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Al Capone, like most wealthy men of the time, never went out in public without dressing properly.Wikimedia Commons
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Antonio "Tony the Scourge" Lombardo, a close associate and consigliere to Al Capone, was gunned down by rival gangsters on the corner of State and Madison Streets in Chicago.
The hit was in retaliation to Capone's supposed involvement in the killing of Frankie Yale.NY Daily News Archive/Getty Images
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This is just one of the countless people gunned down in the streets during Al Capone's decade of terror.Keystone-France/Gamma-Keystone/Getty Images
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Gangster Al Capone in the heavily guarded train that took him to federal prison.Bettmann/Getty Images
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A snazzily dressed Capone, unwavering in his gaze at the photographer.Bettmann/Getty Images
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Al Capone, happily posing for a mugshot upon arrival at Alcatraz. Aug. 22, 1934. San Francisco, California.Donaldson Collection/Michael Ochs Archives/Getty Images
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This car was designed specifically for Capone, and was fitted with bulletproof windows.
It reached speeds of 110 miles per hour.Bettmann/Getty Images
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Though Capone looks entirely at ease at the Federal Grand Jury hearings of his crimes, he's about to be convicted of tax evasion.Bettmann/Getty Images
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The FBI file on Al Capone from 1932, which showed most of his criminal charges as dismissed.
In the end, he was nabbed on 22 counts of tax evasion.Wikimedia Commons
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Al Capone with U.S. Marshall Laubenheimar, laughing on the train taking him to prison.Keystone/Getty Images
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A Capone family portrait during a leisurely picnic in Chicago Heights, Illinois in 1929.Chicago History Museum/Getty Images
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Capone's mugshot after getting arrested for vagrancy while visiting Miami Beach.
The governor had ordered sheriffs to run him out of state however they could.Wikimedia Commons
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Capone's final years consisted of fishing, having delusional chats with friends long dead, and chasing butterflies with his grandkids.Ullstein Bild/Getty Images
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Al Capone amongst the crowd like any other baseball fan, enjoying a White Sox ballgame. Comiskey Park, Chicago. 1931.Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum/Getty Images
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Al Capone glancing over attorney Abraham Teitelbaum's shoulder.
Teitelbaum himself would later be indicted on charges of evading $135,060 in taxes.Ullstein Bild/Getty Images
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Capone walking amongst the masses while being escorted by police and his own bodyguards around the time of his trial. 1931. Chicago, Illinois.Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum/Getty Images
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The spectators at Al Capone's trial were so fearful of retribution that they covered their faces in order to remain anonymous. 1931. Chicago, Illinois.Ullstein Bild/Getty Images
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Al Capone fishing aboard his yacht on the Florida coast.Archiv Gerstenberg/Ullstein Bild/Getty Images
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Al Capone playing cards while being transported to serve his prison sentence for tax evasion. 1931. Hulton Archive/Getty Images
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Al and "Sonny" Capone get their baseball autographed by player Gabby Hartnett while enjoying the front row seats at Cominskey Park.Pix Inc./The LIFE Picture Collection/Getty Images
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Al Capone and various attorneys in court. 1931. Chicago, Illinois. Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum/Getty Images
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Capone opened one of the very first soup kitchens in Chicago — "Big Al's Kitchen for the Needy."
It provided the unemployed with three meals per day, consisting of soup with meat, bread, coffee, and doughnuts.
The soup kitchen fed around 3,500 people per day.Bettmann Archive/Getty Images
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The Chicago Police opening up one of Al Capone's safes. 1931.Keystone-France/Gamma-Keystone/Getty Images
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The mobster who once welcomed photographers found himself completely camera shy behind bars.
Convicted of tax evasion, he quickly pulled his coat over his head. He was sentenced to 11 years in prison.Bettmann/Getty Images
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Al Capone signing a $50,000 bail bond in a federal building after being convicted of tax evasion.Topical Press Agency/Getty Images
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Al Capone, John Capone, and Mrs. Ralph Capone at a baseball game in 1931. Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum/Getty Images
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Capone traveled in style — even when his destination was federal prison.
The mobster was oddly calm during the ride, potentially due to the fact that he had a cushy prison cell waiting for him. October 1931.Hulton Archive/Getty Images
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Al Capone smiling in his seat. October 1931. Herald Examiner/Chicago Tribune/Tribune News Service/Getty Images
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Al Capone epitomized the style of 1920s gangsters — so much so that an outfit like this is still immediately recognized nearly a century later.Ullstein Bild/Getty Images
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Al Capone leaving federal court in 1931, during his lengthy trial for tax evasion.Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum/Getty Images
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The car carrying Al Capone zooms past the prison gates after the notorious mobster's release.David E. Scherman/The LIFE Picture Collection/Getty Images
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The St. Valentine's Day Massacre saw seven associates of Chicago's North Side Gang gunned down.
Al Capone was highly suspected of organizing the infamous hit.
