This episode of "Calm History" delves into the law breakers of Prohibition, focusing on rum runners and speakeasies. It begins with the history of rum, tracing its origins to sugarcane, domesticated around 8,000 BC in New Guinea. Sugarcane juice was boiled to produce sugar crystals, leaving molasses—a waste product that was later fermented and distilled into rum, first documented in the Caribbean in the 1650s. Rum became popular in the American colonies, leading to smuggling to avoid British taxes. During Prohibition (1920-1933), illegal alcohol smuggling surged, with "rum running" referring to maritime smuggling and "bootlegging" to land-based operations. Legendary rum runner Bill McCoy became known for selling unadulterated, high-quality booze, possibly inspiring the phrase "the real McCoy." Smugglers used large ships anchored offshore and fast boats with hidden compartments, smoke screens, and even machine guns to evade the Coast Guard. Speakeasies, secret bars where patrons spoke quietly, exploded in number, with New York City hosting around 32,000 by 1930. These venues often promoted social mixing across racial and gender lines, and owners used clever concealment methods, like secret cellars behind brick walls, to avoid police raids. The episode highlights the ingenuity and risks of this illegal trade, emphasizing its profitability and cultural impact.
Welcome to calm history. I'm Harris, and this podcast is my quirky mix of education with sedation. So go ahead, lean back, put up your feet, and settle into my time machine of tranquility. I hope this episode distracts and relaxes your overactive brain squirrels. In my prior episode about prohibition, you learned about the law enforcers who chased those who broke the laws during prohibition. In this episode, you'll learn about the law breakers who ran from the law enforcers during prohibition, including lots of fascinating facts and stories about rum runners and speakeasies. You'll also learn about the history of rum, the origin of the popular expression, the Real McCoy, and the origin of the restaurant expression to 86 something. In the near future, I'll stitch together this episode and my prior episode of prohibition so you can relax with a one hour, silk plus bonus episode about the wild era known as prohibition. But for now, the history of rum, rum running, and speakeasies. Before I get into the dirty deeds of rum runners, let me begin with the history of rum and where rum comes from. Do you know the type of plant needed to create rum? A rum raisin bush. That's your guess. You think rum comes from a rum raisin bush? Usually, you have great guesses, but that's a terrible guess for so many reasons. And no, rum is also not created from rum balls, rum cake, rummage sales, rumbles still skin, rum roast, or any other common words that begin with the letters, R-U-M. On the other hand, rum is produced by an item that ends in the letters, R-U-M. That item is a specific type of grass that begins with the Latin name, saccharum. Yeah, it's a word that means sweet and it ends in the letters that spell rum. How perfect. This plant, with the technical name of saccharum, is better known as sugarcane. Can you guess the name of the person who gave sugarcane its scientific Latin name? Yeah, it was Carl Leneas, that cranky scientist from bonus episode number 39 who loves hanging out with reindeer in Lapland. Time for a quick break. You can access over 120 more episodes of calm history, all without any ads or breaks by becoming a silk plus member, and it's free for limited time. If interested, tap the link in the episode notes or go to calmhistory.com. Alright, back to the episode. Sugarcane was first domesticated for human use on Papa Nukeini about 10,000 years ago. I'm sure you can guess why. I grabbed one of these 15-foot tall plants, chewed on it and said, "Dang, that's pretty sweet and tasty." So since at least 8,000 BC, people have enjoyed chewing on these tall sweet plants. At some point though, someone bashed some sugarcane stalks between two rocks and discovered an even sweeter liquid. This sweet liquid was sugarcane juice, similar in concept to squeezing grapes and getting grape juice. At this point, sugarcane and sugarcane juice began spreading around the world. Around 500 BC, perhaps in India, someone decided to boil the sugarcane juice to see what might happen. When this solution cooled, they found that crystals of pure sugar had formed. These crystals of sugar are also called granulated sugar. Yeah, that's the same stuff you buy in a grocery store today. So since 500 BC, people have been boiling sugarcane juice so they can create, eat and sell granulated sugar. After