brightly colored suits, his trademark hat.”
Diane Capone said she thinks her grandfather liked having the respect and attention. “It is pretty intoxicating, I think, for a person who all of a sudden begins to have a certain amount of power,” she said.
But life wasn’t always pretty for Capone. He led the South Siders during the years of bloody disputes that came to be known as the Beer Wars. One dramatic, violent event would turn the tide of public opinion.
Catching Capone
The St. Valentine’s Day Massacre in 1929 marked a shift in the public’s tolerance for organized crime. After seven men linked to Bugs Moran’s North Side gang were gunned down in a Lincoln Park garage, the press attention turned sour. The bloody images that were printed in the newspapers shocked readers.
“Once he started to lose control of public opinion, that news attention turned negative, and it stayed negative. That certainly hurt him as he went along,” Johnson said.
By this point in Capone’s reign, Herbert Hoover, the newly elected president, made fighting crime and putting Al Capone behind bars a top priority for his administration. Simultaneously, the Chicago Crime Commission dubbed Capone “Public Enemy No. 1.”
Prior to this point, Capone “was never convicted of murder. He was never convicted of breaking the bootlegging laws, although he [broke bootlegging laws] thousands of times,” said John J. Binder, author of Al Capone’s Beer Wars. But that was about to change.
A few weeks after the St. Valentine’s Day Massacre, authorities subpoenaed Capone from his Miami home to appear in court in Chicago on a bootlegging charge. Capone claimed he was too sick to travel, but when FBI agents showed up in Florida, they found that Capone had lied. According to the FBI, “When he was supposedly bedridden, Capone was out and about – going to the race tracks, taking trips to the Bahamas…his health was just fine.” He was arrested for contempt of court in March of 1929. Though he bailed out of jail that time, the trouble would continue to grow for Capone.

In May, Capone was arrested again, this time in Pennsylvania on a concealed weapon charge. He was sentenced to a year in prison. However, with Capone’s connections and money, prison looked a little different for him than it did for the average criminal.

“Capone had a way of winning over his wardens,” Eig said. “He would let them borrow his car. He would pay them to allow him certain luxuries.”
But an even bigger headache for Capone was brewing while Capone served his relatively cushy prison sentence. Eliot Ness, an agent for the Bureau of Prohibition, had begun raiding Capone’s bootlegging operations. However, Ness, who is portrayed in the 1987 film The Untouchables, gets perhaps too much credit for taking down Capone.
“Eliot Ness gets a lot of attention because he’s breaking down the doors of breweries,” Eig said. “He’s very good at public relations, but he’s not making a dent in the Capone operation. There’s no way to really tie him to the bootlegging because there [are] no books.”
Instead of murder or bootlegging, a far less flashy crime would be the final blow to Capone: tax evasion. A U.S. attorney named George E. Q. Johnson and a forensic accountant for the U.S. Treasury Department named Frank Wilson searched for evidence that Capone owed money to the IRS for unreported gambling income. They sought out a paper trail.
“I love the accountants who went after Capone because they’re just these humble number- crunchers,” said Eig. “They’re literally just going through boxes, and they find a guy who was one of the accountants, and they put the screws to him…He cracked and said he was willing to help and told them where they could find some of the books.”
They found ledgers with Capone’s name on them – proof that he had income he wasn’t paying taxes on. In the summer of 1931, Capone was indicted by a federal grand jury for income tax evasion. Along with his associates, Capone was also charged with 5,000 counts of violations of the Volstead Act (the national Prohibition law). Initially, fearing their evidence wasn’t quite strong enough, Johnson’s team offered Capone a deal: if he pled guilty, he’d serve only two and a half years in prison. But Judge James Wilkerson rejected the plea bargain, and the case went to trial. A jury was assembled and then – after fears that Capone had tainted some of the jurors – reassembled. They found Capone guilty of income tax evasion. Wilkerson sentenced Capone to 11 years in prison.
Capone spent the first two years of his sentence in a prison in Atlanta. Then a new prison opened. It was called Alcatraz.
“Once that prison was created, they would of course want to populate it with those that Americans thought were at the top of the public enemy list,” Siobhan Johnson said. “He experienced a much harsher existence than he had at any prison before.”
By 1939, several years into his sentence, Capone’s health was reportedly failing. The neurological effects from the long-term syphilis he contracted as a young man had begun to affect him. He was granted a medical release from prison and returned home to his family in Florida. According to his granddaughter Diane, Capone had embraced his Catholic faith again in prison, and when he was out, went to weekly mass. But after years in prison and deteriorating health, some thought Capone had lost his mind.

“Some people who he’d known in Chicago came to visit him. And they thought he was losing his mind, that he was batty,” Diane Capone said. “My grandmother…was offended. And [Al Capone’s] remark to her was, ‘Let ’em think whatever they want. It’s my ticket out.’”
Al Capone died in 1947 from complications of a stroke and pneumonia. His very name still evokes seedy organized crime and brutal mob violence, but scholars and other experts won’t go as far as calling Capone a sociopath or a monster. Capone was more complex than that.
“It’s not necessarily fair to call someone a monster. From our point of view, we’re not in the business of name calling,” Johnson said. “What is clear is that he violated federal statutes. He committed crimes. We collected evidence that showed that he committed those crimes, and he was forced to pay for those transgressions. He hurt the populace. And there are consequences for that.”