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In 1904, Japan waged war against an ostensibly more powerful opponent, the Russian empire. A significant component in Japan’s victory was the financial support facilitated by Jacob Henry Schiff (1847–1920), an American Jewish banker who was born in Germany. Schiff has been described, in the context of the Russo-Japanese War, as primarily motivated by hostility to Russia, stemming from the tsarist government’s ill-treatment of its Jews. While this is certainly true, the case to be presented here is that Schiff’s motivations were diverse yet in his mind of one piece, and that as a prominent banker his diligence was rigorous in ensuring risks were mitigated. Additionally, Schiff’s unusually affirmative attitude towards Japan in the early twentieth century was at least as important in underpinning his actions, and perhaps an even greater counterweight, than his animus against an antisemitic Russia.