Buzz
When the U.S. government aligned itself with the Temperance Movement and embarked on the ill-fated Prohibition experiment, it triggered an odd chapter in American history where the criminal underground found themselves becoming oddly famous—particularly the bootleggers, rumrunners, and moonshiners. These unlikely figures became the unsung heroes of Prohibition, quenching the country’s thirst despite the ban, and their exploits have led to some captivating stories.
10. Roy Olmstead
Roy Olmstead had been with the Seattle police for nine years before Washington state went dry, so by the time he and his partners started raiding bootleggers, he was already well-acquainted with the city. He also noticed something troubling about the busts—they were sloppy, careless, and missed so many obvious details that could have made their efforts far more effective. It didn’t take long before he concluded he could do better and began running his own bootlegging operation on the side. With alcohol still legal in Canada, Olmstead purchased liquor there and smuggled it south into the U.S.
Apparently, running the operation wasn’t as easy as it seemed, because he was soon caught, fined $500, and kicked off the police force. But Olmstead wasn’t the type to give up. He turned his side hustle into a full-time venture, rapidly growing to control the largest bootlegging empire in Seattle. He became one of the region’s top employers, earning about $200,000 a month. With his newfound wealth, Olmstead mingled with the city’s elite, purchasing a mansion for himself and his wife. His wife even ran a nightly children’s bedtime radio show from their home.
However, their extravagant lifestyle was short-lived. In 1924, their mansion was raided, and much of the conviction relied on illegal wiretap recordings collected by law enforcement. Olmstead, who was aware of the wiretapping and its illegality, believed the evidence wouldn’t be admissible in court. Yet the judge allowed it, and the Supreme Court upheld the decision. Olmstead was sentenced to four years in prison but was later pardoned by Franklin Roosevelt.
9. Fort Whoop-Up
In the 1860s, the American West was still a frontier for rugged hunters, trappers, and gold prospectors. It was illegal for them to trade their goods for Canadian whiskey, so they traveled north to the source of the liquor itself—Alberta—and established a trading post with what might be the most iconic name for such a place: Fort Whoop-Up. This trading hub became infamous as the go-to spot to exchange furs and hides for whiskey, making many people quite rich.
Trouble began when the fort’s popularity soared, leading to its expansion and a dangerous mix of people and interests. Alongside furs and alcohol, firearms became common, and tensions between white traders and nearby Native American tribes escalated. When American traders introduced smallpox, the disease spread rapidly through the Cree and Blackfoot tribes, deepening the conflict. Seeing the growing instability, the Canadian government took action, sending 300 Canadian Mounties to end the illegal trading and establish a firm military presence to prevent traders from relocating and continuing their operations elsewhere.
8. Pharmaceutical Chains
During Prohibition, drugstores and pharmacy chains sprang up across the country. The reason was simple—they became a highly profitable business. Not all alcohol was banned. It was still permissible to distill and sell whiskey, but only for medicinal use. These medicinal bottles had to have a prescription attached—likely from a doctor—be labeled with 'Bottled-In-Bond,' and contain whiskey at 100 proof.
Prescriptions could be refilled every 10 days, and the legal sale of whiskey through pharmacies provided the perfect front for bootleggers. F. Scott Fitzgerald even alluded to this practice in *The Great Gatsby*, where Gatsby’s wealth came from a chain of drugstores, a clear reference to his bootlegging business.
Curiously, by this point, the American Medical Association had already stated that alcohol was not a recommended treatment for any condition. However, this minor detail was ignored by the legislature enforcing Prohibition, resulting in a large number of whiskey bottles being sold with labels claiming they were 'Unexcelled for Medicinal Purposes.' Most prescriptions, for those who even bothered, noted that the whiskey was intended for use in an 'Emergency.'
Some of the drugstore chains that experienced incredible growth during Prohibition are still thriving today. Walgreens, for example, saw a dramatic increase in stores during this time, though the official narrative claims this was due to the rising popularity of their newly introduced milkshakes.
7. Jennie Justo
Jennie Justo was one of the few women to earn the title of 'Queen of the Bootleggers,' but this label didn't define her after Prohibition came to an end. Her real name was Vinzenza DiGilormo, and she followed her family’s tradition of living outside the law. Her father had been killed, allegedly as revenge for her brother’s betrayal of his bank heist partners. Afterward, it was up to Jennie to take care of her younger siblings, since her mother and other brothers had also clashed with law enforcement.
