Holiday Edition: A Speakeasy Christmas
Like every good Holiday story, it was Christmas eve and the snow was falling. It was covering all of Chicago and made everything look pure, fresh and innocent.
Aunt Margaret was having her annual Christmas party and as last year and the year before, it was a little lame. As you might imagine, there was the same cheese and crackers and fruitcake. Beyond that there was the gossip on everything in the neighborhood and church. That's when your favorite cousin Joey slipped you a folded note during dinner. Like the sneak he is, he carefully tucked it underneath your hot chocolate and saucer. Something tonight was going to be different.
On the note was a single word. Poinsettia,". Below that was an address you didn’t recognize, but it wasn’t in the area.
While the house hummed with conversation and gossip, you walked to the door and threw on your coat and wrapped your neck in a festive red and white stripped scarf. It went perfectly with your green sweater. You figured this was the right touch of holiday spirit. As you snuck out the door, the neighborhood was quiet. Most of the families were having dinner and putting the little ones to bed. Everyone was preparing for Christmas morning. But not you. You had other plans.
You walked down the street and came to a door that looked like all the others and was covered in snow But this was the address. When you knocked on the door as your cousin Joey instructed you, a small window slid open. As you looked out the window, you saw an older man wearing a Santa bowler hat staring at you. You whispered "Poinsettia,"
The door opened and inside was a world unlike one you’d seen before. This wasn’t the typical underground bar. This was something special. It was a magical Christmas wonderland that had an electric vibe to it. Green garland wound around the mahogany bar, and festive glass ornaments and strings of lights cast a warm glow.
Looking around the place you saw a small Christmas tree in the corner, decorated with tiny liquor bottles, mini corkscrews and shot glasses. Tinsel throw on the branches sparkled as the colorful lights reflected off them. It was a festive setting that took you back to your childhood.
In the corner, the band played a jazzy version of "Silent Night" that was upbeat but not overpowering. One of the band members playing the trumpet wore a Santa hat tilted to the side with a big bright Santa’s jacket
As you walked up to the bar, it was alive with Christmas spirits. Spirits of a different kind. The most popular drinks that night were served in glasses rimmed with crushed candy cane and mixed with nutmeg and cinnamon. You carefully considered for a moment on your first drink. A "Christmas Conspiracy" the bartender said. It was made with whiskey and a touch of peppermint, that was festive and strong enough to warm you from the inside out.
Everyone was dressed in their holiday best. Men in suits with subtle Christmas touches of green and red. Women wore beaded dresses that sparkled and were festive, but not too festive. This night was special, but it was still a place of secrets.
You couldn't help but think to yourself and laugh. You remember when you left your aunts. Everyone was preparing for Christmas morning. Putting the kids to be and leaving milk and cookies for Santa. But not you. You were here in a hidden bar in a hidden world. You thought, this is where the real spirit of the season was being celebrated. Everyone here was having fun with no judgment.
As you looked around the room you saw a small group of men playing cards, Christmas music was playing softly in the background and glasses filled with your favorite holiday spirit were clinking. People were toasting "Merry Christmas," and they laughed about being on the naughty list.
This is what it was like to celebrate Christmas, prohibition-style. This was a celebration of friendship, and taking in the special moments most of the world didn’t see. It was you and your speakeasy family enjoying secret holiday spirits that truly make the season bright.
Here's an imaginary story that captures the dangerous and exciting life of a bootlegger.
Note: A bootlegger was an illegal alcohol distributor during the Prohibition period in the United States (1920-1933), when the manufacture, sale, and transportation of alcoholic beverages were banned by the 18th Amendment. The term "bootlegger" originally came from the practice of hiding liquor bottles in the tops of boots, but it evolved to describe anyone involved in smuggling and distributing illegal alcohol.
And so the story goes... Tommy Malone waited nervously in his Ford Model A, while the engine purred in the night. In the trunk were cases of Canadian whiskey, hidden beneath a layer of potato sacks.
It was 1927 and prime time for prohibition where the liquor trade was both dangerous and lucrative. Tommy was running booze for a group of speakeasies across Los Angeles. Working underground bars was his life. He was paying top dollar for each case of smuggled alcohol. It was lucrative and a single run could net him $5,000, which was considered a fortune during the Great Depression.
