Was Al Capone America's Greatest Criminal?

By Willy Maher
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Photo Courtesy: Donaldson Collection/Getty Images

If gangster lore sparks your imagination, then Al Capone is probably a name you know quite well. Throughout his life of crime, Capone was responsible for many brutal acts of violence, including the infamous St. Valentine's Day Massacre that took place in Chicago in 1929. His Chicago-based organized crime operation reportedly brought in $100 million annually.

Capone gravitated to the spotlight at a time when most gangsters tried hard to keep their names and their faces off the front page. His fascination with fame could be one reason his legacy endures to this day. He is certainly one of the country’s most famous gangsters, but does he rank as America’s greatest criminal? You be the judge!

Early Life in New York

Al Capone was born in 1899 in Brooklyn, New York. He was the son of Italian immigrants who made the journey to America in hopes of establishing a better life for themselves and their eight children.

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Photo Courtesy: Chicago Bureau/Wikimedia Commons

His mother worked as a seamstress, and his father worked as a barber. Capone's early life in New York was nothing out of the ordinary for Italian immigrants during the time. There was certainly nothing about his childhood that would have tipped anyone off that he would eventually embark on a life of crime.

Expelled from School

As a child, Capone was reportedly a very good student when he went to elementary school in Brooklyn. Things took a downturn by the sixth grade, however, when he started skipping school and hanging out by the Brooklyn docks instead.

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Photo Courtesy: Chicago History Museum/Getty Images

Capone was ultimately forced to repeat the sixth grade due to his poor performance in school. Things got even worse for him at school after a teacher struck him for his misbehavior, and he hit back. In response, the principal of the school gave him a beating, and he never again returned to school.

Meeting Johnny Torrio

The Capone family moved to the outskirts of the Park Slope area of Brooklyn around the time that he got kicked out of school. This was the area they lived in when Capone's future life really started to take shape. It was there that he met Mary "Mae" Coughlin, who eventually became his wife and the mother of his only child.

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Photo Courtesy: New York Police Department/Wikimedia Commons

He also met a man by the name of Johnny Torrio in the Park Slope neighborhood of Brooklyn. Torrio went on to become Capone's mob mentor, and the man who introduced him to his life of crime.


Running Errands for Johnny Torrio

Torrio was running a gambling and numbers operation at the time, and a young Capone began working for him by running small errands. Torrio left the Brooklyn area for Chicago in 1909, but the two remained close, even after his departure and relocation.

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Photo Courtesy: Bloodletters & Badmen/YouTube

After his mob mentor left the area, Capone chose to stick with legitimate employment for a time. He worked in factories and worked as a paper cutter, and he eventually got involved with some of the street gangs in Brooklyn. Capone got into some scraps with the gangs, but it was never anything serious.

Harvard Inn on Coney Island

From 1909 to 1917, Capone's involvement in the criminal underworld was limited to nothing more than getting into an occasional fight and participating in mild street gang activity. As he was still good friends with Torrio, however, he eventually found himself once again hanging out with underworld gangsters.

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Photo Courtesy: David Reilly/Wikimedia Commons

Torrio introduced Capone to a gangster by the name of Frankie Yale in 1917. Yale hired him to work as a bartender and a bouncer for him at the Harvard Inn on Coney Island. The job brought about many changes in Capone's life and even led to him gaining the scary nickname "Scarface."

Earning the Nickname "Scarface"

It was while he was working for Yale at the Harvard Inn on Coney Island that Capone came to be known by the intimidating nickname he carried with him throughout the remainder of his criminal career. He supposedly made a rude comment to a woman at the Harvard Inn that led to an altercation between her, Capone and her brother.

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Photo Courtesy: New York Times Co./Getty Images

The woman's brother punched Capone as a result of the comment, and she slashed him across the face, leaving three noticeable scars. The attack and the subsequent scars first led to some of his fellow gangsters calling him "Scarface."


Married with Children at 19

Al Capone's first and only son, Albert Francis, was born when he was only 19 years old. Capone married Mae Coughlin just weeks after the child was born. Johnny Torrio served as the boy's Godfather, an important Italian tradition.

