The biddies take a little detour from their noble grapes series to discuss how prohibition and illegal alcohol to the American public basically made the mob. Tune in to learn more about Al Capone, Lucky Luciano and the other mobsters that helped keep America boozy while raking in MILLIONS.


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Britannica, Colombo Crime Family

The Mob Museum, Prohibition Profits Transformed the Mob

TLTC Blogs, Castellammarese War

Prohibition: The Mob Museum, Prohibition Profits Transformed the Mob

Brittanica, Al Capone Biography

Legends of America, Lucky Luciano

Zocalo, How to Drink Like a Gangster

PBS: American Experience, Why Did the Mafia Own the Bar?

Study Notes On Prohibition and the Mob:

*Please note these are the literal notes we created to record the podcast and sections may be copied and pasted from our sources above.

“A fleshy, widely plante, relatively early ripening member of the Bordeaux family”

Past Episodes of Note:

“The tie between booze and gangsters has been around since the early 1900s when mobsters started using dark and dingy bars to plot their crimes and hang out with fellow underworld denizens. But it was prohibition really cemented the relationship” (Scott M. Deitche – Zocalo


  • Before Prohibition started in 1920, members of criminal gangs in large American cities existed on the outskirts of society
  • A “social hierarchy” of big-city “bosses” existed since the 19th century
    • Political machines that financed the control of votes in their neighborhoods
    • Payments came from criminals running gambling and prostitution rackets then bribing police to look the other way
    • Under the bosses” were various ethnic groups (Irish, Italians, Jewish people, Polish) who focused on “street-level” crimes such as extortion, loansharking, drugs, burglary, robbery, and contract violence
    • This being said, the terms “organized crime” or “syndicate” really didn’t become popular until Prohibition and its aftermath
  • Prohibition practically created organized crime in America – the foundation was there but it truly built upon that
    • They already understood banking and other legitimate business and hard already been bribing policemen, judges, juries, witnesses and politicians for awhile
    • The greatest opportunity ever was presented to small-time street gangs: making sure Boozy Biddies and Spirits Studs had access to beer, wine and hard liquor
    • The profits were so enormous that gangsters learned to be more “organized” and employed lawyers, accountants, brew masters, boat captains, truckers and warehouseman plus armed thugs known as “torpedoes”
    • Bought empty breweries that close during prohibition & ran boats out into the oceans and lakes to buy liquor from Great Britain and Canada (rum running)
    • Prohibition created speakeasies
      • also referred to as “blind pigs” and “gin joints,” multiplied, especially in urban areas. 
      • ranged from fancy clubs with jazz bands and ballroom dance floors to dingy backrooms, basements and rooms inside apartments. 
      • Women allowed in speakeasies
    • Organized criminals quickly seized on the opportunity to exploit the new lucrative criminal racket of speakeasies and clubs and welcomed women in as patrons. 
    • The mob was behind supplying alcohol to basically all of the underground drinking operations
    • Speakeasies were generally ill-kept secrets, and owners exploited low-paid police officers with payoffs to look the other way, enjoy a regular drink or tip them off about planned raids by federal Prohibition agents.
    • Bootleggers who supplied the private bars would add water to good whiskey, gin and other liquors to sell larger quantities. 
    • Others resorted to selling still-produced moonshine or industrial alcohol, wood or grain alcohol, even poisonous chemicals such as carbolic acid.
    • The bad stuff, such as “Smoke” made of pure wood alcohol, killed or maimed thousands of drinkers. To hide the taste of poorly distilled whiskey and “bathtub” gin, speakeasies offered to combine alcohol with ginger ale, Coca-Cola, sugar, mint, lemon, fruit juices and other flavorings, promoting the enduring mixed drink, or “cocktail,” in the process. 
  • Bootleggers operated across the US
    • Detroit: The Purple Gang smuggled liquor on the Detroit RIver
    • Cleveland: Moe Dalitz’s Mayfield Road Gang used speed boats to ship liquor across Lake Erie from Canada
    • Largest syndicates were based in NY & Chicago
      • Both were port cities with considerable populations of immigrants for Italy, Ireland, Poland and other parts of Europe
        • NY: The infamous 5 families of NY (Gambino, Genovese, Lucchese, Bonnano, & Colombo) were born from Prohbition

