18 Details in the Daily Life of a Bootlegger During Prohibition

Transporting illegal liquor

Prohibition coincided with the rise of the affordable automobile in the United States, and cars became a valuable tool for the urban bootlegger. Less conspicuous than delivery trucks, the automobile provided opportunities for an enterprising bootlegger to move his product without fear of being detected by prying policemen. All that was needed was a little modification. Hidden compartments were created in trunks, inside doors, and in dashboards. A favorite modification was the removal of the rear seats and the installation of a compartment lined with cloth so that the bottles wouldn’t rattle.

The compartment was then concealed by a false seat cover, which was made to resemble the real seats with which the car was originally equipped. The delivery bootlegger picked up his product at a warehouse and delivered it to his customers without fear of detection. As much as ten cases of liquor could be concealed within the false seat, depending on the make and model of the automobile. Although many other models were used, the Ford Model T was a favored vehicle for several reasons. It was affordable, it was reliable, it offered a fair-sized hiding space, and it was ubiquitous, and thus less noticeable to the authorities.

As the sale of illegal liquor became more organized and syndicates developed, the bootlegger’s jobs became more specialized. The man delivering the booze was not the man selling it, nor the man collecting the money for it, but simply the man transporting it from the supplier. Security dictated the specialization. A bootlegger carrying both liquor and the money for it doubled the potential losses to the organization in the event that an honest policeman disrupted the delivery. Delivery men were valued for their driving skills and knowledge of the local layout, not for their ability to sell to customers or collect from reticent patrons.

Handling the authorities

In the early days of prohibition, some restauranteurs concealed barrels of wine, which can be made virtually anywhere undetected, in their basements or hidden storerooms. Trusted customers were made aware of the presence of the beverage, and given code words for ordering it when they dined. The restaurants also bottled the wine for its customers to take with them, and customers began to go into the establishments for the sole purpose of buying a bottle of wine. Their short time in the restaurant, entering and leaving far too quickly for the purpose of eating a meal soon drew the attention of the police.

In the early 1920s, policemen walked their beats and were known to the residents and businesses on a personal level. They quickly learned who was selling illicit liquor and wine, and in most cases became non-paying customers themselves. In fact, the officers often availed themselves of the alcohol and charged a fee for looking the other way. Those officers who tried to enforce the law were often denigrated by their peers, and faced demotion or transfer to more onerous duties.

Some officers in New York developed the habit of simply walking into an establishment which they knew sold alcohol and reaching into the till for a ten or twenty, defying the entrepreneur to say anything. In nearly all American communities, machine politics and the corruption of police forces were rampant, and the bootleggers took advantage of the corruption to establish ties to those running the police departments to protect their investments, and their customers, and curtail police harassment.

The bootlegger salesmen

As in many other businesses, such as cash registers, vacuums, brushes, and scores of others, the bootlegging syndicates employed salesmen to promote their wares. These salesmen carried samples with them, concealed often in compartmented cases which appeared at first glance to contain other products pertinent to the business they were visiting. A salesman visiting a restaurant might have carried samples of flatware or dishes, for example, or one visiting a drug store may carry patent medicines, concealing the booze beneath.

The bootleggers quickly learned that their customers wanted the genuine beverages which had been available before Prohibition, and their sample cases contained them. In reality, fine Scotch Whiskies were becoming increasingly rare and difficult to obtain. Smuggling did occur, on a grand scale, through Canada, and from Cuba. Smuggling brought with it inherent risks since it involved eluding the Coast Guard and the customs agents in the United States, and the Royal Canadian Mounted Police north of the border.

This meant that the salesmen often presented the genuine article for sampling and sale, but the delivered order was alcohol converted to resemble the real stuff with flavorings and coloring, presented in the appropriately shaped bottles and with genuine labels affixed to them. One New York bootlegger boasted that in his several years in the business he had never received a complaint regarding the quality of his products, none of which were the genuine article which his customers thought they were consuming.

