The Great Gatsby Questions and Answers
by F. Scott Fitzgerald

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In The Great Gatsby, why does Tom think Gatsby is a bootlegger?

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Tom thinks that Gatsby is a bootlegger because, as he says, he has "made a little investigation" into Gatsby's "affairs." He tells Daisy, Jordan, and Nick that he found out what was going on at Gatsby's "drug-stores" and that Gatsby has been selling grain alcohol illegally at these stores—this is essentially what it means to be a bootlegger. A bootlegger is one who illegally transports or sells alcohol during the Prohibition era.

Tom even claims that he had figured out that Gatsby was a bootlegger when they first met, though he does not explain how he knew this. He talks about the way Gatsby dresses as well as the big, loud parties that turn his house into a "pigsty," and it was likely the combination of these, as well as Gatsby's inability to understand the social cues associated with old money, that betrayed him and his humbler origins. How else could someone who wasn't born to money come into so very much of it so quickly if it weren't from something illegal?

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After the first of Gatsby's parties to which they are invited, it is clear that Tom begins to feel threatened by Gatsby and his lavish wealth. He makes clear his intention towards the end of Chapter Six to look into Gatbsy and how he so quickly gained such wealth and prestige. In Chapter Seven, it is clear that he now has that information, which he uses as part of their argument over Daisy whilst in the hotel during the blisteringly hot day. Tom says to Gatsby:

"I've made a little investigation into your affairs--and I'll carry it further tomorrow."

Thus it is that the investigator he has paid has told him precisely how Gatsby has made his wealth, and it has been by working with Meyer Wolfsheim and buying up lots of drug-stores where they sell grain alcohol over the counter.

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