Tommy planned the route carefully. He knew the back roads and where potential police checkpoints were. He also had a team of lookouts as well as corrupt cops. Tommy modified his car with reinforced suspension to handle heavy loads and it was also equipped with hidden compartments to stash extra liquor.
Approaching the city limits, Tommy signaled with a pattern of headlight flashes to give his contacts a heads up. Speakeasy owners would be ready and waiting to stock their hidden bars. The money they paid was worth it as patrons paid top dollar for a single drink.
The risks were certainly huge and if caught, Tommy could face serious jail time. Especially considering federal agents, local police, and rival bootleggers all posed constant threats. Not only would Tommy’s car be confiscated, but his network exposed. Even worse, he could be killed, either by law enforcement or competing smuggling gangs looking to control territory.
It was a tough trade off. Because the money was great and it was too good to resist. Tommy worked with a local distillery that produced moonshine, supplementing it with imported Canadian and European liquor smuggled across the border. There was a steady stream of demand from local speakeasy owners, including a few run by gangsters,
Payment was always in cash, and the transaction was often in a pre-arranged location. No receipts, no paper trail. A handshake and a stack of bills was how they handled their business. Speakeasy owners marked up the liquor by 500% or more and it made everyone in the supply chain wealthy.
As Tommy approached the back entrance of O'Malley's speakeasy, he knew another one of his bootlegger runs was almost over. As before, he whispered the password, the hidden door opened and the deal was done.
Someone said the most transformative moments in music history rise from resistance and restriction.
Imagine standing in an old speakeasy somewhere on Chicago's South Side. Picture trumpet solos and piano riffs that filled this place during the Prohibition era. The year 1920 wasn't just the beginning of a ban on alcohol, it sparked a cultural revolution that changed the landscape of American music forever.
Speakeasies were more than just hidden bars. What came about from this time was artistry and creativity. It was a breeding ground for jazz innovation. Prohibition forced alcohol consumption underground, and when it did, it created a sanctuary for musicians. Many who had previously struggled to find work.
Doing research on speakeasies and the impact on what was created during this time amazes me. Black musicians, who were often barred from performing in numerous venues, found opportunities in these hidden bars where racial boundaries blurred.
Let’s take the well known Cotton Club in Harlem. It had a whites only admission policy, but it became a launching pad for Black artists like Duke Ellington, Cab Calloway and many more. This is where Ellington's orchestra refined their signature sound. By playing nightly to packed houses of rich white patrons. Most who have never heard anything like it before.
The secrecy and allure of speakeasies helped shape the evolution of jazz. These intimate, crowded rooms needed a different type of music. Bands and musicians had to adjust on the fly by, controlling their volume and mutes, and developing more intricate arrangements in close quarters. This is where "chamber jazz" originated and it helped develop harmonies that would eventually define this genre.
What is fascinating about the prohibition era is how speakeasies played a major role in influencing musical innovation. This atmosphere and the need for musicians to be discrete led to new instrumental techniques. It’s where horn players had to learn how to play more softly, but with greater expression. It’s where drummers invented brush techniques to keep the rhythm softer yet alive in the small venues. You could say every limitation bred a special type of creativity during this era.
There was also the social aspect of speakeasies that was equally revolutionary. Musicians from this era described how these venues created extraordinary mixing between races, classes, and genders. You would have wealthy whites sit next to working class patrons, all gathered together to hear mostly Black musicians perform. This was unprecedented and created cross cultural exposure that helped jazz spread from its origins in the Black community to one of America's most distinctive sounds.
The evolution in musical trends came about in 1921-1922, with the emergence of what became known as "Hot jazz”. This included more improvisation and emotional expression. By 1923-1924, the "Chicago style" was taking shape and it included mixing in New Orleans style traditions with faster tempos and more complex arrangements. These trends spread from city to city through musicians who played the speakeasy circuit.
Some of the most enduring jazz standards were born in these hidden bars. If you listen to recordings from that era, you can hear how the intimate atmosphere influenced the composition style, songs needed to work both as dance numbers and as sophisticated listening pieces for the seated audiences sipping their illegal drinks.
The speakeasy's influence extended beyond music and into club design. There was a new kind of performance space that would influence club design for decades. Speakeasies were intimate and that meant a small stage and a very close proximity between musicians and the audience. This emphasis on atmosphere and intimacy became fundamental to how we experience jazz music today.
