Al Capone: Gangster of a Generation

By: Nathan Chandler
Image: Youtube

About This Quiz

When you think of American mobsters, you think of Al Capone. He wasn't just a criminal -- he was a superstar. That is until karma caught up to him. How much do you know about Capone?

Al Capone got rich as a member of organized crime. How did he make most of his money in Chicago?

Capone was a gangster in the time of Prohibition. He made a killing (figuratively and literally) by smuggling booze all over the area.

How did Capone feel about violence?

Alphonso (his given name) was mostly a crooked businessman. Violence was just a part of the job for him.

Capone was often called "Scarface." What happened to his face?

A man at a bar slashed his face due to a perceived slight. The two men mended fences and the man eventually became Capone's bodyguard.

"Scarface" became a mob boss in Chicago. Where did he grow up?

He made a name for himself in Chicago. But Capone actually grew up in New York City and was part of the infamous Five Points Gang.

How did Capone end up Chicago?

A gangster named Johnny Torrio was running a bootlegging operation in Chicago and asked Capone to help him. Scarface was happy to be a part of the underground operation.

In 1925, Capone became leader of the Chicago mob after Torrio was hurt. What happened to Torrio?

Torrio was nearly assassinated by a rival. Badly hurt, he decided he was done being a gang leader and he moved back to Italy.

Early in life, Capone contracted which disease?

Like many gangsters, Capone frequented prostitutes, one of whom gave him syphilis. The disease wracked his body later in life.

Capone's father was a gangster.

His dad was a barber and his mom was a seamstress. Capone wasn't born into the gangster life ... he chose it.

Booze was by far Capone's biggest moneymaker. About how much did he make each year from bootlegging?

In the 1920's, it was simply an incredible sum of money. Capone made roughly $60 million per year making and smuggling booze.

Capone was a notorious gangster. How did he approach public life?

He wasn't shy about flaunting his wealth or criminality. Capone lived in broad daylight thanks in part to his too-cozy relationships with city authorities.

In school, Capone misbehaved and was struck by an angry teacher. What did Al do in response?

Capone decided to punch his own teacher, who then delivered an epic beatdown on his student. Capone never went back to school.

At one point, Capone swore off the gangster life. Why?

Al had a kid and got married. He took up a straight job and left behind gang life, but only until Torrio invited him to Chicago.

Capone is often blamed for ordering the St. Valentine's Day Massacre, in which how many gang members were killed?

In 1929, seven rival gang members were executed. Capone was never formally charged but many historians believe that he ordered the killings.

Everyone knew Capone was making tons of money in crime. Why couldn't the cops catch him?

Al paid for everything with cash ... piles and piles of cash. His blatant disregard for the law was infuriating to many law-abiding folks.

The press treated Capone like a fun-loving celebrity. So why did the public's opinion of Capone begin to sour?

Capone used horrific violence to stamp out his competition. The star-struck public became much more leery of the gangster's glib sheen.

Capone's men often killed civilians in order to terrify the population.

Civilians weren't generally targets, and the public knew it. It's one reason Capone became a celebrity in spite of his criminality.

Scarface once beat three men nearly to death using what?

By some accounts Capone discovered a betrayal. He sought retribution by beating three gangsters with a baseball bat, a story that added greatly to Capone's violent reputation.

Which U.S. President made catching Capone a top priority?

Capone became a national outlaw. President Herbert Hoover pressed his law enforcement team to find a charge and make it stick.

In 1930, many people were fed up with Capone and his public antics. He earned which nickname?

He was dubbed "Public Enemy No. 1," and as his star continued to rise, Capone garnered more and more attention from the authorities.

In May 1929, Capone and his bodyguard were arrested in Philadelphia on what charge?

Both were carrying weapons. Capone was actually convicted and sent to prison for nine months.

In 1929, Capone was subpoenaed to court and he skipped the hearing claiming that he was sick. Where was he, really?

Capone produced a doctor's note saying he was sick. But unluckily for him, he was spotted frequenting a local race track, leading to a contempt of court charge.

Capone frequently dodged the law. He was finally convicted of which crime?

Scarface got away with murder, literally. But the government eventually nailed him for tax evasion.

What sort of punishment did Capone receive for tax evasion?

Capone gave the feds all sorts of problems during his reign, but they finally convicted him of tax evasion. He was given an 11-year prison sentence, and his appeals were denied.

Why was Capone moved from an Atlanta prison to the notorious Alcatraz?

Capone wanted special treatment in prison, so he bribed the guards. He was caught and sent to the much tougher Alcatraz prison near San Francisco.

What was Capone's reaction to his prison sentence?

His lawyers figured he'd receive maybe a couple of years, tops. So when the 11-year sentence was handed down, everyone, from the public to Capone himself, was completely shocked.

How did Capone fare in prison?

His fearsome reputation didn't do him much good in prison. Capone was sometimes mistreated in prison as other inmates mocked the fallen star.

As Capone served his prison sentence, what happened to him?

It was an ominous slide for the once-powerful criminal. The syphilis he contracted as a young man began settling into his brain, causing severe dementia.

Capone brutalized a city. How did he die?

In part due to syphilis, Capone's health suffered when he went to prison. He had a stroke and then a heart attack killed him.

Before he died, a doctor said that Capone's mental status had deteriorated to a person of what age?

Perhaps it was a sort of karmic justice. By the end of his life, syphilis had reduced Capone's mental age to the equivalent of a 12-year-old child.

What was the name of the operation that Capone ran?

Capone will always be remembered as the tempestuous leader of the Chicago Outfit. He lived a glamorous gangster life, but in the end it all caught up to him.

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