How did Gatsby acquire his wealth, and was it legitimate?

Okay, I understand. I will craft an essay, avoiding a point-by-point structure and explicit sequential markers, exploring the question of Jay Gatsby's wealth, its origins, and its legitimacy, suitable for an audience interested in both financial analysis and literary interpretation.
Here's the essay:
The shimmering facade of Jay Gatsby, a self-made millionaire throwing lavish parties in West Egg, Long Island, obscures a murky financial reality. F. Scott Fitzgerald's The Great Gatsby tantalizes readers with the spectacle of wealth but deliberately leaves the precise mechanics of its accumulation shrouded in ambiguity. Deciphering the source of Gatsby's fortune is crucial to understanding his character, his motivations, and the broader critique of the American Dream that Fitzgerald masterfully constructs.

Gatsby himself offers a vague, and ultimately, dishonest account. He claims to have inherited his money from his deceased parents, Midwestern farmers, but this fabrication crumbles under scrutiny. Nick Carraway, the narrator and Gatsby's neighbor, observes inconsistencies in Gatsby's narrative and detects an underlying discomfort when questioned about his background. This initial deception immediately casts doubt on the legitimacy of his wealth.
A more plausible explanation, one that gradually unfolds through whispers and indirect revelations, points toward a connection with Meyer Wolfsheim, a notorious gambler and businessman with connections to organized crime. Wolfsheim is presented as the man who "fixed" the 1919 World Series, a scandal deeply embedded in the public consciousness of the era. The implication is clear: Gatsby's association with Wolfsheim suggests involvement in illicit activities.
Specifically, Gatsby's wealth likely stemmed from bootlegging, the illegal production and sale of alcohol during the Prohibition era. The period from 1920 to 1933 saw a surge in organized crime, with fortunes being made through the black market trade in liquor. Gatsby's ownership of drugstores, a common front for speakeasies and alcohol distribution networks, further strengthens this hypothesis. He speaks of "certain business" ventures, often conducted in secret and involving questionable characters. These clandestine operations, coupled with the historical context, make bootlegging a highly probable source of his vast wealth.
Another potential avenue for Gatsby's financial success could be stock speculation and other risky investments. The roaring twenties were a time of unprecedented economic expansion, fueled by a booming stock market. While not inherently illegal, aggressive and unethical trading practices were rampant. Gatsby's eagerness to acquire wealth quickly, his willingness to associate with morally ambiguous individuals, and the overall atmosphere of unchecked speculation suggest that he may have engaged in risky financial maneuvers to bolster his fortune. The story hints at him having inside information or playing the market in ways that would have been considered ethically dubious, even if not outright criminal.
The question of legitimacy, however, extends beyond merely legality. Even if Gatsby’s wealth could be traced to technically legal, albeit morally questionable, investments, its origins remain deeply tainted. His wealth is not earned through honest labor or genuine merit; it is built upon a foundation of deception, exploitation, and ultimately, a desperate attempt to recreate the past. His pursuit of Daisy Buchanan is inextricably linked to his financial success. He believes that acquiring wealth will make him worthy of her, erasing the social and economic barriers that once separated them. Therefore, even if legally obtained, his wealth is illegitimate in the sense that it is used to pursue an unattainable and ultimately destructive goal.
Furthermore, the lack of transparency surrounding Gatsby's wealth highlights the inherent corruption of the American Dream itself. Fitzgerald critiques the idea that material success alone can guarantee happiness or fulfillment. Gatsby’s relentless pursuit of wealth, fueled by a desire to recapture a lost love, ultimately leads to his tragic demise. His wealth, obtained through questionable means, becomes a symbol of the hollowness and moral decay underlying the opulent facade of the Jazz Age.
Ultimately, the exact details of Gatsby’s financial dealings remain deliberately vague. This ambiguity is crucial to the novel's thematic resonance. Fitzgerald is less interested in providing a precise financial ledger than in exploring the moral consequences of unchecked ambition and the corrosive influence of wealth on individual character and societal values. Gatsby’s wealth, regardless of its specific source, serves as a potent symbol of the illusory nature of the American Dream and the enduring power of the past to shape the present. Whether derived from bootlegging, shady stock deals, or a combination of both, its inherent illegitimacy underscores the tragedy of a man who believed that money could buy him happiness and rewrite his history. The unanswered questions surrounding its origin only amplify the poignant commentary on the corrupting influence of wealth and the elusiveness of true fulfillment.