It was July 1929, and ex-convict Simon Walker walked into a speakeasy. He came with friends William “Red” Cassidy and Peter Cassidy, a couple of guys known as waterfront street fighters, and the bar was the Hotsy-Totsy Club at Broadway and Fifty-fourth Street. The speakeasy was owned by the gangster, Jack “Legs” Diamond, and his partner, Charles Entratta. Alcohol mixed with high tensions resulted in an argument between the Cassidy boys and Legs. Guns were drawn and shooting commenced. The orchestra played on, covering up the sounds of gunfire as Simon Walker was killed.
The murder of Simon Walker in the Hotsy-Totsy Club in 1929 was a common occurrence in the Prohibition days of New York City. Bootlegged liquor, speakeasies, and gangsters ruled the city, and the changing ideas of sexuality, class structure, and views on drinking turned the city upside down.
The Volstead Act went into effect January 1920, outlawing alcohol. It was the first time the government had attempted to control a moral principle in the citizens of the nation with the passage of law. Deemed the “noble experiment,” Prohibition sought to improve the lives of the poor by removing the vice of drinking. The noble experiment would be a colossal failure, and in no place would it be more spectacular than New York City.
Before Prohibition, saloons were the heartbeat of neighborhoods. Saloon owners were the first to raise money for patrons when an emergency happened or give loans until a patron could get back on his feet. Saloons were meeting places for unions and neighborhood groups. During the day when men were at work, mothers and their children would come to the saloons or children alone would be sent to pick up growlers for dinner, as the beer was safer than water to drink. The saloon was the first place an immigrant would learn how to manage the new world from those who had come before. Prohibition would end the idea of the saloon as a cultural center when drinking alcohol earned the glitter of being outlawed.
With the loosening of ideals around sexuality and drinking, speakeasies, cabarets and nightclubs flourished in a city that might not have even known of the Volstead Act if one just looked at the actions of its citizens. So enamored were the citizens of New York with this new, loose lifestyle, drinking became a sort of sport. While before Prohibition, it would damage one’s reputation to be arrested, being arrested for the violation of the Volstead Act became the cat’s pajamas. Members of high society would flaunt the fact that they had gone to jail for consuming alcohol, so neat was it to be caught drinking.
The nightclub evolved from the saloon as a way for establishments to slip under the radar of Prohibition agents. Such establishments would promote dancing as its main entertainment and not alcohol, just like cabarets. Using walnut or mahogany screens to shield windows, hidden doors inside other establishments, and even going so far as to move frequently, nightclubs and cabarets could offer the much sought-after alcohol while avoiding the scrutiny of the Prohibition Bureau. Even when speakeasies were padlocked for selling alcohol, the business would keep operating out of a back door, leaving the padlock in place as if the owners were abiding by the law.
Speakeasies became the place to see and be seen. They were often outrageously decorated with rich woods, glittering brass rails, and dazzling lights. The Aquarium even housed a giant fish tank. The Country Club had a mini golf course. The 21 Club became the exclusive haunt of midtown. Drinking was no longer a moral taboo. It was the center of nightlife in New York. People who had never drunk before were suddenly taking up the drink because it was the thing to do.
But this glamorous, carefree life came at a price. As liquor was outlawed, it was illegal to manufacture it, sell it, and consume it. Alcohol used in manufacturing was even poisoned to deter people from consuming it. They did anyway to dire consequences. But the speakeasies, cabarets and nightclubs had to find some way of getting alcohol for their patrons. This led to the extraordinary rise in organized crime in the 1920s. Bootleggers constructed elaborate rings to bring liquor into the city. The importers would hide their bootlegging businesses behind legitimate businesses like olive oil importing. The Menorah Wine Company even attempted to import over $100,000 in liquor on forged permits from the Prohibition Bureau under the guise of sacramental wine importation.
This organized crime had a little help from the inside. Prohibition agents were often unqualified for the job. Many were men returning from World War I and in need of a job. They would go into the bureau and start on the take from a gangster, earning more than they could ever dream. In return, the agent would tip off their gangster employer by calling from the bureau office the night of a raid. It got so bad the bureau turned off the phones in the office on raid nights. Agents would confiscate liquor from other bootleggers only to sell it to their gangster employers. A Prohibition agent was a great thing to be in the 1920s if you knew how to play your cards.
But it wasn’t just the gangsters of New York that were cashing in on this illegal trade. Ethnic groups, minorities, and new immigrants also found bootlegging as a way of just paying the bills and staying a breath above the poverty line. They would sell a shot of liquor out of a hip flask on the street, stand as guards in front of speakeasies to warn of raids, and set up shop as a “cordial,” where it was known liquor would be sold. In Harlem where unscrupulous landlords gouged rent prices, tenants staged rent parties near the end of the month, dishing out shots of liquor for high prices. They would collect enough to then pay the rent the next day.
But although the liquor was flowing and the jazz was roaring, the noble experiment caused a higher crime rate than ever before seen in New York City. Reputable businesses like the famed Delmonico’s were forced to close, and honest saloonkeepers forced out of business. It was with a reluctant heart that Franklin D. Roosevelt supported the wet movement in order to secure the democratic nomination in 1932. A dry from the beginning, FDR had no interest in repealing the Volstead Act, but popular consensus was against him. The noble experiment had failed. People were being killed for shots of liquor. Honest bartenders had been forced to carry out their trade in secret. Jobs were scarce, and the Great Depression loomed over it all. So when he took office in 1933, FDR stayed true to party platform and put into motion the steps that would end Prohibition. The roaring ‘20s were no more, and the sound of jazz faded into the night.
Lerner, Michael A., Dry Manhattan. Cambridge: Harvard University Press, 2007.
In the second grade, Jessie began a story about a duck and a lost ring. Two harrowing pages of wide ruled notebook paper later, the ring was found. And Jessie has been writing ever since.
Taking her history degree dangerously, Jessie tells the stories of courageous heroines, the men who dared to love them, and the world that tried to defeat them.
Jessie makes her home in the great state of New Hampshire where she lives with her husband and two very opinionated Basset Hounds.
Don’t miss To Be a Spy: A Spy Series Christmas Short Story. Find out more at jessieclever.com
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