Generals Joseph W. Stilwell and Haydon L. Boatner shared extensive China experiences, starting from their tours in Tianjin to their roles as language students and US army attachés in Beijing in the 1920s to the 1930s. After Pearl Harbor, they returned to Asia to assume crucial positions in the China-Burma-India Theater (CBI). Chiang appointed Stilwell the commanding general and Boatner the chief of staff of the Chinese Army in India. However, American and Chinese officers clashed over command, in the training center in Ramgarh, India, and on the war front in north Burma. Boatner, often acting as Stilwell’s surrogate, became a lightning rod, drawing the ire of a number of Chinese officers. This chapter examines the contentious US-China relations as exemplified by Boatner’s conflict with his Chinese peers, especially during the Battles of the Hukawng Valley and Myitkyina. It cautions against interpreting Sino-American conflicts in moralizing, racializing, or orientalizing terms.