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People suspect that Gatsby makes most of his money as a bootlegger, but he isn’t positively identified as such until the big scene in New York when he and Tom quarrel over Daisy. Tom has been investigating Gatsby and has learned some facts about him which he uses to try to destroy Daisy’s illusions. The most significant accusations are on page 133 in my edition of the novel.
“I found out what your ‘drug-stores’ were.” He turned to us and spoke rapidly. “He and this Wolfsheim bought up a lot of side-street drug-stores here and in Chicago and sold grain alcohol over the counter. That’s one of his little stunts. I picked him for a bootlegger the first time I saw him, and I wasn’t wrong.”
Gatsby doesn’t deny Tom’s accusation. Obviously Tom has gathered too much damaging information about him, and the more Tom talks the worse it seems to everyone present . Tom has found out that Gatsby, with Wolfsheim and others, is involved in other illegal activities.
The fact that Gatsby had bootlegging operations in the gangster-ridden city of Chicago makes him seem especially corrupt, because that city was known for mobster rule, criminals like Al Capone, and frequent murders.
It is found at the bottom of page 114, chapter 6. The quote is, "Who is this Gatsby anyhow?" demanded Tom suddenly. "Some big bootlegger?"
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