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This paper will argue that pragmatist philosophy can provide important insights for analyzing the relationship between populism and democracy. Drawing in particular on the pragmatism of John Dewey, the paper will show that a pragmatist perspective is well-suited for explaining how the concept of “populism” could, over the course of the past decades, develop in novel directions and evolve into new meanings that have difficulty being harmonized with democratic principles. This pragmatist framework emphasizes how concepts can evolve in unpredictable directions due to unique circumstances, and so it can account for how the ostensibly democratic concept of populism could develop (under the circumstances of the twenty-first century) into a phenomenon based more on racial resentment toward minorities than on combating the exclusive economic and political power of wealthy elites. The paper will illustrate how Dewey himself aligned with “populist” causes of the late nineteenth and early twentieth centuries that combated such exclusive power, but also how in works such as Freedom and Culture (1939) he identifies how—under the conditions that led up to World War II—mass opinion could be channeled in ways that mainly generate aggression against vulnerable populations. In this way, Dewey’s pragmatism helps demonstrate the unpredictable forms that populism’s development can manifest, and illuminates our understanding of the relationship between older and newer forms of populism that have had varying levels of consistency with democratic principles.