you remove the sugar crystals from the boiled sugarcane juice, what remains is a thick black, sweet, goop. Yip. That there is molasses. The role most of history, molasses was considered a waste product from making crystalized sugar. Molasses was the sweetener of poor people, and it was often fed to slaves, servants and cattle. On the other hand, crystal sugar was the high value sweetener that was consumed by the rich. Over time, the cost of crystal sugar came way down, making it affordable to all classes. Well, except cattle, they still couldn't afford it because they don't have money, or hands to hold money, or pockets to put money in. Okay, you get the point. While crystal sugar came down in price and was enjoyed by everyone, except cattle, molasses became even less favored. In fact, places that produced crystal sugar often discarded most of it due to high supply and very low demand. Until someone discovered that you could turn molasses into something very special. Yip. Molasses could be turned into rum. Now the general method for turning plants and fruits into alcohol had been known for thousands of years. It takes some juice from some edible plant, add some yeast, allow it to ferment, and then enjoy the alcohol. Even as early as 6,000 BC, people were adding yeast to grape juice and fermenting it into wine. So it eventually dawned on people, why not do the same with sugar cane juice or molasses? Finally, people started making rum, at least 700 years ago. They added yeast to molasses or sugar cane juice, allow it to ferment, and then separate it out the alcohol by using heat and distillation. This process of creating rum or something similar has occurred in various places around the world. In the 1300s, Marco Polo described an alcoholic drink made from sugar that he tasted in modern day around. As early as 1520, there are reports of the production of rum in Brazil. In the late 1500s, a fermented beverage made from molasses was described in Puerto Rico. In 1628, a Swedish warship named Vasa Sank, much later,
where a tin bottle of rum was discovered in the shipwreck. But when you think of rum today, you probably don't think of, around Brazil, Puerto Rico, or Sweden. Instead, you probably think of some Caribbean islands, like Jamaica or Barbados. In the mid-1600s, sugar plantations started popping up on several Caribbean islands, especially Barbados. In 1651, a document was written that describes a drink on Barbados, which was likely rum. Now, I gotta give you a little warning. There are a couple of spicy words in this reference, so cover any sensitive ears that are nearby. Here is what the document stated. The main alcoholic drink they make in the island is rambulian, also known as Kieldevil. This drink is made of distilled sugar cane and it's hot, hellish, and terrible liquor. Let me highlight several important parts of this statement. First, rum may have been called rambulian initially, and then later shortened to rum. And rum was also called Kieldevil, yikes. Third, rum in the 1600s seemed to taste like the backside of a sweaty donkey. Most historians agree that the earliest versions of rum probably tasted quite different than any rum you would taste today. Unless you make your own rum in your basement from molasses and donkeys wet. Within just a few years, the Caribbean distilleries improved their recipes and rum started becoming more popular than brandy. In 1655, the British Navy even changed the daily ration of liquor given to sailors from brandy to rum. Rum was also becoming popular in the British colonies of North America. In 1664, the first rum distillery was established in New York, and three years later, another one popped up in Boston, Massachusetts. Rum soon became New England's largest and most prosperous industry. To create all of this rum, New England colonists were using a lot of molasses, and it wasn't all purchased from British controlled sugar plantations. So in 1733, Britain put a tax on all imported molasses that wasn't from a British sugar plantation. The American colonists didn't like this one bit, so guess what they did? No, they didn't start the American revolution. That would take a few more decades. They did something more immediate and direct. That's right, they started smuggling molasses into the colonies to avoid the taxes. And then they realized the next obvious step. If you're going to smuggle in molasses just to make cheaper rum, why not just smuggle in cheap rum? And so began the history of smuggling rum into the American colonies. It even continued after the colonies became independent from Britain. Making smuggle items and reselling them is an irresistible business model due to