What’s ironic is that Prohibition intended to impose some kind of moral order, yet it actually created spaces where artistic independence thrived. Speakeasies became more than just a place to drink. It was a trial for cultural change. This is where jazz evolved from regional folk music into a sophisticated expression of art that would influence musicians globally.
The speakeasy legacy lives on in intimate jazz clubs where musicians and audiences share that closeness that can only happen in small, personal spaces. It's a reminder that powerful cultural movements emerge not from freedom, but from restriction. Like a flower growing through cracks in the concrete.
The Prohibition era, which ran from the 1920s to early 1930s, was a dangerous time for law enforcement. Traditional urban areas became battlegrounds between the authorities and those who were determined to sell and drink alcohol. Authorities, which included federal agents, local police, and prohibition officers were in a constant cat and mouse game with bootleggers, speakeasy owners and patrons.
For law enforcement, identifying speakeasies wasn’t easy. They tried multiple strategies to try and uncover these underground bars and establishments.
Some of these strategies included the user of informants. Police had an extensive networks of informants, ranging from disgruntled employees to rival business owners, and community members willing to provide tips on hidden bars. These informants were typically motivated by cash rewards or holding a personal grudge.
Another strategy employed wete undercover operations. Agents would disguise themselves as travelers, businessmen or part of the working class to try and infiltrate suspected speakeasies. They would stake out and observe operations and gather any intelligence on the speakeasy’s owners and patrons.
A third strategy was surveillance. Here, law enforcement teams would monitor establishments to track foot traffic and observe delivery patterns. Watching for signs of alcohol distribution was another sign. Nighttime surveillance was key as the authorities could pay attention to locations with signs of nightlife or unusual visitor activity.
Another strategy that didn’t involve stakeouts was viewing financials.
Treasury agents tracked financial transactions looking for suspicious accounting or unexplained sums of money. bank records were key tools used to uncover hidden speakeasy operations.
When law enforcement successfully identified a speakeasy, the raids were fast and dramatic.
The first step authorities went through was to obtain search warrants, although some raids used less formal legal procedures. Especially during the height of Prohibition.
Raids were usually at night or during operating hours. This gave authorities a greater chance of catching owners and patrons in the act. They also blocked potential escape routes before raiding the bar.
Next Officers would secure the premises and confiscated any alcohol, bar equipment, and other goods tied to alcohol production or distribution. They quickly arrested owners, bartenders and sometimes patrons to prevent them from destroying evidence. Penalties varied, but typically included fines, jail time, and losing their liquor license.
One dramatic component of the raids was to immediately confiscate and destroy all alcohol and brewing equipment.
Law enforcement did this publically to demonstrate their commitment to Prohibition. Agents would empty all barrels, bottles, and kegs of illegal liquor in public. In addition, brewing equipment, storage containers, and bar tools would be seized and potentially used as evidence.
Despite the authorities aggressive tactics, it was still a cat and mouse game going up against criminal networks and corruption within police departments.
The illegal alcohol trade was very profitability and many speakeasy owners would bribe and pay off police officers and local officials. This corruption was sophisticated and often undermined law enforcement’s efforts.
The war against speakeasies was very complex. While law enforcement used various strategies during the prohibition era, there were many challenges. In addition to widespread public resistance, there was opportunity with money and power being driving forces. The authorities continued to raid these hidden bars, but speakeasies continued to thrive, and ultimately contributed to the repeal of Prohibition in 1933.
I hope you enjoy my attempt at a punny tale of speakeasy shenanigans.
It was a dark and stormy night, not that it mattered, since the bar I was about to enter had no windows. I stood outside a nondescript laundromat called 'Pressing Matters,' clutching a piece of paper with a single word scrawled on it… Negroni. A shadowy figure stepped out of the darkness.
“Password?” he rasped.
I held up the paper.
“Ah, Gin-ius!. How gin-erous of you to join us,” he said with a sly grin, sliding open a hidden door that blended seamlessly into the wall. “Welcome to The Last Straw.” The only place where our spirits are higher than the temperance movement's blood pressure.
I leaned over to the other bartender, a woman with a tattoo of a martini glass on her wrist. “What’s the story with this place?” I asked.
