Annals of work: Bootlegging in New York

In 1919 the federal government outlawed the manufacture, transport and sale of alcoholic beverages. Yet millions of Americans still wanted their beer, wine and distilled liquor, and they were willing to pay for it. A black-market industry emerged to meet the demand.

“Jean”—who declined to be identified further—had sold alcohol on the right side of the law before Prohibition. After it began, he crossed over and sold alcohol on the wrong side. The latter was more profitable, as illegal enterprises often are. He told his story in the mid-1920s.

When the prohibition law passed I was a waiter at Sherry’s. I became a naturalized citizen of this country twenty years ago, and although I tried to get in the army they turned me down because my eyesight was not so good. So I kept on through the war at Sherry’s and during those days saved up a very good bank account. People were spending right and left, and on the gay nights tips were high—men going to France, you know, and giving a party before they left. One  the last days before prohibition. a major gave me a thousand dollar bill. I owe it to my wife that I saved all the money I earned in those days. She would take it away from me and whenever I asked her how much the bank account was she just laughed at me.

But when prohibition came and the wine cards at Sherry’s were torn up, my income deteriorated. I told my wife we would have to use the money in the bank now, but she said that was to start us off in a business of our own and I couldn't have a penny of it. Pretty soon, without my knowing anything about it, she had started up a beauty parlor.

In the meantime, once or twice every night there would be somebody at Sherry’s who would ask me where to buy liquor. They seemed to think I ought to know and they would get mad when I told them I didn't know. You see there were a lot of rich young men who had never believed we would really have prohibition, and they had not bought up anything at all. In the first six or seven months of prohibition, everything was very dry. There was no bootlegging to amount to anything. People obeyed the prohibition law then more than they ever have since. But the young men who knew me at Sherry’s seemed to take it very hard. I just thought that prohibition law was the end of everything, and began to look around for something else to do.

One night about six or seven months after prohibition I went home as usual. But about three minutes after I had entered the apartment, the bell rang and a little fellow who looked like a jockey was standing there. He said he had followed me all the way from the restaurant so that we could have a quiet talk in my apartment. I asked him who he was, but he just laughed and said one of my very good friends had sent him to see me.

Well, what he wanted to say was this. He asked me if there were not a lot of my old customers who were anxious to buy something to drink. I had to confess that this was true. He said he thought so, and that he was ready to help me give it to them. I told him I would get in trouble trying to sell liquor at the restaurant, and he laughed again. That wasn't the way it would work, he said. I didn't know much in those days.

He went on to say that a friend of his had a large supply of liquors available, very choice stuff, and that he wanted some arrangement for letting the men who could afford to pay for it know about it. With that he stood up quickly and said he would be leaving. After he was gone, I found an envelope on the table with two hundred dollars in it, and a card with an address on Forty-sixth Street. On the card it was written, “Jean, drop around tomorrow.”

So the next day I went to the address. I had a long talk with a quiet fellow who said his name was Dolan. and the result of it was that I 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.

I visited during the next week about fifteen or twenty young men. And every one of them offered to take as much as I could bring them. It was fine stuff, and the prices were high. I received $150 a case for Scotch whiskey. Fifty dollars a case of that was my profit. But I had to have an automobile to deliver it, and so I conversed with my wife about selling the beauty shop. She wouldn't do it, but she agreed to get me an automobile, and the next day we went out together and bought one.

For about a year I stayed in this business, just delivering Dolan’s stuff among my customers for a nice profit. The police never bothered me and never seemed to bother Dolan. I did not know the source of his supply. But in those early days there were not many bootleggers and the police did not seem to bother much about them. I made good money.

As time went on, Dolan reduced his prices. He said it was foolish just to go after wealthy men. He said everybody wanted liquor and if the prices were brought down everybody would buy it and the business would increase. But it seemed to me that the quality of his goods began to deteriorate, and I was afraid to lower the prices to my customers for fear they would suspect something. As long as they were paying higher prices for their liquors than their friends, I knew they would think they were getting better stuff. And why not let them enjoy a little boasting? Anyway, I was not dealing in any poisonous hooch. It was real Scotch, just a little watered.

On my profits, I opened a little restaurant of my own about a year and a half after prohibition. I put a couple of barrels of wine in the cellar and sold it to my customers. I couldn't see any harm in that, and my wife said it was ridiculous to think that was breaking any law. But by now the police were getting on to bootlegging. The cop on the beat found out about my wine and started coming in for a bottle every night. That was all right, but when he started bringing all of his friends and going up to the cash register as if it was his place and taking out a ten or twenty dollar bill whenever he felt like it, I got tired of it. I told him to cease doing that. And he said he would put me in jail if I resisted him.

But I did not intend to give all of my profits to the police and their friends, so about six months later I just closed up the restaurant.

About this time I decided to branch out and go after a larger trade. I heard that a man named Immerman—he is dead now—was getting a lot of stuff from Rum Row and Cuba, good Scotch and high-priced cordials which were very rare.

I went to see him with a man who took me to a room over a garage in Brooklyn. In the garage I could see trucks piled up with all sorts of high class goods in cases. But Immerman told me that he was only running his goods in for a firm and could not do any business with me. I would have to see the firm in Times Square.

I went to this office and met the man who was introduced to me as the president. He would not talk until I told him to call up _____ ______, a famous Broadway spender that he knew would be all right. This man told him I was entirely reliable.

The president—I prefer not to mention his name—took me entirely into his confidence. And he made me feel like a piker sure enough when he told me what his company was doing. He said they had dozens of men like myself working on commission, or rather as agents, and that I could make a million dollars if I would help them with the disposal of their goods. He said their big problem was distribution.

He told me the firm could supply me with any kind of liquor that I needed for my trade in any quantity. He would guarantee me protection. And also, he said, he would show me how to expand my business so that I would only have to direct it and let other men do the work. I paid him one thousand dollars, which he said was a partnership fee and went into the lawyers’ fund. It was my first step toward really big business in the bootlegging industry.

Jean’s business was indeed really big. He concluded his story, and expressed no regrets.

I have made a lot of money. My wife handles all the cash, but I believe we have more than $100,000 invested in safe securities right now. I have never been arrested, and none of my men have ever been arrested except one, and his case never came to trial. I turned it over to the president of the syndicate, the man I have been paying $3,000 to $4,000 a year to, for “the legal fund,” and one day a lawyer called me to say the case was all over and never would be tried. I don’t know how they worked it, and I don’t care. I’ve been paying that much a year just to keep from being worried by things like that. . . .

I have gotten rich, but I have made a lot of people happy. I have never run across a man in my life who refused to take a drink because it was against the law, and I have never met a man who thought I was a crook, just because I am a bootlegger and proud of it.

From “A bootlegger’s story,” New Yorker, Sept. 25, Oct. 2, Oct. 9, Oct. 16, 1926.