Prohibition was responsible for a number of unintended consequences, including acting as the catalyst for the rise of organized crime and a culture in which bootleggers and rumrunners were often more admired than reviled. The most successful bootleggers—as represented by F. Scott Fitzgerald’s fictional Jay Gatsby—accumulated great wealth, which granted these men entrée into high society.
Marni Davis points out in Jews and Booze: Becoming American in the Age of Prohibition: “Urban ethnic criminal occupations of the past, like arson, pimping, and robbery, carried an ugly social stigma for all but those most desperate for a ghetto-based model of ethnic self-esteem. Prohibition-era bootleggers, on the other hand, were often glorified rather than marginalized in urban society. The “glamorization of bootlegging,” Davis adds, made gangster culture seem chic and attractive to other young and ambitious urban Americans. “Gangster slang and style became a subject of fascination and emulation in popular culture, a development that obscured distinctions between moral and immoral behavior.” Suddenly, jail became the big house, someone killed by the mob was bumped off, detectives were gumshoes, and a criminal lawyer was a lip.1
Rumrunners posed and were accepted as heroes and patriots. None fit the bill as well as Captain Bill McCoy, known far and wide as “the real McCoy.” As the King of the Rum Runners and founder of Rum Row, he compared himself to John Hancock and other patriotic smugglers of colonial times. In his own account of his exploits, McCoy suggested that Hancock, who ran cargoes of liquor and other illicit commodities into the American colonies, “might stand as the patron saint of rumrunners.”2
A teetotaler himself, McCoy nevertheless fueled the Roaring Twenties by smuggling more than one million bottles of illegal alcohol from the Caribbean to New York. McCoy’s maritime daring and willful defiance of the unpopular Eighteenth Amendment and government authority made him a household name during the era and earned him a Robin Hood–like mystique with the American public—one that has survived into the twenty-first century. He was the “hero” of a 2012 American Public Television documentary and was a recurring character in Boardwalk Empire. Unlike others of his ilk, McCoy dealt in unadulterated spirits, giving rise to a new meaning for the old phrase for the genuine article, “the real McCoy.”*
McCoy was not alone as a provider of high-grade liquor or the only rumrunner to pen a memoir. In September 1923, Scotsman Alastair Moray set out from Glasgow to the United States on board the 187-foot, four-masted schooner Cask loaded with thousands of cases of fine Scotch whiskey. It took Moray months to sell his cargo, a feat detailed in his book The Diary of a Rum-Runner: “A great deal of the whisky sold here reaches the consumer as it leaves us, that is, if it is going to one of the good clubs, first-class hotels or any of the wealthier homes or good restaurants; all of them have their own private bootlegger or firm of bootleggers, who deliver the proper goods.”
Among the rumrunners were a handful of women who belied the long-held assumption of the Prohibitionists that women would stand as one in the fight against booze. The most notorious was an operator who called herself Spanish Marie, who took over her husband’s ship when he fell overboard in 1926 after excessive sampling of his cargo. She cut an image of a female pirate as she strutted about with a revolver strapped to her waist, a big knife stuck in her belt, and a red bandanna tied about her head. Spanish Marie was captured in March 1928 while unloading liquor on the beach at Coconut Grove near Miami, and was released on $500 bail on the plea that she must go home and take care of her babies. The bail was increased to $3,500 when investigators found the children at home with a nurse while Spanish Marie was drinking at a speakeasy. The record doesn’t show that she was ever tried.3
* Despite many claims to the contrary, the phrase “the real McCoy” was in common use with the same meaning decades before the birth of Bill McCoy. Eric Partridge in From Sanskrit to Brazil (1952), says that it dates from the 1880s and originated in Scotland, where it was applied to whisky, men, and things of the highest quality. The whisky was exported to both the United States and Canada, where people of Scottish origin drank the whisky and kept the phrase alive. That said, Bill McCoy certainly popularized the term. As Herbert Asbury wrote of him in The Great Illusion: “He bought and sold his own booze, sometimes in partnership with wholesalers in Nassau and in this country, but he had no tie-ups with the big bootleg syndicates and was notorious along Rum Row for selling good liquor and dealing fairly with the purchasers. He often boasted that he handled nothing but ‘the real McCoy.’ ”