This article argues that certain interpretive trajectories within Jewish tradition – both halakhic (nomos) and aggadic (narrative) – can be illuminated vis-a-vis classical American pragmatism (CAP). Contrary to a prevalent belief, Peirce, James, and Dewey were neither anti-metaphysical nor anti-traditional. They contended, in different ways, that the ‘pragmatic maxim’ (PM) – “truth is what works” in James’s phrasing – is not a narrowly instrumentalist truth test. The PM rather implies that ideas and beliefs (philosophical and religious alike) should be examined against their worldly consequences. After a clarification of this relational idea in its pragmatist philosophical context, and an introductory sketch of the appearances of the PM in Jewish tradition, the article examines the PM within the thought of Rabbi Ḥayyim Hirschensohn (RḤH; 1857-1935). The article runs as follows: Section 1 presents CAP and clarifies what the PM is. Section 2 offers a bird’s eye mapping of the application of the PM within Jewish tradition. Section 3 briefs RḤH’s intellectual biography and elaborates on his pragmatist premises and his application of the PM. Rather than conceiving divine commandments as an arbitrary dictate, RḤH viewed them as purposive, relational, and as constituted and reaffirmed by individual and collective human agreements. Finally, the article reflects on the theological-intellectual prerequisites for the application of the PM.