The first American Nobel prizewinner in literature, Sinclair Lewis (1885–1951), is often considered a straightforward realist. However, he was so shocked by Hitler’s Machtübernahme in 1933 and by the rise of the Southern politician Huey Long that he published a cautionary tale with the telling title It Can’t Happen Here (1935). By its plot starting in 1936, the novel represents the subgenre of science fiction called near-future fiction. Thus, it is evident that Lewis, by his satirical account of the rise to power of the fictional politician Buzz Windrip, wanted to show that even a well-established democracy might fall prey to tyranny, a radically unfamiliar form of governance in the United States. This chapter first discusses Lewis’s take on the near-future genre and the makings of Windrip’s political takeover as against the shortcomings of liberalism and its champions in the novel. Then it compares and contrasts Windrip and Donald Trump, and the liberal ambivalence that helped them become presidents. Finally, a plea is made for a kind of civic liberalism that could safeguard American social cohesion and civility.