Secret Lives of Famous Gangsters in the 1920s: Guns, Booze & Glamour

Last Updated: October 24th, 2023 by Kerry Wisby (Teacher-BA English Literature, 1920s & Great Gatsby Expert)

Famous Gangsters in the 1920's

The 1920s were exciting times for most Americans. Prohibition was in full effect, but that didn’t stop people from drinking and dancing the night away.

The depression would hit at the end of this decade, but earlier in the 1920s, no one knew it was coming. The war was over, everyone seemed to have plenty of money, and fashions were showing more skin than anyone ever dreamed possible.

Secret Lives of Famous Gangsters in the 1920s

While it seemed as though new millionaires were cropping up everywhere, it was mostly the criminal gangs and bootleggers who were raking in the big bucks.

Ordinary, law abiding people were left out in the cold, money-wise. Most began to wonder if they should take up selling illegal beer or illegal booze and robbing banks.

Well Known American 1920’s Gangsters

The prohibition era also brought in a wave of new gangsters that Americans weren’t quite ready to deal with. Some, like Bonnie and Clyde and Al Capone, were idolized by the press. Others, such as John Dillinger and Pretty Boy Floyd, were demonized.

One thing that all these gangsters had in common was that they had secrets they hoped no one would ever discover.

Keep reading to find out what a life in illegal gambling, illegal alcohol sales, and organized crime was really like for gangsters of the 1920s.

Al Capone

Al Capone in 1930
Al Capone in 1930 by Chicago Bureau

One of the most famous gangsters of this time was Al Capone. To this day, everyone over the age of 10 knows this gangsters name.

Al Capone was 21 years old when the Volstead Act, which outlawed the manufacture and sale of alcoholic beverages, was made law.

Capone very quickly became not only the most infamous gangster of his era but was even featured on the cover of Time magazine!

Born in New York in 1899, Capone had a short, stocky body and large, powerful hands that earned him a well-deserved reputation as a thug.

One look at Capone’s face and one quickly sees that his nickname “scar face” was accurate. Capone would sport three large scars on the left side of his face.

Capone’s secret? How he received those scars.

Before he became a famous gangster, Capone worked as a bouncer at a place called The Harvard Inn. This was a brothel where some truly hardened criminals were known to hang out.

Capone made the mistake of saying something ugly about a female client. The woman’s brother, Frank Gallucho, was the head of a local mafia gang.

Overhearing what Capone said, he pulled a knife and slashed Capone three times across the face.

Capone spent the rest of his life trying to hide those scars with makeup and talcum powder, and he frequently lied about how he got those scars.  Read more on how Al Capone died, his wife  or children here.

Legs Diamond

Legs Diamond court appearance
Jack “Legs” Diamond court appearance by Unknown author

Legs Diamond, whose real name was John Thomas Diamond, grew up on the streets of Philadelphia.

Very few people know how he got his nickname.

As a child, Diamond was accustomed to seeing push carts or horse-driven carts in his neighborhood. These carts were the way vendors sold goods when they did not have a store front. Everything from fruits and vegetables to cloth, coal, even ice was sold from these wooden carts.

Legs Diamond learned that children were not paid much attention to unless they were causing trouble. Some of Legs’ friends would distract the driver of the cart to give Legs time to steal whatever he could get.

Legs Diamond was the fastest runner in his neighborhood, which is how he earned his nickname.

You might know Legs by another nickname he earned later in life: The Clay Pigeon.

Clay Pigeons are used for shooting practice. Legs, or The Clay Pigeon, as an adult, had been shot at so many times and had numerous pieces of lead bullets left in his body that he earned this moniker in his later years.

Dutch Schultz

Dutch Schultz on 1935
Mugshot of Dutch Schultz by New York Police Department

Born in the Bronx, New York, in 1902, Schultz’s real name is Arthur Flegenheimer, and he literally “stole” the name Dutch Schultz. The real Dutch Schultz was a legendary gangster from about 100 years earlier!

Schultz opened speakeasies, imported Canadian whiskey, and was known to be an easy-going guy who would laugh at most insults.

His weakness? Schultz was a penny-pincher and watched every dime. You could insult Schultz to his face and he would laugh, but steal a dollar out of the cash drawer and he would shoot you dead on the spot.

Shultz and Legs Diamond were rivals, and their gang fare was legendary.

What most people don’t know is that even Schultz and Diamond got sick of all the bloodshed. They met secretly in a hotel to reach a ceasefire.

Diamond told Schultz that he would sell him a large speakeasy that Diamond owned but was in Schultz’s territory for half a million dollars. Schultz agreed and paid Diamond on the spot.

Diamond had men waiting outside the hotel, and when Schultz left the building, Diamond’s men tried to assassinate him.

They failed, but it did cause Legs Diamond to move his operations to upstate New York in hopes of preventing revenge by Schultz’s men.

It didn’t work. Diamond was murdered as he left a boarding house by what is assumed to be hitmen hired by Schultz.

Machine Gun Kelly

Machine Gun Kelly mugshot on 1930's
Mug shots, Machine Gun Kelly by Unknown author

Before the current hip-hop singer took this name, there was an infamous gangster who went by Machine Gun Kelly.

Born in 1897, Kelly was born into poverty and grew up near Memphis, Tennessee. Kelly is perhaps best known for frequently telling people that “No copper (slang for the police) will ever take me alive.”

What was Machine Gun Kelly’s secret? Unlike many other gangsters of his time, he didn’t start off his criminal life until he got married.

