Arnold J. Toynbee's dramatic shift in perspective on Judaism and Jewish history reveals both evolution and persistent tensions in his historical framework. Through personal correspondence with Toynbee from 1955 onward, coupled with analysis of his "Reconsiderations" volume and Edward T. Gargan's "The Intent of Toynbee's History," a complex intellectual journey emerges. As Toynbee transformed from "Hellene" to "Christian" in his worldview, he reconceptualized religion from a mere instrument of civilization to the ultimate purpose of historical development. Five fundamental disputes shaped this transformation: the historical uniqueness of Judaism, modern Judaism's classification within Syriac civilization, the controversial labeling of contemporary Jews as "fossils," Jewish integration with Western civilization, and the proposed Jewish destiny as ethical monotheism's missionaries. While Toynbee's later work shows marked improvement in understanding Jewish history and elevates Judaism among "higher religions," significant disagreements persist, particularly regarding Zionism and Jewish identity. His vision of a Jewish mission centered on universal prophecy, though philosophically rich, exemplifies the broader tension between particularistic religious identity and universalistic spiritual aspirations that characterizes modern Jewish intellectual discourse.