Bootleggers, Bathtub Gin, & Speakeasies: Organized Crime in the 1920s

Mobsters and bootleggers ran rampant during the Roaring Twenties in an attempt to get rich off the Prohibition Era.

Dec 3, 2022By Amy Hayes, BA History w/ English minor
Organised Crime
Crowded bar enjoying drinks before the initial wartime Prohibition took effect at midnight on July 1, 1919, via Library of Congress, Washington DC; with photo of Charles ‘Lucky’ Luciano.


The Roaring Twenties was a decorative decade full of extravagant parties, events, entertainment, and consumerism. The economy was booming, and at the height of it all was Prohibition. The 18th Amendment was ratified in January 1919, which prohibited the manufacture, transport, and sale of liquor. Within the same year, the Volstead Act was passed to help enforce the new anti-liquor laws. The goal of Prohibition failed miserably, and it became a crime-filled fiasco. People still found a way to manufacture, distribute, and buy alcohol. Mobsters were at the forefront of the illegal business, which led the Roaring Twenties also to be known as the decade of organized crime.


The Temperance Movement Pushes for Prohibition in the Roaring Twenties

American Federation of Labor members gathered for a Prohibition demonstration courtesy of Herbert A. French, 1919, via Library of Congress, Washington DC


America had a huge alcohol problem for centuries leading up to the Roaring Twenties. From the time Puritans arrived in America in 1630 with beer and wine up through the 1700s, heavy drinking was common and troublesome among the colonies. The problem was so apparent that the British Parliament made a first attempt at prohibition in 1730. The plan failed in just 13 years as colonists found other ways to make and import liquor.


Organizations that encouraged the abstinence and the banning of alcohol began popping up in the 1800s. Some of the earliest organizations included the Massachusetts Society for the Suppression of Intemperance and the American Temperance Society. The push for prohibition by the temperance movement began to make progress. By 1851, Maine had become the first state to prohibit alcohol. This event encouraged other states to follow Maine’s lead within the next few years.


The ban on alcohol didn’t last much longer as the Civil War became a more apparent concern. Prohibition advocates turned their attention to supporting the abolishment of slavery, and the federal government needed more tax money to fund the war against the South. Once the war ended, the focus turned back to prohibition. A determined prohibitionist group called the Anti-Saloon League was established in 1893. The organization was led by Wayne Wheeler, who managed to convince Congress to push for a ban on alcohol. By 1917, decisions were being made about prohibition in the Senate and House of Representatives. Two years later, in 1919, the 18th Amendment was ratified and enforced by the Volstead Act. Prohibition was set to take effect on January 17, 1920.


Mobsters Take Over the Prohibition Era

Washington Times-Herald newspaper article talking about the struggles of Prohibition enforcement, 1922, via Library of Congress, Washington DC

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Many people were unsurprisingly dissatisfied with the banning of alcohol. People found other ways to make liquor and sell it. Bathtub gin was a homemade high-proof liquor made from fermented fruits and vegetables. Rotgut whiskey was made using industrial alcohol that contained harmful chemicals, which caused thousands of people to get sick or even die. Cocktails became popular in speakeasies to mask the poorly made liquor. Notorious gangsters across the nation jumped on the cash cow opportunity to manufacture and sell illegal wine and spirits. Beforehand, mobsters ran other racketeering businesses such as gambling, prostitution, and drug and weapon trafficking.


The Roaring Twenties quickly became a decade full of organized crime that caused chaos among communities where gangsters ruled all. New York and Chicago were two major cities where racketeering was a big business. Organized crime was not nearly as present as it became during the Prohibition era. Some say the Roaring Twenties was the birth of organized crime.


Gangsters rolled in loads of cash by manufacturing and selling alcohol to thousands of speakeasies spread across the cities. The bootlegging business got so big that it needed more structure. Mobsters hired accountants, brewers, lawyers, and rum-running boat captains. Bootleggers built an intricate system to control their operations, making it difficult for the FBI’s Bureau of Prohibition agents to take them down. Bribing policemen, witnesses, and even FBI agents was all a part of the business, and that was an expense that mobsters afforded in order to keep their racketeering businesses.


Notorious Crime Bosses & Bootleggers

Mugshot of New York Mafia boss Charles “Lucky” Luciano, via The Mob Museum, Las Vegas


George Remus was arguably the biggest bootlegger of Prohibition. Remus was a pharmacist before he attended law school to become a criminal defense attorney. He practiced for about 20 years before deciding to dabble in the illegal booze trade. As a criminal defense attorney, Remus had a significant advantage in knowing the law and finding loopholes in the Volstead Act. He conjured up a plan called “The Circle” to buy up as many distillery warehouses as he could. The warehouses still contained tons of liquor made before Prohibition. He established a trucking company to transport the liquor and opened his own drug company to distribute it, selling liquor for “medicinal purposes,” which was legal.


Remus was making tens of thousands of dollars a day. Bootleggers and rum runners were traveling to Remus’ hidden and strictly guarded whiskey distribution center in Ohio at all hours of the day. He had thousands of employees running his operation, and Remus made millions. He was eventually indicted for numerous Volstead Act violations in the mid-1920s and served two years in federal prison.


Charles “Lucky” Luciano was a notorious Italian gangster who found himself at the top of the New York Mafia boss chain. Born in Sicily, Luciano moved with his family to the Lower East Side of New York City at a young age. He became a member of the Five Points gang before mob boss Giuseppe Masseria hired him as a gunman. Luciano turned on Masseria by helping Masseria’s rival, Salvatore Maranzano, assassinate him.


