Top 16 Most Famous Bootleggers In The 1920s

Last Updated: October 25th, 2023 by Kerry Wisby (Teacher-BA English Literature, 1920s & Great Gatsby Expert)

When you think of the bootlegging business in the roaring twenties, who comes to mind? Chances are that you think of Al Capone or maybe Dutch Schultz, but did you know that prohibition was so unpopular that thousands of people were actually making bathtub gin?

three gentlemen in suits drinking at a bar

Of course, this is the way history is made. No one wants to hear about the small-time, small-town, local guy who made some illegal liquor in a still behind his home and gave it out to family and friends.

We want to hear about the gangsters who made millions of dollars, drove the best cars, wore custom-made suits, and killed anyone who got in their way.

With that in mind, today’s article is about 16 of the most notorious bootleggers in the United States.

Not necessarily in order because trying to create determiners would be a nightmare, this is a random list of the worst offenders that topped the FBI’s most wanted list at one time or another.

Who Were the Top 16 Most Famous Bootleggers of the 1920s?

This list of the most famous bootleggers during the enforcement of prohibition laws were also some of the most successful gangsters of all time.

1. Arnold Rothstein: Often called “The Brain” because of his intelligence, Rothstein was a gambler, racketeer, and businessman. Rothstein was one of the most powerful figures in New York City during the Prohibition era. He was involved in a wide range of illegal activities, including bootlegging, gambling, and prostitution. He was also suspected of fixing the 1919 World Series.

Arnold Rothstein wearing a suit and a fedora in Chicago 1919
A picture taken in 1919 of Jazz Age racketeer Arnold Rothstein by Chicago Daily News

2. Al Capone: Perhaps THE most famous gangster of all time. Capone was the head of the Chicago Outfit, one of the most powerful crime syndicates in the country. He made millions of dollars from bootlegging, gambling, and prostitution. Capone was eventually convicted of tax evasion and sent to prison. He died of a stroke, cardiac arrest, and pneumonia at the age of 48. Prior to his death, he was diagnosed with advanced syphilis, which led to dementia.

a 1930 file photo of Al Capone wearing a suit with a pocket watch
Al Capone in 1930 by Chicago Bureau

3. Dutch Schultz: Born Arthur Simon Flegenheimer in the Bronx, New York, he started out as a burglar and then turned bootlegger during Prohibition. He eventually became one of the most powerful gangsters in New York City, controlling a vast criminal empire that included bootlegging, gambling, and prostitution. Schultz was a ruthless and violent man who was known for his temper and willingness to kill. He was also a master of political corruption, and he used his influence to protect himself from prosecution. In 1935, Schultz was assassinated by a group of mobsters who were working for Lucky Luciano.

Mugshot of Dutch Schultz
Mugshot of Dutch Schultz, 1930 by New York Police Department

4. Charles “Lucky” Luciano: He was one of the most influential mobsters in American history. Luciano was a key figure in the unification of the Italian-American Mafia and the establishment of the Commission, the governing body of organized crime in the United States. He also made a fortune from bootlegging during Prohibition and was known for killing his rivals, such as Dutch Schultz.

Charles Lucky Luciano sitting and sipping wine
Italian mobster Charlie “Lucky” Luciano by Remo Nassi

5. Sherman Billingsley: A former bootlegger who became a successful nightclub owner. Billingsley owned New York’s famous Stork Club, a popular hangout for celebrities and gangsters. He was also a close associate of Luciano and Costello.

Sherman Billingsley holding a cigarette and smiling at the camera
Photo of Sherman Billingsley at his Stork Club, 1951 by Liggett & Myers

6. William McCoy: Boatbuilder and navigator of seagoing vessels, McCoy decided to give bootleg rum a try to boost his income. Unlike other gangsters, McCoy was against violence, and although he carried a huge machine gun, he only fired warning shots. He did go to prison for bootlegging, but afterward, he lived off the millions he had made and never returned to a life of crime.

William McCoy wearing a white shirt and a fedora hat
Rumrunner Captain William S.(Bill) McCoy, 1921 by Outlanderssc

7. Enoch Johnson: Enoch Johnson, also known as “Nucky” Johnson, was a political boss and racketeer in Atlantic City, New Jersey during the Prohibition era. He was not a bootlegger himself but was involved in the bootlegging trade through his political connections. He was also involved in other illegal activities, such as gambling and prostitution.

