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==Prohibition and the early 1920s== On January 17, 1920, the [[Eighteenth Amendment to the United States Constitution]] took effect and [[Prohibition in the United States|Prohibition]] was enforced for the next thirteen years. The amendment prohibited the manufacture, sale and transportation of [[alcohol (drug)|alcohol]]ic beverages. Since the demand for alcohol continued, the resulting [[black market]] for alcoholic beverages provided criminals with an additional source of income. By 1920, Luciano had met many future Mafia leaders, including [[Vito Genovese]] and [[Frank Costello]], the latter a longtime friend and future business partner, through the Five Points Gang. That same year, [[Lower Manhattan]] crime boss [[Joe Masseria]] recruited Luciano as one of his gunmen.<ref>Newark, p. 22</ref> Around that same time, Luciano and his close associates started working for gambler [[Arnold Rothstein]], who immediately saw the potential financial windfall from Prohibition and educated Luciano on running [[Rum-running|bootleg]] alcohol as a business.<ref name="Stolberg119">Stolberg, p. 119</ref> Luciano, Costello and Genovese started their own bootlegging operation with financing from Rothstein.<ref name="Stolberg119" /> Rothstein served as a mentor for Luciano; among other things, he taught how to move in high society and to dress stylishly.<ref>Newark, Tim, p. 30</ref> Rothstein employed Jack Diamond as a bodyguard and an enforcer; Luciano often worked with Diamond.<ref>Newark, p. 32</ref> He started selling heroin smuggled in from Montreal.<ref>Newark, p. 36-37</ref> In 1923, Luciano was caught in a sting selling [[heroin]] to undercover agents. Although he saw no jail time, being outed as a drug peddler damaged his reputation among his high-class associates and customers. To salvage his reputation, Luciano bought 200 expensive seats to the [[Jack Dempsey]]β[[Luis Firpo]] [[boxing]] match in [[The Bronx, New York|The Bronx]] and distributed them to top gangsters and politicians. Rothstein took Luciano on a shopping trip to [[Wanamaker's]] Department Store in Manhattan to buy expensive clothes for the fight. The strategy worked, and Luciano's reputation was saved.<ref name="Pietruska page 202">{{cite book|last=Pietrusza|first=David|title=Rothstein The Life, Times, and Murder of the Criminal Genius Who Fixed the 1919 World Series|year=2011|publisher=Basic Books|location=New York|isbn=978-0465029396|page=202|url=https://books.google.com/books?id=A_46aa7xG0YC&pg=PA201|edition=2nd}}</ref> By 1925, Luciano was grossing over $12 million per year, and made a personal income of about $4 million per year from running illegal gambling and bootlegging operations in New York that also extended into [[Philadelphia]].<ref>{{cite book|url=https://books.google.com/books?id=25RIDwAAQBAJ&q=luciano+1925+12+million&pg=PT39|title=A Brief History of Gangsters|author=Brian Robb|year=2014|publisher=Robinson|isbn=978-1472110688}}</ref> In 1927, he started living at the Barbizon-Plaza hotel; living under the alias Charles Lane, he lived for a number of years.<ref>Newark, p. 39</ref>
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