low overhead and high profits. During the 1700s and 1800s, pirates from the Caribbean were part of this smuggling circus. They would steal rum off Caribbean ships, sail up to the colonies, and sell the stolen rum directly to the colonists. In the 1800s, some colonists would sell illegal rum and other alcohols from flasks that they hid in their boots. This led to the term "bootleger". What about the term "rum running" or "rum runner"? These terms didn't come into existence until the early 1900s. Right about the time of prohibition in the US. This dry era began in 1920 and lasted until 1933. During prohibition it was illegal to produce, import, transport, buy and sell alcohol. As a result, this gave a huge boost to the smuggling of rum often referred to as "rum running". The term began when ships from the Bahamas smuggle cheap Caribbean rum into Florida. So what's the difference between rum running and bootlegging? Technically, bootlegging is smuggling booze across land and rum running is smuggling booze across water. But both terms tend to be used interchangeably. This episode is brought to you by Warpy Parker. Let me share something. My past experiences with buying eyeglasses have been complicated, overpriced, and full of styles that were probably last worn by the dinosaurs. Until I recently tried Warpy Parker, I was quite impressed with their prices, selection, and use of modern technology. For example, I could try on any eyeglasses or prescription sunglasses, virtually, by using the camera on my phone. Oh yeah, you bet I picked out some new shades. Check out was super easy. My glasses arrived quickly, looked fantastic, and fit perfectly. Right now you can buy one prescription pair and get 20% off additional pairs by going to WarpyParker.com/SILK. I also put that link in the episode notes and using it helps to support the show. Thank you. Now if you'd prefer to hear episodes without any ads, well, I also put a link in the episode notes for that option. Now rum running was so profitable that ships started smuggling rum to the major cities of Boston, Chicago, and New York City. Of course, not everyone drank rum. So these ships also smuggled in whiskey, gin, and champagne. This expanded the meaning of rum running to include the smuggling of any type of alcohol. So almost any time that you hear the term "rum running" in real life or in the rest of this episode, it's probably referring to the smuggling of all alcohol types. As you can imagine, being a rum runner was highly profitable due to the high demand during prohibition, but there was another way to boost your revenue. Rum runners often added water to the bottles of booze. Watered down alcohol or any type of low-quality booze was often called "hooch" or "rot-cut". Runners also had another
trick. Some of them replaced the labels on bottles of cheap booze, with labels from high quality booze. So if you were buying smuggle booze, you never knew what you were really getting. Unless you bought your smuggle booze from Bill McCoy, a legendary rum runner. McCoy was well known for never adding water to his bottles. And you could always trust his labels. Therefore everyone knew that if you purchased illegal booze from Bill McCoy, you always got the real thing. In fact, he is credited as the origin of a popular expression that means the real thing. Yeah, many believe that Bill McCoy was the origin of the expression. Say it with me, the real McCoy. Except there's a problem with this theory. The phrase the real McCoy to refer to a a genuine thing. Appeared in print in 1881. Let me run the math on this. B.B. B.B. B.B. B.B. B.B. B.B. B.B. Bill McCoy was four years old in 1881 and I'm pretty confident he wasn't a rum runner at that point. The expression may have originated before Bill McCoy was even born. The real McCoy may have referred to a reliable oil drip collection device invented by Elijah McCoy in 1872. Regardless, it's still true that Bill McCoy, the grown man, was known for selling high quality booze during prohibition. Now McCoy wasn't just a rum runner legend for his quality booze. He also pioneered many of the methods used during prohibition. At the start of prohibition, the boats that smuggled in booze were small, battered fishing boats. These slow clunky boats worked well because the coast guard hadn't yet caught on to a much booze, was being smuggled into the US. But after a few months, the coast guard did realize the problem and started chasing and easily catching these clunky vessels as they came to shore. This is when Bill McCoy devised a new system which was so effective many other rum runners copied it. He used large vessels like a schooner to bring the booze to