What real-life gangster was Meyer Wolfsheim based on?

Meyer Wolfsheim was based on Arnold Rothstein, the real-life New York gambler and gangster. Fitzgerald’s fictional Wolfsheim is described as the gambler who fixed the 1919 World Series, a clear allusion to Rothstein’s reputation as the alleged mastermind behind baseball’s Black Sox scandal.

Rothstein, nicknamed “The Brain,” became a major figure in New York’s underworld during the 1910s and 1920s. He combined gambling, bootlegging, political connections, and financial influence, helping turn organized crime into a more businesslike enterprise. Fitzgerald had reportedly met Rothstein, adding a personal connection to the literary inspiration.

The novel does not state that Wolfsheim is literally Rothstein under another name; he is a fictional character shaped by Rothstein’s public image and legend. That is why the answer is sometimes phrased as “inspired by” rather than “based on.” The other choices were prominent gangsters, but none is associated with the 1919 World Series reference.