8 Fascinating Speakeasies that Helped the 1920s Roar

Larry Holzwarth - November 10, 2017

After the passage of the 18th Amendment made Prohibition the Law of the Land, legislation was required to establish the definitions of what exactly was being prohibited. The Dry faction in Congress, flush with their moral victory over demon rum, turned to a member of the Anti-Saloon League to draft the bill necessary to identify what was illegal and define the means of enforcing the new law. Wayne Wheeler was an attorney and a rabid supporter of the total prohibition of alcohol and wrote the new law under the sponsorship of the powerful Chairman of the House Judiciary Committee, Andrew Volstead. The Volstead Act, (which was vetoed by President Woodrow Wilson but the veto was overturned by Congress) became the impetus for the era of American History known as Prohibition.

It was soon clearly evident that the political shenanigans and blatant falsehoods which had led to the passage of the 18th Amendment did not reflect the opinions of the majority of American citizens. Politicians, judges, law enforcement personnel, veterans returning from the trenches of Europe, executives, laborers, farmers, clergy; a large representative majority of people from all walks of life opposed and blatantly ignored the new law. A new lexicon entered the American language; words like bootlegger, bathtub gin, blind pig, white lightning, hooch, giggle water, and many more colorful terms were soon overheard in everyday conversation.

While many preferred to take their illegal (and presumptively immoral) alcohol at home, others still preferred dressing up and going out to enjoy the conviviality of friends and music. Their destination, in cities all across the country, was defined by another new American word – the Speakeasy.

Here are some famous – and infamous – speakeasies from the Prohibition Era.

The Cotton Club

The Cotton Club opened in Harlem on Lenox Avenue at 142nd Street in 1923, as the enforcement of the Volstead Act was being reluctantly assumed by local authorities, many of whom were soon avid customers. Despite its location in a predominantly black neighborhood, the club was exclusively for white clientele, although it provided entertainment from the leading Black performers of its day.

Cab Calloway, Duke Ellington, Louis Armstrong, Count Basie, Billie Holliday, a young Lena Horne, and many others headlined shows during the Cotton Club’s glory days. Their audiences included luminaries such as George Gershwin, Al Jolson, Broadway composer Richard Rogers, Jimmy Durante, and frequently the Mayor of New York, Jimmy Walker.

The Cotton Club in the twenties was operated by Owney Madden, a bootlegger whom’s profession was not a secret. Perhaps because the Mayor was a regular customer the club had little trouble with the authorities. Shut down briefly in 1925, it soon reopened and Madden found his primary business – brewing beer and importing liquor – to be well supported by the club’s taps and bars.

Madden used his profits from the sale of smuggled Canadian Whisky to corner the market on local taxis and milk delivery routes. The milk, in particular, ar were useful in helping to establish a delivery service for his contraband directly to the door of his best customers. Madden hired a personal driver to convey him through the streets. This driver – George Raft – would later establish a Hollywood career portraying gangsters and bootleggers. Madden quickly expanded his club activities across New York, eventually owning all or part of twenty speakeasies and clubs.

The Cotton Club welcomed the end of Prohibition and continued operating as a legitimate club at the original location until 1936 when race riots led to its closing. It reopened in the Theater District later that year, but never achieved the notoriety of the glamour years of Prohibition when it was well known as one of New York’s most popular speakeasies.

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The Stork Club

Sherman Billingsley was a former resident of the federal prison at Fort Leavenworth Kansas when he arrived in New York with an eye for acquiring a chain of drug stores. Soon he was branching out and in 1929 he opened the Stork Club. Originally the club was a legitimate restaurant and nightclub in the front, where the display of secret hand signals would allow a patron, after passing the scrutiny of bouncers, into another room in the back.

In that room there was enough sin to cause a Temperance proponent to faint; liquor, gambling, dancing girls and something new to Prohibition – women drinking openly and freely in the company of men. For two years the club ran smoothly and without incident before the authorities raided the place in 1931.

Billingsley soon reopened the club on 51^st Street, and operations continued until an angry patron complained to the police over losing money in a defective slot machine (some say it was only a quarter). The police had no choice but to follow up on the complaint and during the ensuing raid, they demonstrated their “respect” for the owner by allowing the patrons at the time to pay their tabs, collect their illicit gambling winnings, and leave quietly, before locking the clubs doors. The club would reopen in 1934 after the demise of Prohibition and remain in operation until the 1960s.

During its Prohibition days, the club was a favorite stop for the denizens of New York’s theater world. Columnist Walter Winchell retained a table at the club throughout the illegal years, calling it the “…New Yorkiest place on West 58th Street.” The Stork Club was famous for its discretion during Prohibition, shielding its well-known patrons from photographers and rumor-mongers, and their response was to provide the needed money to ensure that the local police, and the occasional feds, looked the other way.

Billingsley retained ties to what was called “mob money” during the early years of the club before the largesse of his customers allowed him to separate the club and its operation from the growing influence of organized crime in the mid-1930s. In a side note, his daughter-in-law, Barbara Billingsley, achieved fame portraying June Cleaver – mother of the Beaver – two decades later.