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With Capone then a husband and a father, he tried to do right by them and provide for them by doing honest work. In that quest, he moved to Baltimore and began to work as a bookkeeper for a construction company. However, as with every other attempt Capone made to lead a law-abiding life, this effort to abide by the law didn’t last.

Father's Death

Although it appeared — at least for a while — that Capone intended to settle into a life of honest employment, something happened in 1920 that sent him right back to a life of crime. That was the year his father died of a heart attack.

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Photo Courtesy: Chicago Tribune/Getty Images

Not long after the death, Torrio invited Capone to work for him in Chicago, and he decided to take him up on the opportunity. His life as a family man working honest jobs was over, and his move to Chicago in 1920 firmly set him on a course to infamy.

Moving to Chicago

When Capone joined Torrio in Chicago, he discovered his mob mentor was running a lucrative criminal business. Torrio was involved in all sorts of underworld enterprises, including gambling and prostitution. It wasn’t long before a new business opportunity opened up for Capone.

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A famous — and much hated — law passed that year that played a major role in the shaping of Al Capone's criminal career as well as the establishment of numerous other underworld families across the country. In 1920, Prohibition banned the sale and consumption of alcohol in the United States. Although it was unpopular, the law remained in place until 1933, which led to a multi-million-dollar industry related to illegal alcohol during that 13-year period.


Introduction of Prohibition

Prohibition in the United States lasted from 1920 until 1933 and largely came about due to the concerns of citizens who saw alcohol as a societal problem. In fact, by the time Prohibition began nationwide in 1920, many communities and states had already taken it upon themselves to ban the sale and consumption of alcohol in their region.

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The ban on alcohol allowed gangsters like Capone and Torrio to develop lucrative bootlegging operations. Many criminal underworld operations saw a large expansion in their operations and their territories as a result of the money they made bootlegging during this time.

Partnering in a Lucrative Bootlegging Operation

Prohibition ushered in new and lucrative times for the criminal underworld, as formerly law-abiding citizens turned to the black market to purchase the alcohol they had previously consumed legally. With a whole new crop of customers and money coming in, Capone used his street smarts and his expertise with numbers to run operations in Chicago.

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Photo Courtesy: Archives of Ontario/Wikimedia Commons

Torrio noticed his skills and quickly promoted him to partner. The move officially made Capone a major player in the Chicago underworld. He soon started to demonstrate tendencies that Torrio did not, however.

A High-Profile Gangster

In contrast to Torrio and many other gangsters of the era, Capone wasn’t interested in keeping a low profile. Rather than stay under the radar and avoid trouble, he developed a reputation as a drinker and a troublemaker. Other gangsters avoided such behavior out of fear it would attract attention from the authorities — possibly even get them arrested.

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Capone didn't seem to mind the attention, however. In fact, there was nothing low profile about him as his Chicago bootlegging operations took off. From the beginning, it was his tendency to bask in the spotlight to cement his name in pop culture.


Arrested for Drunk Driving

As the 1920s continued, so did Capone's drinking and troublemaking. He was arrested for the first time in his life after he drove intoxicated and hit a parked taxi cab. You weren't allowed to consume alcohol at all in the 1920s, let alone operate a vehicle while drunk, but Capone didn’t face negative consequences as a result of driving while inebriated.

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Photo Courtesy: FBI/United States Bureau of Prisons/Wikimedia Commons

Capone's literal partner in crime, Johnny Torrio, used his connections in the Chicago municipal government to get the charges dismissed. The incident was further evidence of the fact that Capone saw no merit in keeping a low profile.

Moving His Family to Chicago

After his arrest for drunk driving, Capone vowed to clean up his act — a promise he had made before and never kept. To support him, he brought his whole family out to Chicago from Brooklyn. This included both his wife and his son as well as his mother, sister and younger brothers.

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Capone bought a house in a middle-class Chicago neighborhood for them all to live in together. In 1923, municipal politics in Chicago threatened to bring down Capone's ever-expanding empire. In fact, the change in municipal politics threw Capone's criminal operations into turmoil for the next few years.

Election of William Emmett Dever

William Emmett Dever was elected mayor of Chicago in 1923. Capone and Torrio were concerned by his election, primarily because he had campaigned on a promise to rid the city of corruption and criminal activity. Torrio and Capone opted to move just outside of Chicago city limits in response to his election.