the edge of US waters about three miles offshore. This kept him out of the reach of the US Coast Guard. McCoy then sold the booze to smugglers who were in smaller, faster vessels. These smaller vessels had strong motors, low profile hulls, hidden compartments, and wireless communications. They also kept cans of used engine oil on board. If a chase ensued, they would pour the oil on their exhaust manifolds to create a smoke screen. Yeah, like a James Bond movie or something. Some of these rum runners even used speed boats with aircraft engines, machine guns, and armor plating. So yeah, most of these faster boats could easily outrun the coast guard ships. But that was always Plan B. Plan A was to not even get detected by the coast guard. To achieve this, these small boats often ran at night and in the fog without any lights. Sure enough, some of these vessels would crash or sink after hitting a sand bar or reef at high speed. As a result, shores nearby were sometimes littered with free bottles of smuggled booze. The rum runners' loss became the beachcomers' gain. The rewards often outweigh the risks for most rum runners. In fact, the captain of a rum running vessels could make more than $100,000 a year. Compare this to the annual salary of a coast guard commander, which was only $6,000 a year. This meant that bribery was a frequent problem. You know who often braked that he never braved the coast guard? Yep. Bill McCoy but perhaps he should have. By 1923, Bill McCoy was a primary target of the US coast guard. They had even gotten permission to capture him if he was outside US waters. On November 23, 1923, a coast guard vessel caught up to McCoy's schooner and pulled up next to it. 15 coast guard officials then boarded McCoy ship. Not ready to give up, McCoy hoisted his sails and began to move away from the coast guard vessel. This was a bold move. He had 15 coast guard officials on his ship and the large gun of the coast guard ship was pointed at him. So if you think this sounds like a terrible idea, I agree. Sure enough, the coast guard ship fired its gun across the bow of McCoy ship. Was McCoy defenseless in this situation? No. He had mounted a large machine gun on the bow of his ship years ago, continuing to be bold and perhaps stupid. McCoy fired his machine gun back at the coast guard ship. The large gun of the coast guard ship returned some final warning shots, putting large caliber shots into the water next to McCoy ship. This may sound like a fair fight, but I ran the map on the bullet sizes. The coast guard were firing shots that were about 15 times larger in diameter than the shots being fired by McCoy. Yeah, we're talking about large shells, small bullets. Those shells from the coast guard were so large that when they hit the water, they splashed water onto the deck of McCoy ship. Some McCoy finally did something smart. He surrendered. Not long after that, he pleaded guilty in court and then spent nine months in a New Jersey jail. Today, you can find Bill McCoy appearing in nine episodes of the HBO TV series, Boardwalk Empire. Of course, you'll be watching an actor playing him. That's not the real McCoy. I'm pausing so you can groan at my stupid pun. Are you done rolling your eyes? Okay. Let's now move on to Speakecies, also known as Juice Joints. These were the places where a lot of the smuggled booze ended up. They were semi-secret places that sold illegal alcohol. They were called Speakecies because you were supposed to speak quietly, so no one realized that a major rager was happening inside. Similar to smuggling, Speakecies existed before prohibition. Many of these early Speakecies
either sold illegal alcohol or sold legal alcohol without a license. Around 1890, it's estimated that Pittsburgh, Pennsylvania had about 92 legally licensed liquor dealers. But it had about 700 speakers. Overall though, this wasn't a national problem. It was a Pittsburgh problem. Two years earlier, this city had jacked up the cost of a liquor license, from $50 to $500. Yeah, what they think was going to happen. The smog from the steel factories must have been clouding their brains. A national explosion of Species in the US didn't occur until the start of prohibition in 1920. If you thought Pittsburgh's 700 Species in 1890 was a shocking number, then hold onto your eyelashes. Guess how many Species were in New York City near the end of prohibition? Well, before I tell you the answer, let me put it in context. Today, in 2025, there are somewhere between 2000 and 10,000 bars in New York City. So, how many Species do you think were in New York City in 1930? The answer is, about 32,000. Yeah, you're blinking your eyes so fast right