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21 Club

New York’s venerable 21 was opened as a speakeasy in 1922, known to its neighborhood as the Red Head. Over the next few years, it moved often, changing names each time. By 1926 it was known as the Puncheon Club and catered to an exclusive clientele of patrons undeterred by the Volstead Act and its enforcers.

In the autumn of 1929 the club moved to the location, it occupies today and assumed its name as Jack and Charlies 21, Jack and Charlie being its two owners, always one or two steps ahead of the law. The number came from its address, 21 West 52nd Street.

Its frequent moves were always just ahead of or just after being visited by the prying eyes of the law. The club was raided frequently but managed to avoid the detection of illegal booze by either being warned by paid informers (or in some cases by customers who happened to work with the police), or a by an in-house use alarm system. In the event a raid took place without advance warning allowing the contraband to be hidden, a system of levers was activated which tipped the shelves and bars where the liquor was stored and consumed. The evidence slid down the shelves and into concealed chutes which routed it to the storm drains and sewers.

A hidden door concealed access to a storeroom which served to hold the club’s stock of liquor, and as a wine cellar. The door was in a brick wall, making its outlines difficult to see, and the room remains in use as a wine cellar today, with a portion of the room set aside for private functions.

The Stork Club throughout Prohibition had the reputation of serving high-quality imported (smuggled) liquor such as Scotch and Canadian Whiskey, rather than locally produced beverages of dubious quality. Then as now it was highly popular with New York and national celebrities. Babe Ruth frequently drank there and maybe the only person ever served hot dogs at the Club.

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The Green Mill

Chicago’s Green Mill holds a distinction which gives it a special panache among Prohibition-era illegal bars. It was one of Al Capone’s favorite places to spend an evening. Capone operated breweries all over the city and smuggled imported liquor from Canada, as well as operating several distilleries where low-quality “bathtub gin” was produced. But his preferred beverage was Templeton Rye Whiskey, which the Green Mill kept on hand for its most notorious customer.

As Prohibition wore on Capone’s men tried to muscle in on the Green Mill, including attacking a famous comedian and entertainer of the day, Joe Lewis. Lewis refused to perform at the Green Mill and for his temerity, he had his throat cut by a Capone henchman, although he survived the attack.

By the mid-1920s Capone’s rivals throughout Chicago made his whereabouts of interest whenever he was away from his headquarters and thus vulnerable. Beneath the Green Mill a series of tunnels were built, exiting to various points in the neighborhood. The tunnels provided several uses for the bootleggers; illegal liquor and beer could be moved in unseen by nosy law enforcement personnel on the street while bootleggers and their enforcers and cronies could exit the premises without using the street doors.

This was particularly useful in the event of a raid, incoming officers would find the illegal liquor – which was replaceable – but nobody to charge with its possession. Capone preferred a table which was near one end of the bar, through which was a hidden door leading to the tunnels and eventually to the street, where a waiting car and driver would whisk him out of harm’s way. Before he was forced to flee in such a less than dignified fashion Capone was often able to enjoy the entertainment offered by performers such as Al Jolson and Billie Holliday.

After Prohibition, the Green Mill suffered lean times and although it remained open it was largely known as a dive before a resurgence began with new ownership in the 1980s.

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Little Harry’s Speakeasy

The good people of Michigan were given a head start over the rest of the country imposing legally enforced prohibition of alcohol on their fellow citizens. Prohibition in Michigan began in 1917. Given its proximity to Canada, especially at Detroit where the bars, breweries, and distilleries were just across the river, it was always an iffy proposition enforcing complete temperance. Rival gangs quickly positioned themselves for dominance in the bootlegging trade, and the notorious group known as the Purple Gang achieved prominence.

The Purple Gang became strong enough to not only control the illegal market in Detroit but to occupy the role as a prime supplier of smuggled liquor to Al Capone’s Chicago Gang. Some scholars believe that up to 75% of all the illegal liquor smuggled into the United States during Prohibition crossed the Detroit River under the control of the Purple Gang.

All that activity was hard work, and even smugglers needed a place to unwind and perhaps consume some of their illicit products. Little Harry’s was a speakeasy where members of the Purple Gang could relax. It was located, according to recent excavations and research, at 624 3rd Street in Detroit, today the site of Tommy’s Bar.

Little Harry’s was in the basement of the building. It could be reached through an underground tunnel which may or may not have traversed a neighboring building. From there a staircase led below ground to a large room richly paneled in wood. Upon reaching the room entry was allowed after the presentation of a guest card; no card no entry.

The name “Little Harry’s” likely came from a man by the name of Harry Weitzman, who became the owner of the business above the bar in 1927 or thereabouts. That business remained open during Prohibition by selling soft drinks and avoiding any conflict with the law while keeping an eye on the less savory transactions occurring below. Weitzman had several business dealings with the Purple Gang before, during, and after Prohibition, and may have been placed in an ownership position of the legitimate business as a front by members of the Gang. Access to the false room below Tommy’s Bar is now bricked in, but portions of the tunnel remain as a reminder of the days when thirsty scofflaws went downstairs in search of an illegal libation.

