This chapter explores Robert Herrick’s Memoirs of an American Citizen (1905) and its distinctive elements within the larger emergence and development of the American business novel genre at the turn of the twentieth century. Herrick’s novel uses Chicago – a city representative of the country’s emerging economic growth and social disparities – as a canvas to chronicle the rise of its archetypal businessman, the influence of its powerful business and political elites, and the capitalist ideology that sustained them, while at the same time questioning the lack of social responsibility in a market-driven economy. The chapter traces how Herrick, as a traditionalist and reserved writer from New England, ventured into the business novel genre to ingeniously depict in Memoirs a psychological portrait of a businessman, which is both compelling and troubling, and an authentic representation of Chicago’s economic landscape filled with opportunity and excesses. The tropes of the personal search for economic improvement and the desire for business success explored in Herrick’s novel remain as topical today as when they were first conceived.