Meyer Wolfshiem is an underworld figure, who associates with gangsters such as
Rosy Rosenthal and is involved in various illegal activities. Gatsby tells Nick he is famous for having
fixed the 1919 World Series. His character was based on Arnold Rothstein, a real life gambler whom Fitzgerald had met. Wolfshiem clearly illustrates Gatsby has criminal connections as he knows Gatsby well.
It would be regarded as particularly reprehensible to fix a baseball game as this is regarding as the American sport. Nick says:
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.
While richly comic, the portrait may disturb readers of post-Holocaust generations as it mocks Wolfshiem's ethnic appearance with his
expressive nose and his Jewish accent:
a business gonnegtion. However, this anti-Semitic tone is endemic in many pre-World War II English writers from John Buchan, reaching back through Dickens to Shakespeare. All the upper-class characters in the novel are WASPs, who were considered the elite in the US at that time.
Wolfshiem provides a source of information about Gatsby to Nick (and the reader), filling in the missing details of Gatsby's rags to riches career path after the war. He is an example of the type of fair-weather friends who have surrounded Gatsby: after the shooting he initially refuses to speak to Nick and then subsequently declines to come to Gatsby's funeral. This reveals the selfishness and callousness of this kind of society.