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Meet New York's Most Colorful Prohibition Agents: A Tale of Grit

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Chapter 1: Prohibition's Unlikely Enforcers

In 1919, the ratification of the 18th Amendment to the U.S. Constitution marked the beginning of Prohibition, banning the production and consumption of alcohol. This legislation was widely unpopular across the nation. A significant factor behind its enactment was the influence of the religious movements of the time, which argued that a dry nation would lead to improved morals and reduced societal unrest.

New Yorkers, however, were discontent with the prohibition of alcohol. As a result, speakeasies began to flourish throughout the city. Although police were expected to enforce this law, many officers chose to ignore it, and some even accepted bribes from speakeasy owners.

Frustrated by the rampant disregard for the law, authorities sought new agents to enforce the Prohibition Act and target bootleggers. One of the first applicants was Isidor "Izzy" Einstein. At first glance, he did not fit the typical profile of a law enforcement officer; he had no prior experience or training, appearing as an everyman.

Despite his lack of qualifications, Izzy was determined and motivated. Struggling to support his wife and four children on his postal clerk salary, he saw the role of Prohibition agent as a chance to improve his circumstances. He argued that his unassuming appearance would work to his advantage, as speakeasy operators would not suspect him of being an agent.

Reluctantly, law enforcement leaders agreed, and Izzy Einstein was appointed as the first Prohibition agent.

One of Izzy’s initial tasks involved raiding a speakeasy in Brooklyn. According to procedure, obtaining a warrant required evidence of illegal activity, but most bouncers denied entry to law enforcement agents, fearing arrest. Izzy’s argument that he could gain access more easily became appealing. When he approached the Brooklyn speakeasy, he informed the doorman that he was a Federal Agent, prompting laughter from the staff who thought he was joking.

As Izzy persisted in asserting his identity as an agent, he was allowed inside. The doorman continued to laugh at him, sharing his claims with others in the bar. To demonstrate his authenticity, Izzy showed his badge, which only elicited more laughter from the crowd, who thought it looked fake.

During this first bust, Izzy learned a crucial lesson: he could not partake in the very evidence he was collecting. This hindered his case, leading him to devise a method for concealing alcohol in a small container within his coat.

Though he enjoyed his job, Izzy grappled with the morality of the law he was enforcing. He often discussed these conflicting feelings with his friend Moe Smith, trying to convince him to join as an agent as well. Eventually, Moe relented and partnered with Izzy, leading them to brainstorm various disguises to facilitate their undercover operations.

For instance, they once visited a liquor-serving restaurant near Mount Sinai Hospital, appearing scholarly with thick books and white coats. The bust was executed swiftly and efficiently.

In another escapade, Izzy braved the cold in a sleeveless shirt, prompting Moe to carry him into a speakeasy and request a drink for his shivering friend. This resulted in a mass arrest when the waiter complied.

On one occasion, Moe disguised himself as Izzy's wife to gain entry into a downtown speakeasy, leading to another successful bust.

Their elaborate antics often drew media attention, as reporters vied to cover the duo's escapades. Recognizing that Monday’s front page had more space, they scheduled their more outrageous raids for Sunday afternoons, ensuring favorable press coverage.

Izzy and Moe became celebrated figures for their successful raids, even earning respect from speakeasy employees for their cleverness and kindness. However, their superiors in the bureau were less amused by their public persona. Complaints arose regarding their ability to garner media attention, a talent that few other agents possessed.

Despite their success, Izzy and Moe's refusal to accept bribes from speakeasy owners led to increasing tension with higher-ups in Washington, D.C. In 1925, a decision was made to terminate them along with 34 other agents in what appeared to be a system-wide purge. Their impressive record of 4,932 arrests stood in stark contrast to the reason for their dismissal.

After their law enforcement careers ended, Izzy and Moe transitioned into selling insurance. They utilized the skills acquired during their time as Prohibition agents to educate potential clients on the necessity of insurance policies.

Eight years after their departure from the bureau, the Prohibition era concluded with the repeal of the 18th Amendment, allowing alcohol to flow freely throughout the nation once more—this time, legally.

The first video explores the impact of Prohibition and features a teacher’s reaction, providing insights into its historical significance.

The second video delves into the life of Al Capone, revealing intriguing connections and stories, including the surprising fact about his brother's profession.

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