There is much debate concerning some of the characters in The Great Gatsby and whether they were drawn from real people. For instance, Meyer Wolfsheim is thought to be loosely based on popular Jewish Gangster Arnold Rothstein, whom you may know as a character portrayed in HBO’s Boardwalk Empire. Arnold Rothstein was the leader of the Jewish Gang in New York during the Twenties and is thought to have been involved heavily in organized crime, most notably gambling, and bootlegging. In chapter IV Fitzgerald introduces the character of Meyer Wolfsheim describing him as:
“A small, flat nosed Jew raised his large head and regarded me with tow fine growths of hair which luxuriated in either nostril. After a moment I discover his tiny eyes in the half darkness.” (69)
After Wolfsheim exits the scene Nick inquires who exactly he is suspecting that he is either an actor or a dentist. Gatsby replies:
“Meyer Wolfsheim? Not he’s a gambler.’ ‘He’s the man who fixed the World Series back in 1919.” (73)
The World Series mentioned of course is the 1919 Series between the Chicago White Sox and the Cincinnati Reds. Arnold Rothstein allegedly offered $100,000 to some 7-9 players to intentionally lose the World Series. A fact that Nick finds astounding in the novel saying:
“I remembered of course, that the World Series had been fixed in 1919, but if I had thought of it at all I would have though of it as a thing that merely happened, the end of some inevitable chain. It never occurred to me that one man could start to play with the faith of fifty million people—with the single mindedness of a burglar blowing a safe.” (73)
This character is interesting because it gives the reader real insight into not only the naivety of the narrator Nick Carraway, but also shows the type of people Jay Gatsby is in business with. Wolfshiem comes across as dishonest and crooked, which, in turn, directly reflects on Gatsby.
The connection of Wolfshiem and Rothstein is obvious, as Fitzgerald mentions him being Jewish and fixing the World Series, Rothstein’s claim to fame. But is Jay Gatsby also connected to the New York gangsters of the Twenties?