The Great Gatsby

Jay Gatsby makes his money through illegal activities, especially bootlegging alcohol and organized crime.

At first, Gatsby presents himself as a self-made, wealthy businessman, but this polished story doesn’t hold up. His close association with Meyer Wolfsheim—a gambler famous for fixing the 1919 World Series—reveals that Gatsby’s wealth is tied to criminal networks. He speaks casually about Wolfsheim’s crimes and even admires his ability to avoid punishment, which links Gatsby directly to that world of corruption.

The truth comes out most clearly during the confrontation at the Plaza Hotel, when Tom exposes Gatsby’s business dealings. Gatsby and Wolfsheim have been buying up drugstores and secretly selling bootleg alcohol over the counter during Prohibition. In other words, Gatsby profits off the widespread illegal liquor trade of the 1920s.

Gatsby’s illegally earned wealth isn’t just background detail; it shapes his entire life. He builds his fortune specifically to win Daisy back, believing that money can recreate the past and make him worthy of her. But the way he earns that money ultimately undercuts his dream. The same corruption that makes him rich also makes him unacceptable in the world Daisy inhabits. The American Dream promises success, but in Gatsby’s case, achieving it requires moral compromise that destroys what he hoped to gain.