now that your eyelashes just flew off. On a more sobering note, no pun intended. There was a curious upside to speak easy. Prior to prohibition, most bars and saloons were segregated. It was rare to see people of different races or ethnicities drinking together. But during prohibition, people were so happy to find some place to booze it up that many put aside their prejudices and mingled with the diversity of other patrons. Some women even discovered more independence in freedom at Species, including being profitable owners of these forbidden locations. One female owner of a Species e, created each customer with "hello, sucker." I'm pretty confident that they don't teach that type of greeting at the Wharton School of Business. But to be frank, I'd love to be greeted with such honesty and snark. Imagine walking into Macy's today and being greeted with "hello, sucker. How much money can we take from you today?" Well, thank you for being so straightforward. I feel it's better than being greeted with "hello, sir. How can I help you today?" If I replied with "Well, you can help me by cleaning the bird poop off my car." They'd frown at me. But why? They offered to help me. "Oh, because when they said, 'How can I help you today?' What they really meant was, 'How can you help us make more money today?' All right, enough of that. Back to the regular program." Now, similar to smuggling, there were huge profits to be made for almost any owner of a Species e. Sure, police often discovered them and gave them fines. But the money was so good that they would just keep doing it. For example, the Dill Pickle Club in Chicago during prohibition received 150 citations. Unlike the Dill Pickle Dumb Dumb Club, other clubs tried a lot harder to avoid detection and those pesky citations. The 21 Club, a Species e. in New York City, understood rule number 1 of not getting caught. Don't stay in the same place. The club relocated several times, and each time they changed their name. But relocating a club gets annoying and expensive, so they came up with a better plan. They realized that they didn't need to hide the whole club. They only needed to hide the booths. After their last relocation, they renovated the inside very carefully. They started by building a secret cellar to store all the illegal booths that wasn't being served. To access this secret cellar, you passed through a hidden door in a brick wall and walked down into a basement that was under the building next door. Okay, that's great. But what did they do when police raided the club and saw all the illegal booths that was being served? As soon as a raid began, any open bottles were quickly placed on shelves above the bar, next to any bottles that hadn't been opened yet. A system of levers was then used to tip the shelves upwards. All the bottles in the shelves would fall backwards into a hidden chute. The hidden chute then carried all the illegal booths into the city sewer system. Brilliant. But how did Speakeasy's know whenever he was on the way? I don't know how every club did it, but I do know how the built-more hotel in Phoenix, Arizona did it. The hotel used a special room. They called the mystery room as they were Speakeasy. Of course, the sign outside the room didn't say "mystery room" or "speakeasy hidden here." Instead, the deceptive sign to the room simply said "men smoking room." Okay, this isn't exactly the depth of trickery. You might see an emission impossible movie. But hold on, there are many layers to this room. The next layer included a secret password for entry into the room. You know, like the blue monkey has a banana for an arm. The next layer was their alert system. The Speakeasy room was on the top floor of the hotel and the room had a skylight. This is key. A hotel employee stood on the roof of the hotel next to the skylight and that person watched out for cops on the streets below. When the employee on the roof spotted cops rushing into the building. They flashed a bright spotlight through the skylight and down into the Speakeasy room. Inside the room, hotel staff would hide the entire bar behind a hidden revolving bookcase. When cops would peek into the room, all they would see is the bookcase. But what about all the guests that were in the room? The drunk guests didn't exit out the main door of the room because they might bump into the cops in the hallways. Instead, they used another exit door that was sealed off and hidden from the main hallway. This door led to secret passageways that took the guests directly to their hotel rooms. Brilliant times two. Another Speakeasy in New York City called "Jumlies" also used methods of secrecy. They kept the alley.