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Photo Courtesy: Public Domain/Wikimedia Commons

They moved to the suburban area of Cicero and continued with their bootlegging and other criminal operations. In 1924, a different municipal election in Cicero again threatened their operations. That time, Capone and Torrio decided not to move again to escape the problem.


The 1924 Cicero Election

Instead of moving the base of their operations outside of Cicero as they had done in Chicago when William Emmett Dever was elected, Torrio and Capone opted to use intimidation tactics on the day of the election to ensure a gangster-friendly candidate was elected. It seemed like a logical plan, right?

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The election was held on March 31, 1924, and the intimidation tactics that were used got entirely out of hand and even resulted in some voters being shot and killed. In response, Chicago sent police to Cicero to handle the situation. As a result, they shot and killed Capone's brother, Frank Capone.

Chicago Police Gun Down Frank Capone

Frank Capone was four years older than his brother, Al, and he worked with him in the Chicago division of the mob. On election day in Cicero in 1924, citizens petitioned the Chicago police to send officers to the polls to stop the Chicago outfit from intimidating voters.

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Photo Courtesy: Chicago Tribune/YouTube

Several inquests into what happened that led to the shooting of Frank Capone took place. Some witnesses said the gangster never opened fire, but the police claimed Frank Capone fired the first shots. What is known for sure is that Frank Capone died as a result of multiple gunshot wounds inflicted by the police.

Johnny Torrio Returns to Italy

The following year (1925), rival mobsters made an attempt on Torrio’s life. The experience led Torrio to decide to leave the businesses he built behind and return to Italy. He had been Al Capone's mentor in the criminal underworld and had attempted to steer the gangster away from activities that could bring about his downfall.

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Photo Courtesy: Bettman/Getty Images

As a result of Torrio's departure, Capone inherited full control of the Chicago operations. Before heading back to Italy, Torrio again advised him to keep a low profile. Once again, his advice fell on deaf ears.


Living a Luxurious Life in Downtown Chicago

Rather than heed the advice of his mentor, Al Capone began enjoying a very luxurious lifestyle in the public view as soon as Torrio returned to Italy. Once he was in full control of the Chicago bootlegging operations, he felt like he was on top of the criminal underworld.

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Photo Courtesy: Daniel Schwen/Wikimedia Commons

Capone moved into a fancy suite at the Metropole Hotel located in downtown Chicago, and then he moved the headquarters of his operations there. He only spent money in cash to avoid any problematic paper trails. The media reported that Capone's operations were bringing in $100 million annually.

$100 Million in Revenue Generated Per Year

As both the 1920s and Prohibition continued, Al Capone's bootlegging operations and other criminal enterprises flourished. Newspaper articles at the time claimed that his operations generated $100 million in revenue per year. He was spending lavishly, but he had plenty more coming right back into his bank accounts.

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Capone's lavish lifestyle was covered in the media, and he became an increasingly recognizable public figure. It was also during this time that public sentiment towards gangsters became increasingly positive due to the general public’s hatred of Prohibition. Many citizens developed sympathy and even respect for the bootleggers who kept them supplied with alcohol.

Robin Hood Figure

The media began to report on Capone's every move as he became increasingly entrenched in the public consciousness. The image that was presented through the media often portrayed him as a generous person. He was seen as someone who gave back to the community where he lived, which further added to his public appeal.

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Photo Courtesy: U.S. National Archives and Records Administration/Wikimedia Commons

As anti-prohibition sentiment increased in society, there was an equal amount of positive sentiment directed at people like Al Capone. He became something of a Robin Hood figure as he opened soup kitchens and engaged in other charitable efforts around town. In a way, these efforts blinded the public from his more violent activities.


Murder of William McSwiggin

In 1926, a mistake was made that cost Capone's operations dearly. He spotted two of his rivals in Cicero and gave the order for his men to shoot them down. What he didn't know was that a local prosecutor was the third man walking with the other two men.

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The man's name was William McSwiggin, and he had a scary nickname of his own: "The Hanging Prosecutor." McSwiggin was shot and killed with the other two men, leading the public to demand justice. Capone had been in the public's good graces for years, but the murder of a government employee — particularly an innocent one — changed that.