The free-agent bootlegger

In restaurants and hotels, even so-called honest houses which officially complied with the law of the land, enterprising waiters, elevator operators, desk clerks, concierges, valets, and other employees acted as bootleggers independently of the syndicates. They purchased their liquor from other retailers, in smaller amounts, and offered it to customers by the drink in the restaurants and coffee shops, and sometimes by the bottle, with a profit margin added, to registered guests. These entrepreneurs often maintained a relationship with a nearby speakeasy, from which they received payment for referring customers.

The free agents, being independent of the syndicate, were outside of its protecting arm, though they frequently sold the syndicate’s products. It was up to them to bribe the local representatives of the law, either through cash or more often through free liquor to the neighborhood policemen. The policemen frequently responded by directing others toward the bootlegger in a mutually beneficial arrangement. Those in the know found that the coffee they had ordered was a shot of whiskey served in a coffee cup, or the glass of iced tea was in fact a Scotch highball. Scotch has a pungent smell, and the absence of detection indicates that the bootlegger’s employer was at the very least aware of the activity.

Free agents operated in barber shops, where daily visits of customers seeking a shave was not an unusual activity which attracted attention. The same was true of cigar stores, which in the 1920s were on nearly every city block. Cigar stores were also havened for illegal gambling with cards and dice in their backrooms, activities which predated Prohibition by decades, and which readily accompanied the new vice of illegal drinking. Cab drivers also found bootlegging to be a profitable enterprise, tacking on the cost of a quick drink to the fare, and receiving a larger tip for the service.

The Rum Runners

At the start of Prohibition, enterprising bootleggers sought product from sea captains which brought cheap rum from the Caribbean to ports in Florida and the Carolinas. The Coast Guard presence soon made it difficult for larger vessels to reach the coastline surreptitiously, and they began remaining just outside US territorial limits where they rendezvoused with smaller craft which would bring the rum ashore. The line became known as Rum Row. In 1924 an act was passed moving the territorial line to 12 miles in the hope that the smaller craft would be unable to handle the rougher seas further out.

Rum was bought cheaply, but it was also sold cheaply to customers and was thus a low-profit product for the bootleggers. Soon cheap English gin and sparkling wines from Europe were being transferred to Bimini and other points in the Bahamas relabeled as top-shelf London gin and either French Champagne or Italian Spumanti, and sold for high profits when they reached American shores. One rum-runner, Captain William McCoy, was said to have never watered his product, nor mislabeled it, leading his shipments to be referred to as “the real McCoy“, though the phrase has other origin claims as well.

Rum running meant dealing with the Coast Guard and the smugglers encountered the dangers of the sea, but the enormous risks involved brought tremendous potential earnings, with some of the more successful captains making over $100,000 a year. Most armed their vessels, and running gun battles with the Coast Guard patrol boats were not uncommon. The majority of the rum runners worked for specific bootlegging syndicates ashore, and many of the small boats which went out to meet the larger vessels were manned by bootleggers as well as professional fisherman and seamen, sent to protect their bosses’ investments.

Smuggling from Canada

While America went dry and its distilleries were closed, those of Canada continued to produce fine whiskies. In America, before prohibition, the favorite whiskey was rye, followed by Scotch, and bourbon’s appeal was limited to the south for the most part. During Prohibition, Americans developed a taste for Canadian whiskey. Bootleggers brought alcohol from Canada to the United States via the Great Lakes or moved it to the sea via the St. Lawrence River, where the ships carrying it joined the others on Rum Row, which became so crowded off of New Jersey, an important delivery point since it was near New York City and Philadelphia, that as many as 75 ships could be seen from the shore at times.

The ships on Rum Row, particularly those from Canada, offered further enticements to bootleggers to whom they wanted to sell their wares, including prostitutes who would provide free services to the bootleggers while their cargo was being transferred. Some ships flew banners advertising the beverages available for sale, and the prices. A Pacific Rum Row developed of the west coast of the United States, fed by ships from the western Canadian ports, and off southern California where South American rum was offered for sale to the bootleggers. The Gulf of Mexico was also crowded with shipping delivering products in demand by thirsty Americans.