8. Lee Petty: If you’re wondering if there is any relation to the Pettys of NASCAR fame, yes, there is. Whether Lee Petty actually made bootleg liquor or was simply a distributor, Petty was know for being an expert at outrunning the law while driving. He later used these driving skills to become one of the founders of NASCAR racing, probably with the money he earned running liquor sales.

9. George Remus: The “King of the Bootleggers”. Remus was a former lawyer who turned to bootlegging after Prohibition was enacted. He amassed a huge fortune by buying up pre-Prohibition liquor and selling it illegally. He was eventually caught and sent to prison, but his story is one of the most fascinating of the Prohibition era. In fact, his story is such a hoot that I will be writing an article about this bootlegger in the near future.

George Remus
George Remus by jp_stl_mo

10. Johnny Torrio: Al Capone’s predecessor and mentor, he was head of the Chicago Outfit. Torrio was a brilliant strategist who helped build the Outfit into a powerful criminal organization. He was also responsible for importing large quantities of liquor from Canada during Prohibition.

photo of John Torrio wearing a suit and hat
John Torrio, 1939 by Unknown author

11. George “Bugs” Moran: A top lieutenant in the Masseria crime family. Moran was a fierce rival of Capone, and he was involved in the St. Valentine’s Day Massacre in 1929. Moran was eventually killed by Capone’s men in 1946.

a sketch of George Bugs Moran
George Bugs Moran by Dane Nicklas

12. Dean O’Banion: He was one of the most powerful bootleggers in Chicago during Prohibition, and he controlled a large network of distilleries, breweries, and speakeasies. He was also involved in other illegal activities, such as gambling and prostitution. O’Banion’s bootlegging operation was very lucrative, and he amassed a large fortune. He used his money to buy a flower shop on North State Street in Chicago, which he used as a front for his criminal activities. O’Banion was also a flamboyant dresser, and he was known for his expensive suits and hats.

Dean O'Banion wearing a white dress shirt and dark suit
Dean O’Banion on his wedding day by Unknown author

13. Jack “Legs” Diamond: Known as Gentleman Jack or “Legs”, He started out as a petty criminal but eventually rose to become one of the most powerful bootleggers in New York City. He was known for his ruthlessness and ability to escape from law enforcement. Diamond was also known for his flamboyant lifestyle. He was a womanizer and a gambler, and he loved to spend money on expensive clothes and cars. He was also a talented dancer and known for his ability to hold his liquor. Diamond’s bootlegging operation was very lucrative, and he amassed a large fortune. He used his money to buy a luxurious apartment in Manhattan, and he also owned a number of speakeasies.

Jack Legs Diamond wearing a dark gray overcoat and fedora hat
Jack “Legs” Diamond in 1931 by Unknown author

14. Meyer Lansky: Born in Russia, Lansky immigrated to the US in 1911. Lansky started out as a small-time gangster but quickly rose through the ranks of the criminal underworld. He was a close associate of Charles “Lucky” Luciano, and together they formed the National Crime Syndicate, a powerful criminal organization that controlled organized crime in the United States. Lansky was also involved in bootlegging during Prohibition. He was a key figure in the Bugs and Meyer Mob, which was one of the most powerful bootlegging gangs in New York City. The gang smuggled liquor from Canada and the Caribbean, and they also ran a number of speakeasies. Lansky was a shrewd businessman, and he made a fortune from bootlegging. He was also a master of political corruption, and he used his influence to protect himself from prosecution.

Meyer Lansky's photograph taken in 1958
Meyer Lansky’s photograph taken in 1958 by Acratopotes

15. Bugsy Siegel: Born Benjamin Siegel, “Bugsy” started off as a small-time criminal but quickly became one of the biggest bootleggers of all time. Bugsy was known for forming a group called Murder, Inc. No, they weren’t actually incorporated, but this was the name Bugsy called the group of hitmen who were at his beck and call. After stealing cash meant for the Flamingo Hotel and Casino, he was assassinated in 1947.

mugshot of mobster Benjamin Bugsy Siegel
Mugshot of Jewish-American mobster Benjamin “Bugsy” Siegel in the 1920s by New York Police Department

16. Joseph P. Kennedy: If you are wondering about this name as well, yes, the infamous Kennedys of today are related to Joseph P. Kennedy. While there is no proof that this man made or sold bootleg alcohol, it’s rumored that Kennedy did make money from prohibition. This Kennedy apparently preferred to make his money from stock manipulation and insider trading.