Police Retaliation

Following the murder of William McSwiggin, the police were even more motivated to go after Capone. The authorities had no evidence to charge him with the murders, but they persistently focused on raiding Capone's businesses to look for evidence.

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They never did find evidence of the murder, but what they did find was information they later used to bolster charges against Capone for not paying income taxes. As everyone knows, it’s illegal to not pay income taxes on all money earned, even if that income is obtained through illegal means. In response to the increased police pressure, Capone helped organize a conference for underworld figures in Atlantic City.

The Atlantic City Conference

Due to the increased police pressure that Capone's operations experienced in the late 1920s, he facilitated a meeting of organized crime leaders in the United States. The summit was held May 13-16, 1929, in Atlantic City.

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The main focus of the conference was to discuss how the country's criminal organizations could avoid violent conflicts that garnered increased public attention and police focus. The idea was that if the crime organizations across the country could stop their in-fighting, they could increase their profits as police pressure lessened. While an agreement was made, it only lasted a couple of months.


St. Valentine’s Day Massacre

In 1929, with Capone still dominating the alcohol black market in Chicago, other racketeers were vying for a share of the bootlegging pie. One of the men looking for a bigger share of the black market was Bugs Moran.

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Rumor had it that Moran was after Capone's top hitman at the time, "Machine Gun" Jack McGurn. In response, McGurn's gunmen posed as police and murdered seven of Moran's men in cold blood in a parking garage. Bugs Moran escaped beforehand, however. The media immediately blamed Capone for the actions and dubbed him "Public Enemy Number One."

Indicted for Tax Evasion

Following the St. Valentine's Day Massacre, President Herbert Hoover had the federal government increase their efforts to go after Capone. As a result of a Supreme Court ruling in 1927, all income gained in the United States from illegal activities still had to be taxed. Because Capone had not been paying taxes, he was therefore guilty of tax evasion.

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Photo Courtesy: FBI/United States Bureau of Prisons/Wikimedia Commons

The federal government used evidence obtained during raids of his businesses to charge Capone with 22 counts of income tax evasion. The charges were formally made on June 5, 1931. A plea bargain deal was rejected, and the case went to trial.

Sent to Alcatraz

When the courts rejected Capone's plea bargain deal, he withdrew his guilty plea and attempted a new strategy to get off on the charges. He used bribery and intimidation tactics on the jury in hopes that they would ultimately render a decision in his favor.

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Photo Courtesy: Tres calcetines/Wikimedia Commons

The judge presiding over the trial had a trick up his sleeve, however. He switched to an entirely new jury at the very last moment. Capone was then sent to prison for 11 years after the jury found him guilty. He was incarcerated in the infamous island prison of Alcatraz in 1934.


Living in a Mental Hospital in Baltimore

Capone began to suffer from ill health while he was in prison. It was during his stay in Alcatraz that doctors discovered he had contracted syphilis when he was younger. He had never been treated to slow the disease, so it grew worse and began to cause symptoms of dementia.

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As a result of his worsening health, Capone was released to a mental hospital in Baltimore in 1939. Other medical facilities refused to take him as a patient. He spent three years in the hospital before moving to Miami, where he spent the remainder of his life with his family.

Finals Days in Miami and Death

Capone moved to Miami after leaving the hospital in Baltimore. His health had continued to fail as a result of his syphilis and dementia. He suffered a cardiac arrest and died on January 25, 1947, just eight days after his 48th birthday.

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His death made front-page news with The New York Times featuring a headline that read "End of An Evil Dream." Capone's time as a major figure in the criminal underworld was controversial and sparks polarizing opinions. Some feel the repeal of prohibition in 1933 vindicated Capone, but others aren't as quick to ignore his many violent acts.

Legacy of Al Capone

Al Capone left behind quite a legacy when he died in 1947. He had been a major player in the criminal underworld in Chicago throughout the 1920s, but he was only 33 when he went to prison. His time at the top of the ranks of America's gangsters was only about seven years long, yet most of the country thinks of Al Capone as the face of organized crime during Prohibition.

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Several movies and TV shows have featured Capone, including 1959's Al Capone, HBO's Boardwalk Empire, TV's The Untouchables (as well as the movie), 1967's St. Valentine's Day Massacre and many more.