As on land, where bootleggers were increasingly at war with their competitors by the mid-twenties, their sea-based fellows were soon in arms against each other in territorial disputes. Chicago’s Al Capone operated an important smuggling base on the island of Miquelon, a French possession near Newfoundland, and his ships left the island for rendezvous with the small craft armed with machine guns. Capone was just as determined to protect his water routes as he was his territory on the streets of Chicago, and just as ruthless in doing so.

A day at the office

As bootlegging syndicates grew, many of their heads became wary of dealing with individuals, as it was difficult and time-consuming to verify their credentials. Smaller firms developed, covering assigned territories, with the heads of the smaller firms operated them as if they were a legitimate business, with salesmen, delivery drivers, security, bookkeepers, secretaries, switchboard operators, and public relations offices. One New York bootlegger opened an office on Wall Street, and created an organization which ran so smoothly that he found he had little to do during the course of the business day.

He opened a second office in Times Square, and devoted his time to grooming special customers among the city’s business elite and political operatives. He groomed these gentlemen by first ascertaining their tastes and then providing gifts of expensive French brandies or fine Scotch whisky (The Scots, ever thrifty, spell the name of their beverage without the letter e) and once the target was within his debt, began selling it to them. The target soon shared his good fortune with friends, also those of wealth and taste, and a new customer base developed for the bootlegger, though he provided counterfeit beverages to them, because in his own words, “…his friends couldn’t tell the difference.”

The businessman bootlegger spent his day at the office calling friends and business acquaintances, dropping names, monitoring the books, schmoozing legitimate businessmen, supporting charitable causes, and conducting all the other affairs of business. In New York, lunch with fellow businessmen was often at 21 Club, itself a restaurant containing a notable speakeasy. At the end of the day, the bootlegger went home, or to another restaurant, or the opera or theater, often in chauffeur-driven Pierce-Arrow’s, Packard’s, or Cadillac’s, just another successful businessman and a pillar of society.

The wine bootlegger

The Volstead Act, the enforcement mechanism for national Prohibition, banned the manufacture, importation, transportation, and sale of alcoholic beverages. It did not ban consumption of alcohol, and it allowed households to make wine and cider for personal use. Ciders were produced in the apple-growing regions under this loophole and wines, particularly from California, were eagerly sought by east coast and Midwestern bootleggers, to grace the tables of their customer’s restaurants. California wines were not held in high regard by wine lovers of the day, so when they appeared in the eastern markets they bore French or Italian labels.

The California wines were blended with wine smuggled from Canada, which gave them some better flavor and aroma, though the bulk of the blend was the cheaper California wine. As with other beverages, the wine was bottled as if it were the real thing, and the blended mix would be labeled as if it were the product of European wineries of fine repute. Under the Volstead Act, up to 200 gallons of wine was allowed per household per year, and since grape juice could ferment to up to 12% alcohol in less than two months, wines became an inexpensive and profitable product line for the bootleggers.

The Volstead Act also allowed for private manufacture of ciders, with the same limit of 200 gallons, and cider manufactured legally was transported and sold illegally by the bootleggers. Formerly legitimate American wineries and cider houses managed to survive prohibition by continuing to press the fruit and selling the unfermented juices to customers, who took them home to ferment in their basements, in perfect accord with the law. Until, that is, the bootlegger took possession of the finished product, for which the wine and cider makers were paid, just as if they were an employee of the bootlegger, as many of them were.

The doctor bootlegger

Alcohol for medicinal purposes, most often whiskey and brandy, were allowed under the Volstead Act, as prescribed by a licensed practicing physician. In many rural areas, where bootleggers were less likely to be found easily, the doctor became the source of a desired beverage. Evidently, many Americans were concerned with their health during Prohibition, because between the onset of the ban on alcohol and the end of the 1920s, physicians earned $40 million dollars from prescribing alcohol for their patients, nearly one-half of a billion dollars in today’s dollars.

During Prohibition, prescriptions for alcohol were required to be written on a form provided by the federal government, the Internal Revenue Service of the Department of the Treasury. The completed prescription was taken to the pharmacist, where the form was canceled and the prescription filled. Both the pharmacist and the physician profited from the sale of liquor by prescription, and the records required intricate management to ensure that they maintained the appearance of legality. Because legitimate alcoholic beverages needed to be available in order to maintain its medical use, the government oversaw its production at a few distilleries.

