In Chapter Four when introduced to Nick Carraway, Meyer Wolfscheim assumes that Nick is looking for "a business gonnection," but Gatsby tells him that he has mistaken Nick for someone else and that he is just a friend.
This mention of a business connection, a euphemism for a job with the underworld, informs Nick that Jay Gatsby is not the gentleman that he portrayed himself as earlier in this same chapter. In fact, this association with Meyer Wolfscheim, a man who has human molars for cufflinks, and who is rumored to have been involved in the "fixing" of the 1919 World Series, certainly casts doubts upon Gatsby's character. Further, Nick begins to think that the rumors of Gatsby's connection with bootlegging may be true because when Nick asks Gatsby why Wolfscheim is not in jail for the fraudulent scheme of "playing with the faith of fifty million people," Jay Gatsby replies nonchalantly, "They can't get him, old sport. He's a smart man."
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