Al Capone: The Rise and Fall of Scarface

Al Capone is America’s most infamous mobster. He is known for his involvement with the Chicago organized crime syndicate, where he ruled during prohibition.

Jun 12, 2023By Madison Whipple, BA History w/ Spanish minor

al capone rise and fall of scarface


Al Capone was a mobster who worked with the Outfit syndicate of the Italian-American mafia during the Prohibition era. Capone was infamous for his conglomerate of illegal business ventures and for being one of the most brutal mob bosses the country has ever seen. He elevated Chicago as the hub for mafia activity during the 1920s and ruled with an iron fist. His fortune was massive, and his network of mobsters extended far and wide. Capone was a typical “gentleman mobster” who always used a middleman and was always in the right place at the right time. This is the story of his life, conviction, death, and legacy.


The Beginning of Al Capone 

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Portrait of Al Capone in 1925, via The Library of Congress


Alphonse Gabriel Capone was born in Brooklyn, New York, on January 17, 1899. His parents were Italian immigrants who arrived in the United States in 1893. His father, Gabriele, was a barber and his mother, Teresa, was a seamstress. When the Capones arrived in New York, they already had two small children, and Teresa was pregnant with their third. In all, Capone had eight siblings: six brothers and two sisters. Two of Capone’s brothers, Ralph “Bottles” Capone and Salvatore “Frank” Capone, would go on to work with him in some way, through direct involvement with the mob or by helping with his bootlegging business.


Capone attended a parochial Catholic school, and while he was a good student, he struggled with the strict rules. He was expelled at 14 for hitting one of his female teachers in the face. He then worked odd jobs around the city and played semi-professional baseball. By the time Capone was 14 years old, he had met Johnny Torrio, a New York City gangster whom he would consider a mentor. Torrio sought to transform the business of organized crime from being a grisly and violent culture to a corporate one. Torrio introduced Capone to the crime world, and eventually, Capone and Torrio were working with some of the most significant gangs in New York.


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Al Capone and his son, Albert Francis “Sonny” Capone, via The New York Times


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Al Capone began working with different street gangs in 1918. He was involved with the Junior Forty Thieves, the Bowery Boys, the Brooklyn Rippers, and the Five Points Gang. He was employed by a racketeer named Frankie Yale, who mentored Capone at his bar in Coney Island called the Harvard Inn. During this time, a man slashed Capone in the face after inadvertently insulting his sister. This injury gave him the nickname “Scarface,” which he would be known by for the rest of his life. Capone hated it despite being known by the name and actively tried to hide his scar in all photographs.


In 1918, Capone married Mae Coughlin, an Irish-American Catholic, two years his senior. However, Mae and Al both listed their ages as 20 on their marriage certificate. The couple’s first and only child, Albert Francis “Sonny” Capone, was born three weeks before their wedding. Al settled down for a while, becoming a bookkeeper. However, after his father’s sudden death, Al returned to working with the mob. Mae was never involved with her husband’s crimes and actively discouraged their son from becoming involved.


Becoming the Boss

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Al Capone and his associates in Hot Springs, Arkansas, via The Guardian


The Capones moved to Chicago in 1919 at the behest of Joe Torrio, who was working as an enforcer for James “Big Jim” Colosimo, an essential boss in the Italian American organized crime syndicate. After Colosimo’s murder in 1920, Torrio took over as the boss of the largest organized crime group in the city. Whereas Colosimo reportedly refused ever to be involved with the bootlegging business, Torrio began involving his group in the operations of the illegal alcohol industry soon after his ascension to the highest seat. He attempted to be known for his settling of disputes, but he misstepped in this role when he ordered the hit of the rival North Side group’s leader. The successors of the North Side group, including Bugs Moran, were eager to enact revenge on the Italian group.


In 1925, Torrio was shot multiple times on his way home from an outing. He survived but, after recovering, retired from his role as boss of the group, which had now become known as The Outfit. Torrio handed the reins to Capone, who dove headfirst into the role. Capone was head of an organization that ran illegal breweries, gambling rackets, and prostitution rings, all with the protection of political and law enforcement allies.


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Capone’s headquarters, the Hawthorne Hotel, in Cicero, Illinois, via The Chicago Tribune


This protection was only furthered when The Outfit moved their headquarters to Cicero, Illinois, where Capone and several of his men, including his brothers, intimidated and bribed their way into public office. They were able to set up many more racketeering businesses, as they were the law now. This takeover made it harder for the North Side Gang to eliminate members of Capone’s Outfit, but it did not stop it. Several attempted and successful hits were carried out when he lived in Chicago. Capone never went anywhere without an armed detail, although he never carried a weapon himself.


Capone sought to retain an image of himself as a respectable businessman and a contributing community member. Although he was known to attempt peacemaking, gang violence between Chicago rivalries increased steadily until Capone and his entourage felt the need to avoid Chicago at most times. Because of the violence, Capone moved his family to Miami, Florida, where he purchased a 10,000-square-foot mansion from the Anheuser-Busch family.