Most physicians remained true to their oath to “…first do no harm” but the sizable number of alcohol prescriptions – more than three times the decade which preceded Prohibition, indicates that they were a bit more open-minded about its use for a variety of ailments. Doctors also maintained a stock of alcohol at their office or carried it with them on their rounds, enabling them to be a dispenser of good spirits in two senses of the phrase, completely within the boundaries of the law.

Disguising the fake liquor.

The bootlegger needed to go to great lengths to ensure that the deception of cheap homemade booze being sold as high-end liquor was successful. The high-priced liquor of Europe was elaborately packaged, and there were many pitfalls to be avoided when counterfeiting it successfully. One of the matters of least concern was taste, at least after Prohibition had been in place for a few years and the palate of American consumers became less discerning. Prohibition gave birth to the rise of cocktails, which though they existed before the ban on alcohol, known as “fancy drinks” became much more popular during the 1920s.

Some beverages had distinctively shaped bottles, which needed to be copied, and bootleggers provided American bottle manufacturers with samples, which were quickly emulated by the glass companies thankful for the work. Labels could be copied, but many bootleggers imported the real thing, usually from overseas counterfeiters. Corks required the stampings which were present on the genuine article, and the bootleggers hired corking companies to provide them. Scotch bottles were wrapped in straw before shipping, to prevent breakage, and some bootleggers went to the lengths of importing straw, which was of a slightly different color than that available in the United States.

Bottles were wrapped tightly in paper, soaked in salt water, and then dried, causing the paper to stick to the glass, an indication of a voyage across salt water, rather than manufacture in a warehouse in Bayonne, New Jersey or Cicero, Illinois. The cost of the deception was considerable, passed on to the customers who paid dearly for being sold goods both illegal to buy and counterfeit in nature. That bootlegger grew wealthy at the top of their organizational chains is an indication of the size of the demand for liquor by the American public, which grew throughout Prohibition rather than diminishes, despite the efforts of the government to quash it.

The Speakeasies

Nearly all of the speakeasies which operated in the City of New York, to cite just one example, were operated by the bootlegging syndicates. Even those speakeasies which were operated independently of the syndicates were as often as not selling alcohol provided by one of the syndicate partner branches, and when one was closed by a raid, the customers simply moved to another speakeasy nearby. The bootleggers needed to maintain some control in order to maintain their customer base.

One New York bootlegger wrote in 1925 that a single Manhattan cross street in the mid-40s between Fifth and Sixth Avenue, the length of a city block, contained 32 speakeasies and restaurants which sold whiskey and other alcoholic beverages to their customers. According to the bootlegger, twenty-five of them were owned by a single firm, which operated its businesses out of a Times Square office. As with most bootlegging firms, rents on properties were paid for at least one year in advance, in order to keep the landlord off the premises and to ensure that if the place was closed by a raid, there would be potential opportunities to reopen after the proper authorities were bribed.

The majority of bootleggers saw nothing wrong with their activities when it came to providing alcohol to their customers, despite it being flagrantly illegal on many levels. Instead, they saw themselves as providing a product and services which made their customers happy, in the face of significant personal and financial risks. Most of the independent speakeasies came to recognize that they faced serious risks on their own, and if their establishment was closed their livelihood was gone. As Prohibition wore on, the majority allowed their businesses to be absorbed by the syndicates, protecting them from unemployment and competition.

The apartment building bootlegger

Another type of bootlegger set up business in an apartment bar, usually in the building in which he resided. Two apartments were part of the scheme, near the top of the building, on separate floors. The upper floor apartment was used for the storage of liquor and was often listed under another name, a privilege for which the landlord was handsomely paid. The apartment below was furnished elaborately, with tables and chairs, settees and divans, and sometimes staffed by waiters who would serve food, cigars, and cigarettes, but no drinks. Only one or two bottles of liquor would be in the apartment at a time, kept in the kitchen.

