"The Great Gatsby": a footnote
Halfway through F. Scott Fitzgerald's "The Great Gatsby", that classic 1920s novel of the immensely rich at play in their summer palaces on Long Island - the first darkly sinister note is introduced with the appearance of the mysterious Meyer Wolfshiem. This character is modelled on a real person: Arnold Rothstein.
Rothstein was already well-known in New York before the First World War as the "king of the gamblers"; a man-about-town with contacts throughout smart society. He then made a fortune from a racket involving war bonds, and was believed to have fixed the 1919 Baseball World Series (both these being referred to in "Gatsby"). But his real importance as the "Moses of the underworld" and original godfather of organised crime was still to come.
When Prohibition was imposed, Rothstein at once saw its money-making possibilities; but not for him the sordid peddling of rotgut homebrew: he thought on an altogether grander scale. In 1920 Rothstein's agents in Britain bought 20,000 cases of Scotch whisky and shipped them across the Atlantic. The documentation said the destination was the West Indies, but in fact the ship anchored off Long Island, where the cargo was transferred to a fleet of fast speedboats and run ashore on a lonely beach at dead of night. There a team from the Dockers' Union offloaded the booze into trucks, which drove through the country roads into New York. Rothstein had paid off the cops all the way along the route. Rothstein made eleven such runs before he was shot and killed in 1928.
Rothstein's operation would expect little trouble from the authorities: the main danger was from other criminals who might try to ambush and seize his supplies (the word "hijacking" was coined at the time for this very operation). So for protection Rothstein turned to the street gangs: to Owen Madden of the Gophers, to Benny Siegel and Meyer Lansky of the Broadway Mob, to rising young stars of the Mafia like Lucky Luciano, to psychopathic killers like Legs Diamond and Dutch Schultz. They provided Rothstein with muscle; he showed them how to make serious money and also taught them some much-needed social graces. This was the sort of operation for which a real-life Jay Gatsby would have worked.
Had Gatsby been a real person, his parties would surely have included the family of George Herbert Walker, a bucaneering businessman from the Midwest who had his own summer palace on Long Island. In 1921 Walker's young daughter met and married another rich young holidaymaker, but from a very different background: Prescott Bush. They became the parents of President George Herbert Walker Bush, and grandparents of George Walker Bush.
Walker was too old to be a model for Gatsby, and Prescott Bush would certainly have refused to have anything to do with bootlegging: he was a young man of high moral principles who later rose to be a Senator. Someone more likely to have been involved was a Catholic from Boston, of humble origins but rising to great wealth: Joseph Kennedy. Was he involved in operations of this kind? Almost certainly nothing can now be proved, but there have been occasional allegations. In the movie "Mobsters" (by far the most historically accurate film about the gangsters), the Rothstein character exclaims "Next year I lose my Scotch distilleries to Joseph stinking Kennedy!", and Richard Nixon is said to have complained of his victorious rival Jack Kennedy in 1960, "His goddam bootlegger father bought him the presidency!"
Rothstein was in reality quite unlike the ugly, uncouth Wolshiem of "Gatsby". Also, Wolfshiem is portrayed as a fairly small-time crook; but Fitzgerald could hardly have known about the vast scale of Rothstein's activities.
By far the best book on the subject is "Tough Jews" by Rich Cohen.