After Gatsby introduces Nick to Meyer Wolfsheim, he leaves them alone for a few minutes while he disappears to make a telephone call. While Gatsby is absent, Meyer Wolfsheim praises him effusively, telling Nick that Gatsby is a "man of fine breeding" and "a perfect gentleman." He also confirms the story that Gatsby has told Nick about attending Oxford University. Indeed, Meyer Wolfsheim calls Gatsby "an Oggsford man" and asks Nick if he has heard of "Oggsford College ... one of the most famous colleges in the world." Before this meeting with Meyer Wolfsheim, Gatsby has been telling Nick stories about his past, and in this meeting, Wolfsheim very conveniently confirms many of those stories. Nick's meeting with Meyer Wolfsheim does, therefore, seem to fulfill Gatsby's intentions for it, in that Nick does not question the complimentary remarks that Meyer Wolfsheim makes about Gatsby.

While Nick's suspicions do not seem to be aroused by this meeting with Meyer Wolfsheim, the same is likely not true for the reader. Meyer Wolfsheim is presented as a somewhat peculiar and untrustworthy character and a rather unreliable character witness. He mistakes Nick for a friend of Gatsby's who is looking for "a business gonnegtion," and Gatsby quickly corrects Wolfsheim by exclaiming, "Oh no ... this isn't the man." This mysterious business connection sounds suspicious and perhaps not entirely legal. We also learn, later in the scene, that Meyer Wolfsheim is a gambler and "the man who fixed the World's Series back in 1919." The reader by this point might start to question why Gatsby is friends with such a character as Meyer Wolfsheim and what business exactly Gatsby is involved in. There are hints throughout the story that this business involves bootlegging.