
Meyer Wolfschiem [sic] is representative of Arnold Rothstein, the man who fixed the 1919 World Series in reality. His wearing of human molars for cufflinks is indicative of his crudeness and brutality, as the molars have been probably extracted from the mouth of one of his enemies.
Is Wolfsheim Jewish?
Carraway notes that Wolfsheim is Jewish, and as their conversation progresses, begins to suspect that he is likely involved in some disreputable forms of business. Caraway concludes that Wolfshiem is something of a shady character, which in turn, casts Gatsby in a murky light as well for his association.
Who is Meyer Wolfsheim?
Many interpretations of The Great Gatsby describe Meyer Wolfsheim as a direct analogy to the real-life individual known as Arnold Rothstein, kingpin of the Jewish Mob in 1920s New York. The most explicit link is that both are reputed to have fixed the 1919 World Series.
How does Caraway conclude that Wolfshiem is a shady character?
Caraway concludes that Wolfshiem is something of a shady character, which in turn, casts Gatsby in a murky light as well for his association. The second time that Carraway meets Wolfsheim is at the latter's office, towards the end of the story. Carraway has come into the city to ask Wolfsheim to come to the funeral of Gatsby, who has recently died.
Is Wolfsheim a major player in organized crime?
As an allusion to Arnold Rothstein, it is reasonable to conclude that Wolfsheim is a major player in organized crime in the story. As a friend and colleague of Wolfsheim, Gatsby also has achieved incredible wealth through bootlegging. It is how he affords to throw such lavish, booze-fueled, parties at his Long Island mansion.

Meyer Wolfsheim at the Speakeasy
The place where Carraway meets Gatsby and Wolfsheim is in a basement--an intentional choice of venue for being out of sight. Hidden away cafes and restaurants, known as speakeasies, were popular during the Prohibition Era because they were the only places people could be served alcohol.
Meyer Wolfsheim: Inspiration
The character of Meyer Wolfsheim was based on the real-life individual, Arnold Rothstein, a significant kingpin of the Jewish mob in 1920s, New York. This can be partially corroborated by comparing their last names, both incorporating traditionally Jewish suffixes.
Meyer Wolfsheim: Analysis
In The Great Gatsby, it is an understated fact that Wolfsheim is a successful bootlegger, someone who illegally transports and sells alcohol in violation of the National Prohibition Act. As an allusion to Arnold Rothstein, it is reasonable to conclude that Wolfsheim is a major player in organized crime in the story.