Unlike many bootleggers, Jennie earned a reputation for running respectable speakeasies and serving high-class clients. She took pride in keeping things professional, especially since her speakeasy operated out of her own home. However, it didn’t take long before she became a target for law enforcement. Rumors spread that she had rejected a federal agent’s romantic advance, and after that, she found herself constantly under scrutiny.
Eventually, she was arrested and spent six months in jail. Upon her release, loyal customers greeted her with flowers and even organized a small parade back to the speakeasy. She was quickly arrested again, though her landlord took the fall for her. It all came to naught, as she was jailed for a probation violation. She was freed after Prohibition was repealed and later married Chicago Bears quarterback Arthur Bramhall. Together, they opened a legal bar that started a new chapter in their lives.
6. Rum Row
With alcohol prohibited in the United States, bootleggers turned to the seas to continue their trade, leading to the establishment of Rum Row. Since the U.S. government had no jurisdiction over waters about 5 kilometers (3 miles) offshore, rumrunners could dock their ships just outside this zone, allowing them to freely operate. They imported rum from the Caribbean and liquor from Europe, and as long as they stayed beyond the 3-mile limit, they were immune to prosecution.
In response to the challenge, the government acted in 1924, extending its control to waters up to 19 kilometers (12 miles) from the coast. This new regulation made it significantly harder for bootleggers to continue their operations on the high seas.
The ships of Rum Row were stocked to satisfy thirsty customers, making them tempting targets for pirates. While the boat operators were armed, they couldn't prevent theft. One notorious incident involved a French ship being raided for $800,000 worth of liquor over 10 days. Other vessels were found abandoned and stripped, with no crew left aboard.
A clever group of pirates once disguised their ship as a Coast Guard vessel, successfully boarding rumrunners while posing as U.S. military personnel. The rumrunner ships, however, were highly susceptible to disaster, as the waters they frequented were often shrouded in thick fog and plagued by unpredictable waves. This led to many vessels wrecking along the shores of New York and New Jersey.
5. America’s Small-Time Female Bootleggers
The illicit alcohol trade wasn't just dominated by men. Across the United States, many women played a significant role in bootlegging, particularly in the western regions. In these more remote areas, where homes were scattered far apart, it was harder for authorities to track who was operating stills in their kitchens or backyards. These women often supplied local bars and speakeasies, making a comfortable living off their craft.
A woman known as 'Birdie' Brown, originally from Missouri, settled in Montana on a 25-acre homestead. With a large log cabin, fields of crops, livestock, and a fully enclosed property, she created a lifestyle that was funded by her home-brewed alcohol, which was famous in the area for being the best in the country. Sadly, her story ended in tragedy when her still exploded, costing her life.
While many female bootleggers operated on a much smaller scale than infamous figures like Al Capone, their creativity was no less impressive. Mary Ann Moriarty ran a laundry service, enlisting her daughter to deliver freshly cleaned clothes along with flasks tucked into the bundles, charging $2 per gallon. Meanwhile, former dance hall girl Josephine Doody catered to railroad workers, signaling the number of gallons they wanted by blowing the train horn once per gallon when it arrived in town.
Women in the bootlegging world often had the advantage of being treated more leniently by male law enforcement and judges, who were softer on them than their male counterparts. Gray-haired matron Kate Farlan and 80-year-old Lavinia Gilman were given special treatment due to their age and gender, even though Gilman had been caught running a 300-gallon still.
4. The Bondurant Boys
By sheer chance, Jack Bondurant’s grandson would grow up to write a novel about his grandfather that was eventually adapted into the film Lawless. Although the movie took certain liberties with the story, the tale of the three brothers from Virginia was already legendary. Jack’s son, intrigued by his family’s past, dug into genealogical records and uncovered a different side of the Bondurant brothers—one that went far beyond the quiet image of a gruff farmer raising cattle in Virginia, revealing court records and newspaper articles that told a much more colorful story.
During the 1930s in Virginia, moonshine flowed freely, and much of it was transported in the back of a Bondurant truck. Their moonshine operation was closely tied to violence, with Jack’s son recalling small but vivid details like rusty brass knuckles hanging discreetly around the house and the unmistakable sound of glass bottles clinking during their drives. Jack passed away before his son and grandson could ask him more about his bootlegging days, leaving most of what is known about them in fragmented memories. They know about the notorious shootout at Maggodee Creek, where a corrupt cop ran a protection racket for the bootleggers in the area. Jack once casually mentioned an old gunshot wound he had received in the shootout, but little else was revealed about his past.