“Well, we call it a hidden bar, but it’s more of an open secret. Where 'Pour Decisions' are always welcome." The owner, Tommy Two-Tonic, started it after his last place, ‘Rum and Done,’ got raided. He figured if he kept things on the down-low-proof, he’d stay in business longer.”
“Doesn’t the law ever catch on?” I asked.
She laughed. “Nah, they’re too busy trying to crack down on that other illegal racket, pineapple on pizza. Besides, we're not breaking the law. We're just giving it a little liquid persuasion. We’re not just mixing cocktails; we’re mixing history with a dash of humor.”
Just then, a man burst through the door with wide eyes and a frantic energy. “The fuzz is coming!”
The room went silent. Then, like a perfectly executed pour, everyone moved into action. A series of bells, whistles and sliding panels could transform the speakeasy faster than you could say "bathtub gin".
The jazz band started playing and the bartender flipped a switch, revealing a secret room behind a bookcase labeled “Distill My Heart.” Patrons funneled through it with drinks in hand as though it were all part of the act.
I hesitated for a moment before following. “What’s back there?” I asked.
The bartender winked. “Another chapter in this spirited story.”
Inside, the room was smaller but just as lively, with drinks being served in teacups to throw off any nosy authorities. The walls were adorned with signs that would make the most serious federal agent smile, “Liquor? I Barely Know Her!”, "Serving Time, One Shot at a Time.", and "Our Spirits Are Always High (and Mostly Illegal)".
As I settled in, sipping on a new drink called 'Mint Condition,' I realized that this wasn’t just a bar, it was a movement, a place where people gathered to toast to freedom, humor, and a little dash of rebellion. A middle finger to Prohibition, wrapped in with, distilled in defiance and served with a side of shameless wordplay. "Prohibition? Never heard of her!"
In an era when fun was as prohibited as alcohol, they proved that the human spirit could not be bottled up, unless of course, it was a really good whiskey.
And if anyone asked where I’d been, I’d just tell them I was taking care of some 'Pressing Matters.'
Cheers to that.
Finding a speakeasy can be really cool as there’s a certain thrill of finding a hidden entrance or knowing the code or password to get in. Once there it’s the charm of ordering a craft cocktail or experiencing the intimate atmosphere. In some cases, speakeasies have a way of transporting us to another time. Part of the allure lies in the secrecy and unspoken rules. This includes speakeasy etiquette. Things have changed from historical speakeasies to modern speakeasies, but etiquette still applies.
Speakeasy etiquette first emerged during Prohibition in the 1920s. Drinking forbidden alcohol was an outlet for those opposed to new laws of banning alcohol. So discretion was the most important rule. Patrons had to be mindful of where they were and follow a strict code of secrecy.
Imagine what patrons had to go through to actually enter a speakeasy. You have to know where they are, you have to know how to get in and you have to know how to do so without letting others know. This might include finding an unmarked door, giving the secret knock and whispering the password through an open slot. It wasn’t just for effect, it was literally a matter of survival for each establishment. If you were one of the few who was actually lucky enough to gain entry, you’d experience what very few people did. You’d walk inside and find yourself in a small and intimate, smoke filled room with jazz music, dim lighting and the bar.
Before entering the speakeasy, the unspoken rules included no discussing the location with outsiders and no sharing of inside information.
Once inside, the unspoken rules continued. This included no loud conversations and no drawing attention to yourself. People went to a speakeasy to blend in, enjoy the music, and order forbidden drinks without making a scene. Even then, respect for the bartenders was paramount. They were not only mixing your drinks, but the bartenders were often the ones running the show.
It’s fascinating to think about how etiquette shaped the speakeasy culture back then. It wasn’t just about secrecy. It was about being part of an exclusive experience, where shared trust and respect were everything.
Today the stakes are lower, mainly because there are no raids and in most cases alcohol is not illegal. Modern speakeasies still honor many of these traditions and a sense of nostalgia. It’s what makes visiting a speakeasy so special. While the rules may have changed, the spirit remains the same.