Charles “Lucky” Luciano


  • Born Salvatore Lucania on November 24, 1897 in Sicily and moved to NY in 1906 at the age of 9
  • Constantly in trouble
    • Arrested for shoplifting at 10 years old
    • Got schoolmates to pay him 10 cents a week for their “protection”
    • Dropped out of school at 14 and was arrested multiple times for minor theft
    • By 1915 – a teenage hoodlum running a gang on the Lower East Side Of NYC and the Five Points Gang in Manhattan
  • Considered the main instigator of “modern American organized crime”
  • An Italian immigrant from Sicily was was 23 at the outset of prohibition when he began working for illegal gambling boss Arnold Rothstein (an important early investor in bootlegging)
  • By the mid 1920s, Luciano was a multimillionaire and New York’s top bootlegger working with Meyer Lansky, Benjamin “Bugsy” Siegel, Louis “Lepke” Buckhalter, and Abe “Longy” Zwillman
    • Also partnered with Vito Genovese (of the 5 families) and Frank Costello
    • At this point they all served the big boss Giuseppe “Joe the Boss” Masseria
    • In 1930 Masseria’s operation ran up against that of another boss, Salvatore Maranzano, for control of organized crime in NY’s Italian community. (fun fact: Both were considered “Mustache Petes” which were old world Sicilian bosses who did things very traditionally)
      • Engaged in a conflict known as the “Castellammarese War”
      • Castellammare is a town in Sicily and the birthplace of one of the most powerful bosses of Cosa Nostra (Sicilian Mafia) Salvatore Maranzano
      • This is recognized as pivotal in the transformation of Italian gangs in NY
      • This was a power struggle that left as many as 60 mobsters, including many high-ranking, dead
      • Lucky left Masseria to go to Maranzano who seemed “more flexible” because he was willing to bring in Lansky and Siegel who were both Jewish
      • In 1931 Lucky arranged for the death of his long time boss Masseria but then found out Maranzano was planning to kill him so he then had Maranzano killed making Luciano the undisputed leader of the New York Mafia
      • Rejected “boss of bosses”
      • Lucky had formed “the Commission” which was a criminal board of directors comprised of representatives from the recently sorted/created Five Families plus other leaders from other crime factions in the US including Al Capone
        • It’s purpose was to mediate disputes to serve as judges and executioners and to bring order to organized crime
  • By doing all of this, he became a very public figure and put on the radar or law enforcement so eventually he was arrested on June 6, 1936 and convicted of 62 charges of compulsory prostitution and sentenced to 30-50 years in state prison
    • This came after a raid on brothels and the connection to him
    • He was obviously guilty of much much more
    • Leadership of the commission went to Frank Costello


  • Luciano, “Bugsy” (Siegel) and Frank Costello went from simple robberies to selling illegal alcohol when Prohibition began in 1919
  • They soon supplied alcohol to all the Manhattan “speakeasies”
  • Luciano soon controlled plants, distilleries, truck and warehouses for illegal alcohol
    • His cohorts: Meyer Lansky. Bugsy Siegel, Guiseppe “Joe Adonis” Doto, “Waxey” Gordon, Vito Genovese, Frank Costello and Arnold “The Brain” Rothstein who had earlier fixed the 1919 World Series
    • Rothstein was the kingpin of the Jewish mob and took Luciano under his wing and educated him on running bootleg alcohol
  • By 1925, Luciano and his partners ran the largest bootlegging operation in NY
    • Imported Scotch whiskey from Scotland, rum from the Caribbean, and other alcohol from Canada

Al Capone & Johnny Torrio (The Outfit)

