The first evidence exists in the extravagant parties that Gatsby throws with enough alcohol to cover the desires of an enormous crowd. Where would he find such access to quantities of alcohol in order to supply these parties every weekend? He must have had a connection to do so.
At the beginning of chapter 4, rumors swirl that Gatsby is a bootlegger—along with a murderer. People seem desperate to create a story for the man who keeps his personal information hidden. Later, Gatsby takes Nick to dine with Mr. Wolfshiem, whom he claims is a gambler who fixed the 1919 World Series. This doesn't directly condemn Gatsby himself, but since he does seem engaged in business dealings with the man, it casts a shadow on the type of business he is conducting.
The most condemning accusations come from Tom , who shares an acquaintance with Gatsby, Walter Chase. In a business deal, it seems that Walter took the fall for a bootlegging deal and went to jail for a month. This is seemingly where Tom has acquired...
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