What It Was Really Inside A Speakeasy During Prohibition

"A Bootlegger's Story" appeared in The New Yorker in 1926, while Prohibition was still underway. The narrator offered an account of how he started selling contraband alcohol and gave a glimpse into the lengths it took to keep it all a secret. 

The Bootlegger was a waiter when Prohibition began and, after alcohol was banned, struggled to survive financially. He was constantly asked by patrons at the restaurant where he worked how to find booze and, at first, he didn't know. After several months, however, he was approached by a "little fellow who looked like a jockey" who had alcohol the Bootlegger could provide to his customers. 

By the end of the following day, the Bootlegger,

agreed to get the addresses of all my friends who came to Sherry’s, then quit my job and call on them at their homes.

Soon, the Bootlegger had several enthusiastic clients who paid $150 a case for Scotch whisky. The Bootlegger got $50 as his cut. After the Bootlegger had enough money, he opened a restaurant and sold wine there. It failed within six months because the police began extorting him for bribes. 

After his failed restaurant venture, the Bootlegger expanded to selling other kinds of alcohol through an unnamed organization. The key to making it a lucrative endeavor was to essentially lie to clients. Under the tutelage of another bootlegger named Immerman, the Bootlegger was told,

Of course, we are not delivering genuine Scotch liquor or genuine anything else. We cannot get that stuff any longer. We have fifteen or twenty big plants which are converting alcohol into whisky and wine and cordials and I had just as soon drink it as the real stuff. I will guarantee that it would not harm a child. But, of course, the customer does not like that idea. He likes to think that he is getting the real goods. And as long as the stuff we sell does not hurt him, it helps business to make him think so. So the main job is to make him think he is getting the real goods. He just enjoys it that much more.

To accomplish the ruse, the Bootlegger and his associates had a few nips of quality alcohol to provide as samples but, when it came time to deliver the goods, they'd been swapped for the lower-quality hooch.

New Yorker writer Lois "Lipstick" Long, for her part, indicated it was known the alcohol was less than high-shelf, recalling how "a chemical analysis" that appeared in a newspaper claimed the drinks were "near-lethal."

Al Hirschfeld, a caricaturist who wrote about the numerous establishments he visited in 1932, mentioned how varied the alcohol quality could be. Beer could be "needled" to some extent, meaning it was non-alcoholic beer or near-beer that had additional booze added back in, while finding higher and lower quality booze at the same place was common. It was just a matter of what an individual was willing to pay for. 

It was common for restaurant patrons to get liquor even without entering what one might call a speakeasy. Waiters became resources for getting alcohol and, in some establishments, trusted customers were served booze under-the-table from a hidden stash. This was common outside of major cities like Mount Carroll, IL. 

Mount Carroll was a dry city as early as 1908 and was well-versed in ways to avoid prohibitions on liquor by the time the Volstead Act went into effect. At a pool hall called Poffy's, owner Frank Poffenberger reportedly sold alcohol, only getting caught once:

In the back room the walk-in-cooler held a few gallon jugs of profit for the Poffenberger family. One visit from Sheriff Henry Shiley, unfortunately, cost the business about $700.

The Bootlegger also described "apartment barroom[s]" as a location where booze was sold in New York City. He mentioned "a former doctor who is running an 'apartment barroom'" - an establishment that ultimately got him thrown out of the medical profession. 

In cities, specifically, it was hard for individuals to run speakeasies, according to the Bootlegger. As a result, most speakeasies were "operated by syndicates." The Bootlegger explained,

It is necessary to have syndicates to avoid the padlocking danger. If a lone man is running a speakeasy, he is always in danger of being closed up. All he has to do is make a policeman mad, or fail to pay a prohibition agent as much as the agent thinks he deserves. And if he were running his business alone, his livelihood would be cut off.

In short, it was easier for a syndicate to pay off authorities and the like to keep the establishment running.

The Bootlegger provided an example to prove his point, too. He indicated that out of 32 establishments in one area that sold whisky, 25 were "owned by one firm... if one of the places is closed up, the rest keep right on doing business... and nobody lose much."

Getting access to the most popular drinking haunts was, according to Lois Long's The New Yorker writings, all about being in-the-know. She explained how it worked, first noting that places moved regularly among sites owned by the same person. Then,

by means of confidential head-waiters and captains, the crowd may be directed around and around the ring, delighting in new discoveries.

She continued,

This scheme is particularly successful with restless souls out to 'make a night of it.' No sooner have the waiters started to pile chairs on top of the tables preparatory to closing, than the same assiduous head-waiter begins to hint, 'The Wee Hours Club is opening about now, Sir. I could give you a special card if...'

Once the card was handed over, it meant visiting,

a converted brownstone, without outward and visible sign of the fresh couvert charge within. Many big dancing places maintain a whole string of these tiny places to make the hours between one and eight in the morning exciting. And the 'personally conducted' element is kept very well in the background.

Perhaps Frank Shay put it best in 1929's Drawn From The Wood: Consolations In Words & Music For Pious Friends And Drunken Companions. In that book, he quoted a minister who said:

If we had deliberately set out to increase drinking of alcoholic beverages, we could not have hit upon a better plan than prohibition.

Confirmation that booze was still in demand is found in the writings of Lois Long in The New Yorker. In 1940 she recalled that all Prohibition really meant was,

that the price of drinks went up two bits for a week or two and then returned to normal - normal being $1 a drink, $1.25 for a good drink.

This same idea is clear in every one of the descriptions offered by Al Hirschfeld. At The Bath Club, for example, 

The headier drinks are a dollar, which takes in the cocktail category. The wines are listed up to $40 the magnum and may be trusted.

For comparison, $40 in early 2026 was nearly $900. At The Press Grill, on the other hand,

The beer is a quarter and packs an instant kick of short duration. Brief vertigo after three of them. The hard liquor is fifty cents... the Scotch is authoritative.

There was a wide spectrum for what a drink could cost, but there's no indication people weren't willing to pay.