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15 Fascinating Photos of Historical Gangsters

OMG November 29, 2016 By Vincent

You don't hear a lot about gangsters these days. Perhaps it is because of increased policing efforts and improved methods at breaking up organized crime or maybe it is because they are more inclined to keep a low profile and are better at avoiding gaining too much attention. Whatever the case may be, it certainly seems that there was once a time where gangsters were more prevalent.


In a period of history where circumstances led to the rise and proliferation of organized criminals, they were all over the newspapers and media of the day. Here we look at some historical photographs of these gangsters and tell the stories behind them.

1. Girl Bandits

Police officers are shown here questioning a pair of female crooks who were dubbed 'the girl bandits' after a series of home robberies that they had managed to escape from. Jean Buttick, 15, and Anna Varich, 16, were caught red-handed looting a bungalow at 6152 S. California Avenue on March 20, 1927.


The Chicago Tribune reported at the time: "In the kitchen, as they seized her [Anna] she spilled rings, bracelets, beaded bags, and what not from every part of her clothes. When they shook her she literally dripped booty." 

2. Three Fingered Jack

The Mobster knows as "Three-Fingered Jack" was actually named Jack White and by 1925 he had been charged twice for the murder of a police officer. Hiding his face from the photographers as he is escorted to court, amazingly, Jack managed to avoid a jail sentence due to the excellence of his lawyer.


With less forensic techniques and technology at their disposal, gaining evidence for a conviction was much harder back then.

3. The Notorious Jon Dillinger

Jon Dillinger is one of the most infamous names in the history of American gangsters after he orchestrated several armed robberies, being accused of robbing 24 banks and four police stations, among other activities. Here, he is pictured at the preliminary hearing of a murder case, his only homicide charge despite his various robberies as he received a bullet to the chest, where he was wearing bulletproof armor, and returned fire.


Dillinger went to prison twice but escaped twice and when he was cornered leaving a movie theater, he was eventually shot in the street.Handcuffed to Dillinger (who is on the right) is  R.M. Pierce, the deputy sheriff tasked with making sure he didn't run away.

4. Heading To Court

Here Dillinger is pictured heading to court for the robbery of the First National Bank, the picture being taken in  Chicago, Illinois. Looking relatively unfazed, perhaps Dillinger is well aware that, even if he does get sent down, he will escape.Dillinger was noted as a sort of Robin Hood figure as he never harmed any civilians in his robberies.


Dillinger became the most notorious criminal of the age and led to FBI reforms and a platform for J.Edgar Hoover to run for leader of the bureau on.

5. The Trial of Al Capone

Another notorious mobster, Al Capone made his money from bootlegging which was at a time when the U.S government enforced prohibition which made alcohol illegal. He would sell booze to underground nightclubs and bars. With fierce competition, Capone was accused of racketeering and orchestrated massacres of his rivals but was never convicted of any of these charges.


It was his eventual sentence for tax evasion that brought an end to his criminal reign. He would later die of complications brought on by syphilis.

6. The St. Valentine's Day Massacre

Assumed to be the handiwork of Al Capone in an attempt to eliminate rival mobster Bugs Moran, Mobsters rented an apartment across from a trucking warehouse run by Moran's North Side Gang where they then performed a faux raid dressed as police officers. Lining up the mobsters to no resistance, the fake officers then gunned down their competition.



Here, investigators are trying to gather evidence about the guns used so they can identify who bought them and when and where they were sold.

7. Capone Leaves Court

During his trial, Al Capone would be escorted away from the courthouse surrounded by swathes of police officers. This was mostly for his own protection as he was so notorious and the crimes he'd instigated so violent that he was wanted dead by many other crime bosses and those fearing he may testify against them.


Known for his luxury clothes, flashy jewellery and big persona, it was widely thought that it was partially down to his profile that led the police to come for Capone. The photo was taken December 10, 1931.

8. Prohibition

With the government enforcing prohibition, gangsters like Al Capone and Bugs Moran made money out of selling illegal alcohol which meant authorities did their best to stop shipments coming into towns and cities with it often traveling from over the border in Canada. Here officers investigate an illegal shipment which they've stopped.


Hidden inside the barrels are smaller bottles of alcohol.

9. Clarence Darrow

Clarence Darrow was an America lawyer,  a leading member of the American Civil Liberties Union, and prominent advocate for Georgist economic reform but he made a name for himself defending gangsters and crooks in court. His most notable case was defending Richard Loen and Nathan Leopoldo Jr. The pair were dubbed with the nick name “thrill killers”


Just 18 and 19 at the time, Darrow successfully got them off of a death sentence although they did receive life plus 99 years for their crimes.

10. Mugshot

A famous mugshot of Al Capone in his characteristic pork-pie hat, the gangster was jailed several times but only ever sent to prison once for his tax evasion. One of the most infamous mobsters of all time, films have been made about his exploits and books written about them too.


Sent to the infamous island prison of Alcatraz, Capone was a target for much abuse whilst incarcerated and was even stabbed.

11. Walter Smith

Even for a mobster, Walter Smith was notorious and this was because of his cold-blooded and ruthless nature that led him to shoot people in broad daylight. A criminal in Australia, Smith was listed as ‘charged with breaking and entering the dwelling-house of Edward Mulligan and stealing blinds with a value 20 pounds (part recovered)’, and with ‘stealing clothing, a value of 26 pounds (recovered) in the dwelling-house of Ernest Leslie Mortimer.’


The photo was taken on 24 December 1924.

12. William Moore

Another Australian criminal, showing that it was not just America that had problems with gangsters, William Moore was an opium dealer and trafficker who was notorious for his dockside trade where he would associate with thieves and dog traders. Selling so much product, large quantities of it turned out to be fake.


A very intimidating character, few complained about the quality of his product.

13. George “Bugs” Moran

Al Capone's biggest rival and the man thought to be the target of the Valentine's Day Massacre, Moran ran the Irish gang the North Side Gang who would regularly fight with Al Capone's Italian gang, The Chicago Outfit. Eventually, Moran would lose power from his gang and go from being one of the richest men in Chicago to almost penniless in around 17 years.


Moran went to jail for fraud and robbery and ended up dying in prison.

14. The High Life

At the height of his criminal powers, Capone may well have been the richest man in Chicago and here he can be sitting fishing whilst lounging on the top deck of his yacht. Known for enjoying fine clothes and high-end cigars, Capone lost much of it when convicted of tax evasion but was still a wealthy man when he left prison.


After he was free again, it was found, due to untreated Syphilis, he had the mental capacity of a 12-year-old and he died shortly afterward.

15. Frank Nitti

Al Capone's number 2 and right-hand man, Nitti was in charge of all strong-arm and 'muscle' operations in Al Capone's Chicago Outfit and succeeded him as its boss when Capone was sent to prison. Nitti was also sentenced to tax evasion at the same time as Capone but only received an 18-month sentence as opposed to the 11 years Capone was given.


Nitti developed severe claustrophobia due to his first prison stint so when indicted on extortion charges where he would have to spend a second time in jail, he took his own life.

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