Luciano gained control of the Genovese mob family and assumed racketeering operations in gambling, bootlegging, and prostitution. One of his most notable acts was the establishment of the Commission in the early 1930s, or the National Crime Syndicate. Luciano was one of the major mob bosses that defined modern organized crime.


Gangster Al Capone’s mugshot and criminal record identification card, via Federal Bureau of Investigation


Al Capone was the kingpin gangster of Chicago during Prohibition. He dropped out of sixth grade and was accepted into the Colosimo Chicago mob by street gang leader Johnny Torrio. Head mob boss Big Jim Colosimo was gunned down, presumably by Italian-American gangster Frankie Yale. Torrio was suspected of having ordered the hit, and he stepped up to take Colosimo’s place. Al Capone became Torrio’s right-hand man, and the Chicago Outfit gang rose in notoriety as it controlled the South Side. Five years after Capone joined Torrio in Chicago, Torrio was shot by crime boss and North Side gang rival George “Bugs” Moran. Torrio managed to survive but decided to retire and handed gang operations over to Al Capone in 1925.


Al Capone became one of the most successful racketeers in Chicago. He owned thousands of speakeasies. He led illegal brewery, distillery, and distribution operations and made tens of millions of dollars each year throughout Prohibition. Al Capone was responsible for ordering a hit on Bugs Moran’s men, who were machine-gunned down by men dressed in police officer uniforms. The event occurred on February 14, 1929, and was named the St. Valentine’s Day Massacre. The murders are considered the beginning of Capone’s downfall. He soon gained the nickname “Public Enemy No. 1” for wreaking havoc on Chicago communities due to gang violence.


Crowded bar enjoying drinks before the initial wartime Prohibition took effect at midnight on July 1, 1919, via Library of Congress, Washington DC


Law enforcement managed to put Capone in jail a number of times between 1929 and 1931 for small charges, such as carrying a concealed deadly weapon and failure to appear in court. In the meantime, the US Treasury Department was building up a case on Capone for tax evasion, which would eventually land him behind bars for seven and a half years. He was released almost four years early after fully paying all fines, which equaled about $4.5 million in today’s value. His health had significantly declined while in prison; Al Capone died in his Florida home almost eight years after his release in January 1947.


The End of Prohibition: Repealing the 18th Amendment

Crusaders member Elizabeth Thompson posing next to a “Repeal the 18th Amendment” tire cover by Underwood & Underwood, 1930, via Library of Congress, Washington DC


Prohibition didn’t stop people in the Roaring Twenties from consuming alcohol, and it may have encouraged drinking even more than beforehand. After a decade of the Bureau of Prohibition being unsuccessful in enforcing the 18th Amendment, “dry” Americans felt hopeless. Organized crime violently impacted uninvolved community residents, and gangsters and bootleggers were greedily out of control. The St. Valentine’s Day Massacre was really a wake-up call to the fact that the current Prohibition regulations weren’t being enforced, and that it was taking a major toll on the entire nation.


People were organizing repeal campaign groups, such as The Crusaders, to encourage repealing the 18th Amendment. When Herbert Hoover took office in 1929, he set up the Wickersham Commission to investigate why Prohibition wasn’t working. Investigators created several reports about Prohibition-related crimes and issues. The commission decided that the 18th Amendment shouldn’t be repealed because the heart of the issue was corruption and lack of enforcement of the regulations. Police officers, and even federal agents, were cutting deals and taking hefty bribes from mobsters.


The Great Depression encouraged many to switch sides and support the repeal. Franklin D. Roosevelt won the 1932 presidential election by a landslide, partially due to his pro-repeal campaign. By December 1933, Roosevelt announced the repeal of the 18th Amendment as the 21st Amendment was ratified. The nationwide Prohibition was officially over, but states were still allowed to make their own decisions on the matter.


Some states remained dry for years. Mississippi kept its Prohibition laws until 1966, making it the last state to lift the total ban on alcohol. Numerous counties within the Bible Belt states are still dry to this day. Some counties or states have strict laws to regulate the sale of alcohol, such as no alcohol sales on Sundays.


The Biggest Failure of the Roaring Twenties 

Crowded bar of people celebrating the repeal of the 18th Amendment and end of Prohibition, via The Mob Museum, Las Vegas


There was initially a large amount of support for Prohibition. Dry advocates hoped it would pull America out of the long, drunken state it had been in since alcohol first arrived. Most people didn’t expect that it would cause more harm than good. Organized crime emerged because of Prohibition, as it gave gangsters another racketeering operation. Mobsters made millions of dollars every year from bootlegging and running thousands of speakeasies. Police officers and federal agents turned a blind eye to those who were more than happy to pay them off.


By the end of the Roaring Twenties, it was clear that Prohibition needed either better regulation or to be ended altogether. The Great Depression really pushed Prohibition to its end in hopes that legalizing alcohol would revive the American economy. Alcohol sales tax did help with federal funding, but the nation didn’t see much financial relief as expected until World War II. Organized crime didn’t disappear, but the end of Prohibition eliminated one of the biggest racketeering operations of the time.

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By Amy HayesBA History w/ English minorAmy is a contributing writer with a passion for historical research and the written word. She holds a BA in history from Old Dominion University with a concentration in English. Amy grew up in the historic state of Virginia and quickly became fascinated by the intricate details of how people, places, and things came to be. She specializes in topics on American history, Ancient and Medieval England, law, and the environment.