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Rosslyn Hotel

The Rosslyn Hotel opened in 1914 at 5th and Main Streets in Los Angeles. Despite its 800 rooms, it was frequently full and in 1923, with Prohibition in full force, a 275 room annex was opened on the other side of 5^th Street, connected to the older building by a subterranean corridor. The corridor split a basement which contained barber shops, shoeshine stands and eventually a speakeasy known as the Monterey Room.

In the style upper-classes lounges of the day, a hat check room and reception desk greeted the visitor to the Monterey Room. Speakeasies were so common in Los Angeles that one newspaper of the day estimated there were more than 400 illegal bars operating in the city in 1919. Remaining hidden was of little concern.

Because of its distance to Canada and the professional fervor of government agents inspecting cargoes on ships arriving in the port at San Pedro, California speakeasies dispensed liquor of poorer quality than that of their northern brethren. Coupled with the new behavior of women accompanying men to bars – almost unheard of prior to Prohibition – bartenders needed considerable skill and inventiveness to arrive at new drink recipes – called cocktails – which masked the taste and texture of the cheap booze.

The access to fresh fruit, especially citrus, made California a leader in the development of many well-known and oft consumed cocktails today. Because of the sheer number of speakeasies and less well-heeled establishments known as blind pigs throughout Los Angeles, enforcement in the city was sporadic, and many speakeasies operated throughout the period without ever being disrupted by a raid.

At least twice Californians voted on statewide enforcement propositions and defeated them, and local support for enforced temperance was tepid at best, leaving the enforcement of the Volstead Act to the overextended federal government.

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Chumley’s

Leland Chumley opened his speakeasy on a corner lot in 1922 in New York’s Greenwich Village. A corner lot was particularly handy for an establishment devoted to the dispensing of illegal liquor. In the event that there should be unwelcome attention from the constabulary, a convenient second door on the side of the building provided the opportunity for rapid egress from the premises without running the gauntlet of incoming policemen.

Neither door leading into the establishment was marked, other than the address. Chumley’s rapidly became popular with the Village crowd, writers and poets, social activists and journalists, and other denizens of that famously eclectic neighborhood.

Chumley’s address (marked on one door) was 86 Bedford Street. The term “86”, meaning to discard something among restaurant employees, has been said to originate from the address. Leland Chumley paid protection money to co-operative local policemen (many of whom were devoted customers) and was rewarded with advance notice of an intended raid on the premises.

Reportedly one of the bartenders would answer the phone to hear the cryptic message to 86 the patrons and any visible booze, resulting in a quick emptying of the bar of patrons and products through the door bearing that number. The call signified the police would enter through the side door. Beside the side door, Chumley’s contained (and still contains) numerous hidden doors and connecting tunnels to allow for quick departure.

The side door, which opened into a small courtyard, was known to the patrons as the Garden Door. Both doors could be used for entry by customers in the know and known to the establishment. Chumley’s remained open long after Prohibition, always a favorite haunt of New York writers, and has recently been renovated. Perhaps in deference to its days as a speakeasy, both doors remain unadorned with signage, and customers desiring to enter must know exactly where they are going, as their forebears did during the Roaring Twenties.

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Cap’s Place

The citizens of South Florida were so disdainful of Prohibition that it would seem as if speakeasies were unnecessary. Rumrunners and bootleggers were rife and the police exhibited little interest in stopping them from completing their self-appointed rounds. When they did, the courts and juries were hesitant to convict. In one famous case, a New York real estate magnate (and bootlegger) named Harry Black was arrested with more than 50 cases of liquor stashed in his private railroad car. When bottles of the illicit liquor were used as evidence in his trial four members of the jury insisted on sampling them to ensure that they did in fact contain booze. The jury deliberated for less than ten minutes before Harry Black was found not guilty.

Regardless, some entrepreneurs opened blind pigs and speakeasies, and one such was Lighthouse Point’s Cap’s Unique. Cap’s was opened by Eugene “Cap’s” Knight, a former merchant mariner, sometime fisherman, and enthusiastic rum rummer. Cap beached a barge near a small inlet and erected a bar and gambling facility using the barge as a base. Because he was well known to the locals as “Cap” the establishment became universally referred to as Cap’s Place.

Cap’s was quickly popular as a gambling and drinking establishment and while it was well known for its illegal activities it was mostly left alone. Soon additional buildings were erected on the nearby shore, mostly for legal activities, though some were used to store additional liquor and other supplies.

Cap’s was reachable only by water, which provided additional security in the unlikely event that the authorities would attempt to curtail the fun. A thirsty hopeful would park near Hillsboro beach facing the speakeasy and flash headlights, in a previously agreed pattern. If the pattern was correct a small boat would emerge from the shadows of the barge and row ashore to collect the patron.

Nearby Hillsboro Inlet Lighthouse was used as a vantage point to ensure there was no encroachment by federal officers or the Coast Guard approaching by sea. The Lighthouse, manned by Cap’s brother Tom, would flash its beacon when unknown vessels got too near. Since 1990 Cap’s Place, formerly patronized by Al Capone, Meyer Lansky, Humphrey Bogart (while filming Key Largo), and more recently George Harrison and Mariah Carey, has been listed on the National Register of Historic Places.

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