Family stories also suggest that Forrest, the middle Bondurant brother, was seen as something of a lucky charm. One such tale tells of him surviving a throat slashing, walking through the snowy Appalachian Mountains in search of help. Matt Bondurant, his grandson, believes his grandfather's refusal to speak about his past wasn't out of shame for his criminal activities, but rather out of a practical reason: talking about it could get both you and your partners killed.
3. Dutch Schultz and His Buried Treasure
Arthur Flegenheimer, after a tough upbringing, decided his name no longer fit the man he was becoming, so he adopted the tougher name of Dutch Schultz, or 'The Dutchman.' By the time he was in his early twenties, he had already joined a gang in the Bronx smuggling liquor into the city (a gang member leaving court is pictured above), often stealing from other bootleggers and selling their stolen goods. By the late 1920s, he cut ties with the gang and struck out on his own. Soon after, he controlled the distribution of all beer in the Bronx.
His earnings soared, aided by the slot machines he installed in the establishments where patrons consumed his alcohol. Much of his life mirrors the chaotic tales of upset gangsters and botched hits, with the glaring exception of the so-called Baby Massacre—an assassination attempt that backfired, resulting in four children being shot, one fatally. After this incident, law enforcement shifted its focus to Schultz, and like many of the bootleggers and gangsters of the Prohibition era, they eventually caught up with him.
However, Schultz was determined not to let his fortune slip away to law enforcement, the government, or even his fellow gangsters. According to the legend, Dutch Schultz hid his wealth, which included both cash and valuable gems, in a tin trunk. He carried this trunk with him when he made his escape from New York City, heading into the Catskills. The story tells of Schultz jumping off a train near Phoenicia, where he buried the trunk to safeguard his treasure.
He was gunned down shortly after in a 1935 shooting, and the legend of the trunk has since become part of the foggy folklore. Some locals are convinced that the treasure, which is estimated to be worth around $83 million in today's currency, remains hidden along a riverbank. Others dismiss the tale as pure fiction. Nevertheless, this hasn’t stopped treasure hunters, though nothing has been found—yet.
2. Daisy Simpson
Without law enforcement agents like the determined Daisy Simpson, bootleggers would have had no reason to take any precautions. Simpson, one of the few female Prohibition agents, worked the streets of San Francisco—streets she had once walked as a lawbreaker herself. A former drug addict, Simpson turned her life around and joined the Prohibition squad, dedicating herself fully to the role. Known for her extensive wardrobe of 100 different disguises, she led raids on speakeasies, bars, restaurants, and private gatherings. To gather evidence, she would often slip into one of her costumes and blend in at the establishments she targeted, arresting those who served her alcohol.
However, Simpson occasionally went too far in her pursuit of justice, earning reprimands from judges for her overzealous actions. She was responsible for the seizure of 8,000 gallons of wine from a single winery, but she also testified in court against a bellboy who had brought her medicinal whiskey after she complained of stomach pains, and a man who had a single jug in his car that smelled suspiciously like moonshine.
Eventually, illness took its toll on her, and Simpson relapsed into her former drug addiction, leading to her arrest in Texas. Devastated by her failed marriage and the collapse of her career, she smuggled a gun into jail and shot herself in the stomach. After a long and painful recovery, she posted her bail, returned to California, and faded into obscurity.
1. Maggie Bailey
Maggie Bailey began crafting and selling her own moonshine during Prohibition, and her passion for it didn’t wane even after the law changed. In fact, she continued her moonshine operation for nearly 90 years. Throughout that time, she was constantly pursued by law enforcement, both during and after Prohibition, as the white moonshine she produced was illegal, even after the law was repealed. Despite their efforts, state and federal agents struggled to secure a conviction against the Kentucky woman, who would often show up to court wearing a flower-patterned apron, her gray hair and grandmotherly presence softening her defiant image.
The reason for her string of acquittals was likely her deep connection to the community. Bailey wasn’t just known for supplying liquor—she had a genuine relationship with the people she served. During the Great Depression, when many were struggling, she would offer gallons of liquor on credit, allowing others to sell it, pay her back, and earn a little extra income for themselves. Bailey was familiar with everyone in town and always kept an eye out for those in need, frequently delivering food to hungry families and even helping fund children’s educations. She also took care not to sell to children or anyone she knew had issues with alcoholism.
Over the course of nearly nine decades of bootlegging, Bailey served a mere 18 months in jail for the only conviction that ever stuck. She passed away in 2005 at the age of 101, often saying that the thrill of her moonshining days was what kept her feeling young.
