The past few decades have witnessed a growing concern to reveal the futility of the quest for absolute, ahistorical rational standards. Instead, philosophers have sought theories that will prove responsive to the humanness of rationality. The classical pragmatist tradition in American philosophy provides a tremendously fruitful yet still too often overlooked framework for accommodating, clarifying, and extending current explorations of human reason. To present the pragmatic turn from transcendental reason to engaged intelligence in a way that emphasizes the magnitude of their break from the philosophic tradition while correcting standing prejudices, it is helpful to turn the spotlight on James. This essay sketches several interrelated claims about James's notions of reason and truth: Reason is embodied, evolving, and practical, and as such it is subject to physical, conceptual, and historical constraints. Further, reasoning is contingent upon perspectives and is characterized by an educated aesthetic response that can emerge from trust in a situation's potentialities.