One of the things you’ll notice about a modern speakeasy is the effort it takes to find it. Keep in mind, many speakeasy themed establishments, create an experience and gamify how to get inside. Most hidden bars aren’t trying to prevent people from entering, but they want to keep alive the secrecy to gain entry. They thrive on secrecy. Whether the entrance is behind a bookshelf, inside a phone booth, or hidden in plain sight. I’ve had the pleasure of hunting down several speakeasies in cities like Austin, New York City, Salt Lake City, Seattle, Lisbon, and more and finding the entrance is half the fun.
Once inside, it’s important to respect the speakeasy etiquette. Most speakeasies are intentionally small and intimate with dim lighting and vintage decor. Loud conversations or rowdy behavior are big no-gos. These places are designed for quiet enjoyment and not for shouting over a crowd.
Showing respect for bartenders is another key aspect of modern speakeasy etiquette. Most of them are skilled mixologists who take pride in their craft. They’re not just making drinks, they’re making experiences and creating art in a glass. The server or bartender will often share more on the drinks, so take time to appreciate their work. If you have the opportunity to have a conversation, ask questions and don’t be afraid to try something new. Some of my favorite craft cocktails were by simply asking the bartender to surprise me.
Phones also play a key part in speakeasy etiquette. While most speakeasies don’t necessarily ban phone use, it’s generally understood you shouldn’t use it there and if you do, keep it to a minimum. Take a quick picture without flash if you must, but don’t spend the evening scrolling or live-tweeting your experience. Part of the charm of a speakeasy is being present in the moment.
Here are my recommendations when visiting a speakeasy: 1. Dress nicely, 2. No large groups (keep your table size small and intimate) 3. Keep your conversations quiet (avoid being loud) 4. Enjoy the experience, so put your phone down and be present. At its core, speakeasy etiquette is about respect. Respect for the space, the people who create it, and the history it represents.
Ok, truth. So the first time I found out about speakeasies, it was through a TikTok that went viral showing some guy pushing through a bookshelf into a hidden bar in NYC. I was 22 and completely obsessed. Seven years later, I've become that friend who knows all the secret spots in almost every city and I literally travel to visit these speakeasies. But honestly, the whole scene has changed so much, even in just the short time I've been part of it.
Remember when everyone was posting those "secret" phone booth entrances on Instagram around 2018? That was basically my introduction to the scene. Now those feel almost cliché, but what's replaced them is so much cooler. Recently, I visited Cruise Room in Denver where you have to scan a QR code that leads you through an AR scavenger hunt just to find the entrance. The whole thing took about 15 minutes, but such a fun experience.
Growing up with social media, you'd think these places would have lost their mystery by now. I mean, nothing stays secret when everyone's posting their lives 24/7, right? But these spots have gotten crazy creative with keeping the magic alive. The best ones are constantly switching things up, like this hidden bar "Garage" in Austin changes its entire menu and concept every season. I love it! Last time I went, the theme changed, and we had to decode actual morse code messages to order certain drinks.
The drinks themselves have gotten wild too. We're way past the basic prohibition-era cocktails that were everywhere when I first started going to these places. Now it's all about the experience. One of the coolest was a cocktail that changed colors based on the temperature of your hands, and another came with an edible QR code printed on rice paper that unlocked a special AR filter when you scanned it. They're so innovative with the drinks.
What's really interesting is how these places handle social media. They know we're going to post. I mean, how could we not when everything looks so aesthetic? But they're super smart about it. This spot in Chicago actually has specific moments in the evening where they create these incredible photo ops, but then the rest of the experience is totally phone-free. They've even got these beautiful little lockers for your phone that become part of the experience. It's kind of nice, actually. Makes everything feel more special.
The crowd has changed too. It's not just millennials trying to relive the 2010s speakeasy vibe anymore. I see more Gen Z peeps, mixing with everyone else. We're all there for the same thing… something that feels real and special in a world where everything is usually so accessible and immediate. Plus, it's way more diverse than you might expect.
The best part about modern speakeasies is how they've adapted to our generation's love of gaming and interactive experiences. There's this place in Miami called Green Hat, is basically an escape room meets craft cocktail bar. Every drink you order gives you a clue, and if you solve the whole mystery by the end of the night, you get access to this super secret drink menu that isn't posted anywhere online. I still haven't figured it out, but it's so cool.
Speaking of which, it's kind of fascinating how these places market themselves, or don't. The really good ones don't even have official social media accounts. Instead, they build these whole mythologies through their customers' posts and word of mouth. Some use micro-influencers in really subtle ways, dropping hints about new locations or special events through seemingly random posts. It's like a real-life Easter egg hunt.