outside of their joint, unmarked and nondescript. There are not any signs at all. You know, it's that simple and classic method of. There's nothing to see here. Move along, move along. But that's not all they did, of course. Inside the building, they had hidden doors, some trap doors, and secret stairs. Did they also rely on a system of spotlights to be alerted about raids? Nah, their system was the same method that you would probably use today, the handy phone call. It seems they had some insider connections who would call them if a police raid was on the way. When the speak easy received the call, the guests would be escorted out the backside of the building. Now, here comes a fun fact. The backside of the building had the address of 86 Bedford Street, which was different than the address to the front side of the building. So when a raid was on the way, the person on the phone gave this secret message, 86 the customers, which meant to escort them out the rear exit door that opened on to 86 Bedford Street. The chumly speak easy, also used this same expression anytime, a customer got unruly and was tossed out the back exit. They would say that the customer was 86. Many people believe that this speak easy was the origin of 86 as an expression for something that is removed, deleted, or out of stock. If you've never heard of the expression to 86 something, then it's likely that you've never worked in the food industry before. When a restaurant runs out of your favorite rum raisin ice cream, the people in the kitchen shout, 86 rum raisin. This alerts all the servers to remove it from the menu, which I'm sure makes you scoff and say, "Well, if they grew their own rum raisin bushes behind the restaurant, then they wouldn't have run out." Yeah, so negligent. This is the end of the episode. To enjoy over 120 more episodes of calm history, all without any ads or any breaks, then just become a silk plus member. It's free for limited time. If interested, tap the link in the episode notes or go to calmhistory.com.
Podcast Summary
Key Points:
The episode explores the history of rum, rum running, and speakeasies during Prohibition, contrasting with a prior episode on law enforcers.
Rum originated from molasses, a byproduct of sugar production from sugarcane, with early production in the Caribbean and consumption in the American colonies.
Prohibition (1920-1933) boosted illegal alcohol smuggling, known as rum running (by sea) and bootlegging (by land), with figures like Bill McCoy pioneering methods and inspiring the phrase "the real McCoy."
Speakeasies, secret bars selling illegal alcohol, proliferated during Prohibition, with New York City having about 32,000 in 1930, fostering social mixing across races and genders.
Smugglers and speakeasy owners used tactics like hidden compartments, smoke screens, and secret cellars to evade law enforcement, often bribing officials due to high profits.
Summary:
This episode of "Calm History" delves into the law breakers of Prohibition, focusing on rum runners and speakeasies. It begins with the history of rum, tracing its origins to sugarcane, domesticated around 8,000 BC in New Guinea. Sugarcane juice was boiled to produce sugar crystals, leaving molasses—a waste product that was later fermented and distilled into rum, first documented in the Caribbean in the 1650s.
Rum became popular in the American colonies, leading to smuggling to avoid British taxes. During Prohibition (1920-1933), illegal alcohol smuggling surged, with "rum running" referring to maritime smuggling and "bootlegging" to land-based operations. " Smugglers used large ships anchored offshore and fast boats with hidden compartments, smoke screens, and even machine guns to evade the Coast Guard.
Speakeasies, secret bars where patrons spoke quietly, exploded in number, with New York City hosting around 32,000 by 1930. These venues often promoted social mixing across racial and gender lines, and owners used clever concealment methods, like secret cellars behind brick walls, to avoid police raids. The episode highlights the ingenuity and risks of this illegal trade, emphasizing its profitability and cultural impact.
FAQs
This episode covers the history of rum, rum running, and speakeasies during the Prohibition era in the United States.
Rum is made from sugarcane, specifically from molasses or sugarcane juice that is fermented and distilled.
The phrase may have originated from Elijah McCoy's oil drip invention in 1872, though rum runner Bill McCoy is also credited for selling high-quality booze without watering it down.
Rum running refers to smuggling alcohol across water, while bootlegging involves smuggling it across land, though the terms are often used interchangeably.
They used large vessels to stay outside US waters and sold to fast, small boats that used smoke screens, night operations, and hidden compartments to evade capture.
A speakeasy was a secret bar that sold illegal alcohol during Prohibition, named because patrons had to speak quietly to avoid detection.
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