Four of Capone's alleged associates were dressed in police uniforms. It was February 1929 when they entered the garage owned by gangster George "Bugs" Moran, and lured their targets in under false pretenses.Chicago History Museum/Getty Images
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Capone and his bodyguard, Frank Cline, covering their faces while being escorted by police detectives.
This was after they were arrested in Philadelphia for carrying concealed weapons.
From left to right in the front: Frank Cline, Detective Creedon.
From left to right in the back: Al Capone, Detective Malone.Bettmann/Getty Images
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Richard "Peg Leg" Lonergan was killed, allegedly by Capone's men, at the Adonis Social Club in Brooklyn.
For rival mobsters at the time, it seemed like nobody could get one over on Capone.NY Daily News Archive/Getty Images
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Al Capone leaving a cab outside the Chicago Federal Courthouse to attend his trial.
How Al Capone Rose From Brooklyn Street Thug To “Public Enemy No. 1” In 44 Pictures
Al Capone's name is arguably synonymous with the term "organized crime." The iconic 1920s gangster ruled the streets of Chicago during Prohibition — and was responsible for countless sales of illegal alcohol.
Along with fame and fortune, the infamous crime boss also encountered plenty of violence. When he was still a low-ranking wise guy, he got a serious knife wound on his cheek that earned him the monicker "Scarface" — a nickname he hated — before becoming head of the Chicago Outfit.
While Capone flaunted his wealth and complemented one home in Chicago with another in Florida, he also graciously gave back to the masses. This was a man who simultaneously had an estimated net worth of $100 million and opened one of the very first soup kitchens during the Great Depression.
Though Al Capone was most certainly a violent mobster whose days were comprised of crime, murder, and corruption, he was also ultimately an ailing grandfather. Having left his syphilis infection untreated for years, he eventually became delusional and largely incompetent in his 40s.
By the end, the big scary kingpin who is still depicted brutally bludgeoning people to death in literature and film had the mentality of a 12-year-old — and spent his days talking to invisible houseguests. The 44 photos above chronicle it all: from his ambitious rise to his inevitable downfall.
Al Capone's Early Life
Wikimedia CommonsThe Capone home in Chicago. 1929.
Born Alphonse Gabriel Capone in Brooklyn, New York on Jan. 17, 1899, the Italian American was raised by a barber from Naples and his wife. His parents, Gabriel and Teresa, arrived in New York in 1894 with thousands of fellow countrymen looking for opportunity.
The Capones ultimately had nine children — with Frank Capone most closely following in his brother's blood-soaked footsteps. From an early age, Al Capone had no patience for school, and was expelled from the institution after hitting a teacher when he was 14.
He had a short-lived career as a member of several New York gangs and also worked in a box factory at one point. It was after meeting Mary "Mae" Coughlin, a local Irish girl from an educated background, that he made her Mae Capone and accepted a fellow gangster's invitation to Chicago.
Al Capone: King Of Chicago
It was Johnny Torrio who taught Capone he should keep up appearances while racketeering. Under his tutelage, Capone moved his family to Chicago around 1920 and later colluded with Torrio to help murder his boss — James "Big Jim" Colosimo.
Before becoming Torrio's right-hand man and rising in the ranks, however, Capone worked as a bouncer for Colosimo's brothel and contracted syphilis from a prostitute. He was too ashamed to seek medical attention, which would later prove fatal. But in the meantime, he built himself an empire.
With Prohibition in full swing and Torrio retiring in 1925, Capone became head of the Chicago crime syndicate and had full reign of its gambling, prostitution, and bootlegging operations. The more bodies he left in his wake, the larger his reputation grew. Soon everyone in Chicago knew his name.
The most infamous incident of all, the St. Valentine's Day Massacre, saw Capone's alleged associates dress up as policemen and gun down the competition during a fake arrest. Though he'd soon be convicted of tax evasion himself, Capone's net worth was estimated to be around $100 million when he was in his prime.
Unfortunately, not a penny helped him treat the disease rotting his internal organs — nor did it prevent his untimely death.
The Death Of Al Capone
Wikimedia CommonsCapone's Palm Island home, which he bought in 1928 and lived in from 1940 until his death in 1947.
Capone had deteriorated so severely behind bars that his wife successfully lobbied for an early release due to "good behavior." At that point, the mobster was so far gone that he had been wearing his coat inside his heated Alcatraz cell. But he only worsened after moving to Florida for peace and quiet.
The mob had accepted his de facto resignation, and agreed to pay him a weekly $600 pittance just to stay quiet. For Mae, it was of the utmost importance to keep him shielded from the press — lest they portray him as a blabbermouth and consequent liability for the Outfit.
In the end, Capone was having delusional chats with friends long dead, which his family often went along with. Though he was one of the first people to receive penicillin treatments, it was too late at that point. His organs, including his brain, had begun to rot. A stroke in January 1947 allowed pneumonia to take hold, and before long his heart was failing.
A former staff writer for All That’s Interesting, Marco Margaritoff holds dual Bachelor's degrees from Pace University and a Master's in journalism from New York University. He has published work at People, VICE, Complex, and serves as a staff reporter at HuffPost.