There are plenty of other bootleggers and rum runners who were famous in their time, including Wayne Wheeler, Roy Olmstead, the Bondurant brothers of Virginia, and many others.

What Is the Name of the Most Famous Bootlegger During Prohibition?

Al Capone's photo printed in a newspaper

Hands down this would have to be Al Capone.

I’m not sure why he is more infamous than George Remus, who has a more interesting tale to tell in my opinion. However, there are dozens of movies and books about Al Capone, and only one movie that I’m aware of about the life of George Remus.

Perhaps it’s because he orchestrated the St. Valentine’s Day massacre. Perhaps it’s because of his flamboyant personality.

I honestly think it’s because he loved publicity. While other mobsters tried to stay out of the limelight, Capone loved the press, and they loved him in return.

Some of his most famous quotes are known by just about every American, including:

  • You can get farther with a kind word and a gun than just a kind word.
  • All I ever did was supply a demand.
  • I’m not a murderer. I’m an American businessman.
  • Prohibition is a business. Just like any other business, you have to protect your interests.

Quotes such as these sold newspapers and made Al Capone a household name, especially during the period when the National Prohibition Act was in place.

What Are Two Facts That Apply to All Bootleggers of the 1920s?

While bootleggers were in every town and every big city, they weren’t as different as one might think.

Port wine Boats

Two facts that applied to all bootleggers in every part of the country are:

1. Bootlegging was a very lucrative business. Bootleggers could make a fortune by selling illegal alcohol. In fact, some bootleggers became very wealthy during Prohibition.

2. Bootleggers were often involved in violence. The illegal nature of bootlegging made it a very dangerous business. Bootleggers often had to use violence to protect their turf and their profits.

Bootlegging may have seemed harmless, but it actually led to the rise of organized crime and became the basis for modern organized crime families today.

Why Weren’t More Bootleggers Prosecuted?

The overwhelming majority of Americans saw liquor as a harmless vice. I’m betting that many people knew friends and family members who were selling liquor, but they weren’t going to turn in their own family, were they?

A good bootlegger would also look after his community and the women in their lives. If they made a small fortune on their illegal activities, they would share that money with widows who may have lost their rum-running husbands, or they might pay to build the town a new church. Americans have always had a love-hate relationship with modern-day Robin Hoods.

Last, bootleggers often bribed law enforcement officials or even judges to avoid getting caught or to evade the law. This made it difficult for the government to crack down on bootlegging.

While we may think of bribes as something that doesn’t happen today, back 100 years ago, many people stayed out of jail or got out early by bribing judges and even juries.

Who Was the Most Famous Moonshiner of the 1920s?

Three men wearing retro gangster attire at a club drinking alcohol

I suppose we should consider that not everyone was making rum or gin back in the day. Gin was easy to make and could be mixed up in a large container (most people used their bathtub).

Moonshine is a bit different even though it is still alcohol. Frequently referred to as White Lightening or Hooch, it’s made from fermented corn or wheat mash and requires oak barrels for aging.

The most famous moonshiner of all time would have to be the Bondurant brothers of Virginia. There were crooked officials in Franklin County, and the Bondurant boys thought they would put a stop to that.

This is kind of like the pot calling the kettle black. Both were doing illegal dealings, but in their favor, the Bondurant boys weren’t government officials.

This feud between the government and the Bondurant family ended up costing several lives and lots of bloodshed.

The grandson of one of the original Bondurant moonshiners wrote a book about their lives and is now considering making his own bourbon-style whiskey.

Before You Go ….

There were so many bootleggers during prohibition that it can be hard to keep them all straight.

Some were known only on the East Coast, others were famous in the Pacific Northwest, but all were famous for avoiding the federal government, making millions of dollars, and ruling their empires with violence.

Prohibition created a golden age of organized crime, if you will, and bootleggers were some of the most powerful and influential figures in the criminal underworld.  If you enjoyed this article you might also like to head over to our gangster section were we have a lot more articles to read – Click Here to see more!

Top 16 Most Famous Bootleggers In The 1920s
Top 16 Most Famous Bootleggers In The 1920s
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