When a guest arrived and ordered a drink containing alcohol, the bootlegger would invite him into the kitchen. Multiple guests were taken to the kitchen one at a time, served a drink, and then returned to the furnished guestroom to mingle with the other guests. In this manner, only two people were in the kitchen and saw the alcohol poured, the bootlegger and the purchaser. There were no other witnesses in the event that the apartment was visited by unwanted guests wearing police uniforms or carrying badges from federal agencies. In the event of a raid, all the police would discover was one or two partly empty bottles.

The apartment bootlegger sometimes operated out of hotels as well, known to the concierge, who was well tipped by the guests who wished to visit it as well as by the bootlegger operating it. Concierge service provided additional security, since the arrival of the police through the lobby would be noted, and upon arrival at the rooms the police would find the evidence disposed of and the guests dispersed. The apartment/hotel bootleggers were usually independent of the larger syndicates, who allowed them to operate because they were selling the liquor provided by the syndicates, and were easily moved about town if the authorities got too close.

Security

Nearly everyone in the bootlegging business, from the bottom man on the chain to the syndicate heads, paid for protection, from each other and from the authorities. The syndicates of course paid at the political level, obtaining protection from the local authorities by paying the heads of the political machines and chiefs of police. Federal officers were also subject to bribery. For the bootlegger, paying for protection was just another cost of doing business. Even the small-time independents paid their local beat cops for protection, and for referrals to their business. The beat cops were often used to direct customers to their liquid refreshment, for which they collected yet another gratuity.

The operators of the branch firms were given the names of local politicians or powerful businessmen, names which they shared with their employees, to be mentioned in an offhand manner when accosted by local authorities in compromising situations, such as being pulled over with a load of illegal hooch in the trunk. The mentioning of the name would not only end the inquiries of the arresting officer, but smooth the way along the rest of the miscreant’s journey, since the officer would phone ahead and warn other departments or precincts that a load of product belonging to so-and-so would be passing through.

The product itself was given innocuous names during these communications, such as those of soaps, with Ivory representing one type of liquor, and Lifebuoy another. Other products used included razor blades by brands, watches, clothing items (hats and spats were popular), and other commonplace items. Why such items were often moved in the dark of night at high speed was seldom if ever questioned, once the power of the protector’s name was invoked.

The moonshiners

Bootleggers preferred to manufacture their own alcohol or steal it from other bootleggers in order to hold down expenses, which as has been seen were considerable. But there was another source of illegal liquor available in the United States which had been illegal for years, manufactured mostly in the Appalachian Hills, by distillers trying to avoid taxes. It was high-proof liquor, distilled from corn and other grains, and could be cut with water and flavored to create other beverages, such as liqueurs and cordials. It was and is called moonshine, because the distillers often worked their stills under the light of the moon.

The large urban bootleggers were at their worst in Appalachia, desirous of the product, but unaware of the customs and traditions of the hills. After purchasing the moonshine it was delivered to shipping points by family members or friends of the moonshiners, if not the moonshiners themselves, paid for in cash. Once in the hands of the bootleggers it was shipped to their warehouses where it was used as the base for several different beverages which appeared in the northern speakeasies as Scotch, rye, bourbon, or even, if properly flavored, as brandies of various types.

Because it appeared on tables and bars as being something other than what it really was, moonshine did not become popular in the north during Prohibition, though much of it was sold there. The bootleggers did little, if anything, to extend their protections to the moonshiners, who often were forced to deal with local sheriff departments on their own, as well as the tax collectors with which they had always contended, known to them as revenuers. Although most bootleggers were forced to find other ways of making a living after the repeal of Prohibition, most of the moonshiners continued to distill illegal whiskey, as do many in the twenty-first century.

Capone

For the most part, it behooved a bootlegger to remain incognito, unrecognized in his profession other than by his customers. Not so for Al Capone. The syndicate which he built and which operated under his iron hand throughout most of Prohibition was one of the largest in the country. At one time he had over 1,000 employees, in Chicago of course, but also in Detroit, New York, St. Louis, and on the French islands below Newfoundland.

