This chapter examines the evolution of US–Russia relations from 1901 to the crisis in 1903–1905, when Russia and the United States found themselves in geopolitical conflict in the Far East, the “tariff war” fueled tensions in economic interaction, ideology came to impact official Russia–US relations, and large numbers of Americans mobilized in an anti-Russian campaign following a brutal pogrom (riot) in 1903 in Kishinev. This event, as well as the American “crusade” for a free Russia that peaked during the Russian revolution of 1905–1907, stoked the existing geopolitical and ideological crisis. The chapter demonstrates that the explanation for both the Russian Empire’s and the United States’ ambitions in the Far East can be found in the interaction of their foreign and domestic policies and explores the new frame of mutual perceptions established under conditions of conflict and visualized in political cartoons. During the first crisis both countries’ earlier multiplicities of images of the Other came to be replaced by dichotomous visions of processes across the Atlantic and the desire to use the image of the Other as a “dark twin” for their own political purposes.