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Taking the paradigm of a bridging of "Orient" and "Occident" as a point of departure, this essay illustrated some of the ways in which Abraham Shalom Yahuda mediated this perceived divide, as he stood at the intersection of multiple and often conflicting scholarly and ideological movements and alliances, including Wissenschaft des Judentums, Sephardism, Zionism, and loyalty to the British Empire. Through discussion of his interactions with Jewish and Spanish scholars, leaders of the Zionist movement, and British colonial officials, this essay demonstrates how Yahuda profitably engaged in these relations, as he merged his sensibilities from the world of powerful Sephardi oligarchs in late Ottoman and early Mandatory Jerusalem and what has been rendered the "politics of notables" of the late Ottoman period with an Orientalist scholarly orientation. Yahuda's assimilation of the expectations others had projected onto him as a "good Oriental turned Occidental" shaped his self-fashioning, as it allowed him to fluidly move in and out of different milieux; yet this also complicates our understanding of his process of de-Orientalization to which others had alluded. I demonstrate that Yahuda was not "de-Orientalized" but was in fact very much caught up in the scholarly Orientalism and the ongoing imperial politics of his time. Ultimately he was unable to broker various imperial tensions and divides along the Oriental-Occidental axis.