Despite there being deep lines of convergence between the philosophies of Alfred North Whitehead, C. S. Peirce, William James, John Dewey, and other classical American philosophers, it remains an open question whether Whitehead is a pragmatist, and conversation between pragmatists and Whitehead scholars have been limited. Indeed, it is difficult to find an anthology of classical American philosophy that includes Whitehead’s writings. These camps began separately, and so they remain. This volume questions the wisdom of that separation, exploring their connections, both historical and in application. The essays in this volume embody original and creative work by leading scholars that not only furthers the understanding of American philosophy, but seeks to advance it by working at the intersection of experience and reality to incite novel and creative thought. This exploration is long overdue. Specific questions that are addressed are: Is Whitehead a pragmatist? What contrasts and affinities exist between American pragmatism and Whitehead’s thought? What new questions, strategies, and critiques emerge by juxtaposing their distinct perspectives?