  • Al Capone one of the most famous American mobsters – born in Brooklyn along with Johnny Torrio who he later ran the Outfit in Chicago with
    • Always getting into trouble, dropped out of school, etc, part of “kid gangs”
    • Got slashed across the cheek with a knife or razor when he was about 21 – earned the nickname “Scarface”
    • Around the age of 21 he killed a member of a rival gang that was going to seek revenge so he was sent to Chicago to work for Johnny Torrio who was already over there working for brothel racketeer Big Jim Colissimo
  • Chicago based mob known as the “outfit” established by Al Capone and Johnny Torrio during prohibition
    • Torrio had Colissimo killed when he wouldn’t let him get into bootlegging (Capone may have been the one who did it)
    • The Outfit under Torrio, with Capone as his right-hand man, ran bootlegging, brothels and illegal gambling in the Windy City’s downtown and South Side. 
    • Torrio made deals with other Chicago gangs to share the spoils of bootlegging to avoid bloodshed. 
    • Gang shootouts flared during the Chicago “Beer Wars” from 1922 to 1926, when mobsters killed 315 of their own and police officers killed another 160 gangsters. The Outfit was a mostly Italian-American group that would fight violently in the 
    • 1920s with gangsters of Irish and Polish extraction, including Dion O’Banion, Hymie Weiss and George “Bugs” Moran, who controlled the illegal liquor trade on the city’s North Side.
    • The Outfit gunned down O’Banion in 1924. Torrio, nearly killed in a retaliatory shooting planned by Weiss in 1925, retired and turned over the business to Capone.
    • Capone made as much as $100 million a year (equal to $1.3 billion in 2016 dollars). 
    • At one point in the 1920s he paid out $500,000 per month (worth about $6 million today) to police to let him operate his illegal booze trade.
  • VALENTINE’S DAY MASSACRE + calls to end Prohibition
    • In 1929, seven of Moran’s associates were shot dead in a garage in Chicago during the storied St. Valentine’s Day Massacre. Moran, Capone’s target, luckily avoided the area moments before the shooting. 
    • Capone was immediately suspected of orchestrating the massacre, but never charged. 
    • The murders stunned the country, greatly eroded national support for Prohibition and influenced President Herbert Hoover to order federal authorities to “get” Capone. 
  • By 1930, Capone still ran about 6,000 speakeasies and made more than $6 million a week. 
  • But Capone finally met his downfall in 1931, when he was convicted of federal income tax evasion and sentenced to 11 years in prison.


  • Organized crime families owned the majority of the NYC’s gay bars and clubs
  • It was an unlikely but mutually beneficial association that lasted throughout the late 1960s
    • Even though homosexuality was legal in the state, most establishments that served gay customers were considered by the State Liquor Authority to be “disorderly houses” and were frequently raided by the police
  • The Genovese crime family in particular owned a majority of the gay bars in Greenwich Village
  • For example – the Stonewall Inn
    • Paid cops $1200 a month to stay away
    • Operated under the guise of a private “bottle club” 
    • Private clubs did not require a liquor license and they were not as easily entered or raided by police
    • The Inn required patrons to sign their name upon entry indication their membership but most were pseudonyms
    • With little police enforcement, Fat Tony, cut corners on safety, hygiene
    • No access to running water – potentially caused a 1969 hepatitis outbreak
    • Stonewall’s owners engaged in extortion – employees singled out wealthy patrons who were not public about their sexuality and blackmailed them for large sums of money which became the most profitable aspect of the Mafia’s club management
    • Even despite poor conditions and underhanded business tactics, there would not have been a “safe” place for they gay community to hang out so they tolerated it


  • Scotch and whiskey were always popular choices, particularly the whiskey brand Cutty Sark
  • Undercover FBI agent Jack Garcia said “Mobsters always order drinks by a brand. Never just a scotch and water, it would be a Cutty and water. And no one ever drank out of a straw”.
  • Mobsters would always get free drinks but loved to tip extravagantly so the drinks would end up costing more just because of the tips
  • “To them the best drink is the one you get for free”