That’s right. Machine Gun Kelly was as harmless as a kitten until he met and married Katherine Shannon. She gave Kelly a wedding gift—a machine gun—the same one that would make him famous!

Katherine taught her husband how to use the gun and insisted that he not only practice with it but also later told him he could use that machine gun to run a bootlegging operation.

Machine Gun Kelly’s wife would even collect the spent shells from the gun and later pass them around as souvenirs!

Pretty Boy Floyd

Pretty Boy Floyd on 1920's
A crop of Pretty Boy Floyd’s mugshot by FBI

Born in poverty in the dust bowl of Central America, Charles Arthur Floyd worked hard in squatter’s fields.

Floyd dreamed of a better, easier life, so he robbed a small bank. He was caught and served a few years in prison.

Floyd’s secret is how he earned that moniker.

Fresh out of prison, Floyd had not changed his mind about wanting an easier way of life. He was going to meet with some local gangsters in Kansas City to talk about working together with them.

They decided to meet at a brothel. The madam of the brothel is said to have taken one look at Floyd and asked him not to join the gang. When the gang leader asked her why, she looked at Floyd and said “I want that pretty boy for myself!”

That was all it took. Every gangster in the state began to call Charles Arthur Floyd “Pretty Boy Floyd”.

Pretty Boy Floyd should have been dubbed Robin Hood. He was known to rob banks and take a few extra minutes to look for mortgage paperwork and burn it or rip it up in hopes that homeowners would be free from mortgage debt.

John Dillinger

Notorious gangster John Dillinger
Mug shot of John Dillinger by FBI

Like most of the gangsters of his time, John Dillinger was born into poverty. He grew up on his father’s farm in Indiana.

Poor as they were, Dillinger’s parents doted on their son. By the time he was 10, people described Dillinger as a “spoiled brat.”

Dillinger’s secret is how he created his gang.

Dillinger was out on bail and was awaiting trial for robbing a bank. While he had been in prison, he befriended four fellow inmates.

Dillinger smuggled guns into the prison, helping his four friends escape. Suspecting that Dillinger had been the one to smuggle the weapons, the authorities revoked his bail and arrested him again and held him in the county jail.

The four inmates who had escaped decided to return the favor. Five days after escaping, the quartet murdered the sheriff and freed Dillinger.

This gang of newly “released” prisoners robbed two banks and killed another police officer in the next 10 days.

The five gang members were caught in Phoenix, Arizona. Dillinger would later escape from prison yet again, even stealing the sheriff’s car to make his getaway.

These are just a few of the secrets of the well-known gangsters from the Jazz Age.

Who Was the Best Known Gangster of the 1920s?

It would have to be Al Capone.

Although there were a great many movies made about or based on other gangsters, it’s Al Capone that most people remember.

There were also movies about this infamous gangster, including 1987 classic The Untouchables, which stars Kevin Costner as Treasury officer Elliot Ness and Robert De Niro as Al Capone.

It’s interesting to note that Capone is not only the best-known gangster, he was also the richest. By controlling all the illegal gambling, prostitution, and the illegal production of alcohol, the Capone empire brought in an astounding $100 million yearly at the peak of its operation.

The best- known and richest mobster of the era was sent to prison on tax evasion charges, spending 7.5 years behind bars. He died at home due to complications from untreated syphilis.

Who Was the Smartest Gangster of the 1920s?

Smartest Gangster Johnny Torrio
John Torrio leaving the federal court house in New York during his trial by Unknown author

While people may have different opinions, we would have to say that the smartest gangster from this era would be Johnny Torrio.

Born in 1882, Torrio ran the city of Chicago and trained the man who would take his place—Al Capone.

Torrio was nicknamed “The Fox” and “The Brain” because of his cunning and sly moves. Even Treasury Officer Elmer Irey once wrote that, “He was the smartest and, I dare say, the best of all the hoodlums. ‘Best’ referring to talent, not morals.”

In January 1925, Al Capone was ambushed, leaving him shaken but unhurt.

Just twelve days later, Torrio and his wife Anna were ambushed outside their home. Torrio was shot several times and nearly killed. After recovering, he effectively resigned from Chicago mob life and handed control of the gang to Capone, and fled to New York City.

Who Was the First Gangster of the 1920s?

First Gangster of the 1920s
Charles Lucky Luciano (Excelsior Hotel, Rome) by Remo Nassi

Probably Lucky Luciano.

Born in Italy in 1897, Salvatore Lucania operated the Five Points Gang and is considered by many to be the father of modern organized crime in the US.

After winning a card game at 14, Lucania earned the nickname Lucky Luciano. He decided to drop out of school and earn his money protecting Jewish kids from the Italian and Irish gangs for ten cents a week.

Final Thoughts on Gangster From the 1920s

Even today, the infamous gangsters of the 1920s (and the 1930s) hold a certain fascination with the American public.

Though the public understands that these were blood thirty criminals who dealt in drug trafficking, bootleg alcohol, and the murder of both civilians and police officers, it seems that the allure of the gangsters during the prohibition era hasn’t died down yet.

Secret Lives of Famous Gangsters in the 1920s: Guns, Booze & Glamour
Secret Lives of Famous Gangsters in the 1920s: Guns, Booze & Glamour
You know about Pretty Boy Floyd, Dutch Schultz, John Dillinger, and Al Capone, but did you know about their secret lives? Find out what these gangsters from the 1920s thought no one would know about.
Gatsby Flapper Girl