What I love most about today's speakeasy culture and scene is that it gives us something we're honestly kind of starved for. Genuine surprise! In a world where I usually know everything about a place before I even step through the door, these spots still manage to make me feel like I'm discovering something truly special. Sure, I'll probably post about it later, but for those few hours, it's nice to be somewhere that still feels like a real secret.
So yeah, maybe the original speakeasies of the 2000s would roll their eyes at our AR-enhanced, social-media-adjacent version of hidden bars. But I think we've found our own way to keep the mystery alive. In an age where everyone knows everything, we've managed to create spaces that still feel magical, even if that magic sometimes comes with a side of digital innovation. Just imagine what they'll be like in 10 more years.
Now, if you'll excuse me, I just got a mysterious DM with coordinates to what might be a new spot opening. Time to grab my friends and go hunting for the next big secret.
I was standing in what used to be New York's most notorious speakeasy, now a trendy coffee shop. I imagined the colorful characters who once talked and drank behind these walls. The more I researched the secret language of the prohibition era, the more I was fascinated by how an entire underground culture developed its own vocabulary.
The birth of speakeasy slang wasn't just about being trendy or hip. It was about surviving prohibition and the 18th Amendment which banned alcohol in 1920. The saying, “with change comes opportunity” was real and Americans didn't stop drinking, they just got more creative. Participating in illegal activities without attention from law enforcement led to an explosion of speakeasy slang.
The first example is the word "speakeasy". This term originated from bartenders telling patrons to "speak easy" when entering and being in the bar. It meant to keep their voices down. This was just the beginning of my research on speakeasy slang.
Other words and saying I ran across painted a vivid picture of life during Prohibition. This was "The secret code of the streets."
If you walked into a speakeasy in 1925, you might hear someone order "coffin varnish" which was a poor quality, homemade whiskey or order some "hooch" which was illegal alcohol. This is actually still a term we still use today. A "bone-crusher" wasn't a tough guy, it was just a doorman. And "greasers" were the corrupt cops who could be bribed to look the other way.
One of my favorite discoveries was learning that a "Cup of Joe" originated during this period. Though there are competing theories, many historians believe it became popular in speakeasies where patrons would add liquor to coffee to disguise their drinking. I read "Joe" might have referred to Joseph Daniels. He was Secretary of the Navy and banned alcohol on ships, leading sailors to drink more coffee. This was an interesting story, but I'm not sure I agree 100%.
Characters who populated these establishments had their own slang. A "big cheese" was the person in charge, while a "drugstore cowboy" was a well-dressed man who loitered around trying to pick up women. If someone was described as "ossified," they weren't turning to bone, they were just incredibly drunk. The lingo was catchy.
Some of my favorite expressions include:
- "Ankle" - means to walk like, "let's ankle to the joint"
- "Cat's pajamas" - something excellent or high quality
- "Beat one's gums" - idle chit-chat or chatter
- "Giggle water" - alcohol
- "Horn in" - to intrude, which still may be in use today
What strikes me most is how many of these terms have seamlessly integrated into our modern world. When we call someone a "wet blanket" or say something is "the bee's knees," we're using pure speakeasy slang. "Bank's closed", which means "no more kissing", might have fallen out of use, but "bail out" (to leave quickly) and "crash" (to fall asleep) are still popular.
The term "bootlegger" has evolved beyond its original meaning of hiding flasks in boot tops to become synonymous with any kind of smuggling. And when we talk about something being "ritzy" or "swanky," we're channeling the spirit of the hidden bar or clubs where such terms were born. I love the speakeasy slang! The speakeasy culture.
In researching speakeasy slang, I realized prohibition did more than create a network of illegal bars. It changed our language in ways that continue to live within us today. While the speakeasies of the prohibition era disappeared with the repeal of prohibition in 1933, their colorful vocabulary lives on. It reminds us of a time when simply ordering a drink required knowing a password and a secret door.
So, next time you hear a phrase like "what's eating you?" or hear someone called a "flat tire" (a boring person), remember, this lingo is a unique piece of American cultural history that was born in the shadows of hidden bars. A time when speakeasy slang started to catch on and yes, it still lives in us today.