The Great Gatsby

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The Prohibition created another opportunity for Wolfshiem to begin a brand new shady endeavor, which he ultimately hooked Gatsby into. Because alcohol was outlawed, it was harder to come by(obviously); however, in the 1920's you could get alcohol as a prescription drug and drug stores were allowed to carry it. So Gatsby and Wolfshiem opened up numerous drug stores together and made a profit by selling alcohol under the table. This is where all of Gatsby's wealth comes from (or so it's inferred), which enables him to throw the parties, which increases his "popularity", et cetera, et cetera...

Text retrieved on July 24th, 2013:

Despite the reality of the situation, overall it seemed like Americans were having a lot of fun during Prohibition. No book captures this wild and carefree time period quite like Fitzgerald’s novel The Great Gatsby. The character of millionaire Jay Gatsby represents the extremes of 1920s wealth and decadence. Gatsby devotes his life to accumulating riches in order to attract the attention of his romantic obsession, the lovely but spoiled Daisy Buchanan. Gatsby’s fortune is evident in the raucous parties he throws from his mansion on Long Island’s north shore. These decadent bashes, free flowing with food and liquor, represent the indulgent excesses of the “flapper” period:

“At least once a fortnight a corps of caterers came down with several hundred feet of canvas and enough colored lights to make a Christmas tree of Gatsby’s enormous garden. On buffet tables, garnished with glistening hors d’oeuvre, spiced baked hams crowded against salads of harlequin designs and pastry pigs and turkeys bewitched to a dark gold. In the main hall a bar with a real brass rail was set up, and stocked with gins and liquors and with cordials so long forgotten that most of his female guests were too young to know one from the other.”
- F. Scott Fitzgerald, The Great Gatsby

Gatsby character represents “new money;” he’s a seemingly overnight success with no known ties to family wealth. It is heavily inferred that Gatsby earned his fortune, at least in part, through bootlegging. How else could he afford his lavish parties with bottomless cocktails to spare? Daisy’s husband Tom gives voice to these suspicions during a heated argument, when he accuses Gatsby and his business partner Meyer Wolfsheim of illegally selling liquor through the drug stores they own. This fictional subplot is based in fact. For a small fee, doctors would prescribe their patients whiskey for just about any ailment, and sometimes no ailment at all. Crooked pharmacists would even sell forged prescriptions to their customers. As for Gatsby’s partner Meyer Wolfsheim, a character described as the man behind fixing the 1919 World Series, he was clearly influenced by a real gangster named Arnold Rothstein. The novel, at least in part, provides a reflection of the social issues and attitudes of the time period.