Capone was known for being flashy; having custom suits, expensive jewelry, and imported cigars were all trademarks of the Outfit boss. Capone was also well known for evading any charges during this time, as in every case he was suspected, there was too little evidence to convict him. Even when the police, frustrated, cracked down on Capone’s brothels and gambling dens, Capone gave himself willingly to the department. There was no evidence for any crimes that Chicago police could hold him on, thus setting Capone and his properties free.


Saint Valentine’s Day Massacre 

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The wall against which seven men were killed on February 14, 1929, via The Mob Museum


Al Capone saw himself as a peacemaker, but he was also a practical, if not paranoid, leader of the Chicago Outfit. Capone was reportedly worth $100 million in 1927, equal to $1.7 billion today. Capone had lucrative businesses and a lot to lose. He was rivaled only by the North Side Gang, whose leader, Bugs Moran, presented as a thorn in Capone’s side. Moran’s businesses were booming as well as Capone’s, but hijacking illegal booze operations was common on both sides of the aisle. As the story goes, Capone was tired of dealing with the North Side Gang and wanted their businesses for himself. The way to do this was to get rid of Bugs Moran. Capone ordered a hit on Moran. On February 14, 1929, Capone was safely tucked away in Florida while four of his henchmen, dressed as police, brutally murdered seven of Moran’s men. This would come to be known as the St. Valentine’s Day Massacre.


al capone florida estate
The Florida estate where Capone was living at the time of the St. Valentine’s Day Massacre, via Creative Loafing Tampa


The massacre is one of the most notorious in United States history, but Capone may not have committed it. In fact, no one was ever convicted of the crime. Herbert Hoover and the FBI could find no evidence that Capone ordered the hit. The most obvious information that cleared him was that Moran himself was not even killed.


However, a few years later, a gangster with ties to Capone was found with the two machine guns used in the killings. The gangster, Fred “Killer” Burke, was convicted on a separate charge (killing a police officer in Michigan after the Massacre) and died in prison. This begs the question of why Capone’s associate, who owned weapons used in the St. Valentine’s Day killings, was never convicted of that crime. The simple answer is that the federal government wanted the guilt to hang on Capone, even if they had no evidence to arrest him, which it still does today.


Modern scholars believe that the killings of February 14th, 1929 may have been due to a myriad of things, from Moran himself ordering the hit to real police officers carrying out the attack in retaliation for the murder of a fellow officer’s son. However, in the popular zeitgeist, the St. Valentine’s Day Massacre is tied to Capone, and it characterizes the violence of Prohibition-era Chicago.


Arrests, Death, & the Legacy of Al Capone

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Al Capone’s mugshot from 1939, via the FBI


Capone was arrested several times, including in May of 1929, when he was arrested and convicted for carrying a concealed handgun in Philadelphia. Capone served nine months in Pennsylvania’s Eastern State Penitentiary for the crime. He was also arrested in Miami for vagrancy, and although he was sentenced to six months, he never served time for the charge.


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Al Capone on his way to Atlanta Federal Penitentiary in 1931, via PBS


In 1931, the Federal Government figured out a way to put Capone behind bars for longer than he’d ever served. They had failed to do so several times, although it is likely that Capone committed or instigated several violent crimes. The crime that finally got him, however, was financial. Capone’s reported income did not align with his payment of taxes. His lavish lifestyle was significantly more expensive than his supposed and taxed income. On June 5, 1931, Capone was indicted for 22 counts of federal tax evasion and 5,000 violations of the Volstead Act, the laws regarding Prohibition. His trial was presided over by a particularly harsh judge, who sentenced Capone to 11 years in prison for his crimes rather than take a plea bargain of two and a half years that Capone’s lawyers relied on.


al capone fbi record
The FBI file against Al Capone, via the FBI


Capone was sent to Atlanta US Penitentiary, where he was first formally diagnosed with syphilis and gonorrhea. He also experienced perforation of his septum and withdrawal symptoms due to cocaine addiction. Capone was moved to Alcatraz in 1934, where he played banjo in the prison band, the Rock Islanders. Capone’s health worsened considerably during his time at Alcatraz, and he spent the last year of his time in prison in the hospital wing. It was in 1938 that prison doctors diagnosed him with syphilis of the brain, which mimics dementia in its effect. His mental capacity, according to doctors, was that of a twelve-year-old during this time. In 1939, Capone was released based on his poor health at his wife’s appeal.


Capone lived the rest of his life with his wife and grandchildren on his Palm Beach estate until his death from heart failure in January of 1947. He was laid to rest in Chicago. The Outfit remained at the center of Chicago’s organized crime syndicate, albeit more underground, as the group took heed of how Capone’s notoriety led to his demise.


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Al Capone’s casket being carried to his resting place in 1947, via The Chicago Tribune


Capone is the basis for the classic imaginings of a gangster in American lore. His pin-striped suit and fedora are notorious as constructions of characters based on him. He is the subject of many films, books, shows, and articles. Loose interpretations of every aspect of his character have been the basis for many more mob-related facets of popular culture. In life, he was once considered the most notorious gangster in the country, and in death, he is, without a doubt, America’s most infamous mobster of all time.

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By Madison WhippleBA History w/ Spanish minorMadison is a contributing writer with specialties in American and women’s history. She is especially interested in women’s history in the context of the American Civil War. In her free time, she enjoys going to museums, reading, and jogging.