By the late 1920s, Capone’s syndicates were making, according to the Chicago Crime Commission, about $60 million annually. The violence associated with Prohibition is indelibly linked in the public mind to Capone, but he was involved in many other illegal rackets as well, including prostitution, narcotics, gambling, extortion, arson, hijackings, murder, and many others.

Capone built his criminal empire on bootlegging, and he paid his workers well, though he also disciplined them harshly. Still, though he never announced that he was a bootlegger, he did tell reporters that he “gave the public what the public wants.” The bootleggers that worked for him were under his thumb, and he gradually eliminated virtually all of his competition.

The woman bootlegger

Women were widely believed to be subject to more lenient treatment in the courts and by the police if arrested, and for this reason, many were recruited by bootleggers to serve alcohol at businesses frequented by women. Beauty parlors and tea rooms became places of resort for women who did not want to gain disrepute by entering a speakeasy unescorted, but nonetheless wanted a glass of wine or an alcoholic concoction.

Bridge parties and teas served at home became places where the bootlegger’s services and products were welcome, and with many women aghast at the idea of associating with so seedy a character as a male bootlegger, female bootleggers carved out their own niche, which expanded to diners and other businesses run by women.

Of course brothels, which were often frequented by the political powers of the cities and towns in which they were located, were a source of illegal alcohol as well, and nearly all of them were run by madams, who ran them more or less independently of the bootlegging syndicates, though it was from them that they obtained their product. The quality of the liquor served was one factor on which many brothels were rated, and the madams of some served the best liquor in town.

Confiscated bottled liquor facing destruction in March on 1923. Library of Congress

Life as a bootlegger

No matter where he or she stood on the supply chain, the life of a bootlegger was not an easy one. There were many hands to be greased, products to be monitored, officials to be dodged, and competitors to be dealt with. But for many bootleggers, it was a highly lucrative trade, and for the most part, one with upward mobility if one proved his ability on the job.

By the late 1920s the manufacture, transportation, distribution, and sale of liquor, all of which was against the law of the land, was the leading business in the United States according to some estimates, both in number of employees and in revenues generated. The loss of taxes collected by the government was one of the biggest factors in the repeal of nationwide Prohibition in the early 1930s. By then the country was mired in the Great Depression and the government needed the money.

In the many dry counties and communities which remained in the United States following Prohibition, the profession of bootlegger remains, seen in the moonshiners of Appalachia and elsewhere. They encounter the same risks and reap the same rewards as the bootleggers of the Roaring Twenties, providing a source for alcoholic beverages in regions where the powers that be are determined to protect people from their own lack of moral fiber and character.

Where do we find this stuff? Here are our sources:

“The Restless Decade”, by Bruce Catton, American Heritage Magazine, August 1965

“The Dry Decade”, by Charles Merz, 2017

“Prohibition: Thirteen Years that Changed America”, by Edward Behr, 1996

“Dry Manhattan: Prohibition in New York City”, by Michael A. Lerner, 2007

“A Bootleggers Story Part I, How I Started”, anonymous, The New Yorker, September 25, 1926

“The Rumrunners: A Prohibition Scrapbook”, by C. H. Gervais, 2009

“Prohibition: America Makes Alcohol Illegal”, by Daniel Cohen, 1995

“The Rise of American Wine”, by Paul Lukacs, American Heritage Magazine, December 1996

“Medicinal Alcohol”, anonymous, Ohio State University Temperance and Prohibition Page, OSU.edu

“A Bootleggers Story Part III, Methods”, anonymous, The New Yorker, September 1926

“Bar? What Bar?”, by William Grimes, The New York Times, June 2, 2009

“Last Call: The Rise and Fall of Prohibition”, by Daniel Okrent, 2010

“American Walks into a Bar”, by Christine Sismodo, 2011

“Said Chicago’s Al Capone: ‘I Give the Public What the Public Wants'”, by John G. Mitchell, American Heritage Magazine, February/March 1979

“The Hidden History of Women Bootleggers”, by John Grygo, UNLV Public History Online, November 4, 2016, online

“Deliver Us from Evil: An Interpretation of American Prohibition”, by Norman H. Clark, 1976