This paper studies the life and thought of Kawakami Kiyoshi (1873–1949), a Meiji Christian socialist and prominent journalist in late 1890s Japan for the popular newspaper Yorozu chōhō (Complete morning report). Kawakami was one of the six founding members of Japan’s first but short-lived Social Democratic Party (Shakai minshutō, 1901). After the party was forced to dissolve under the Public Peace Police Law (Chian keisatsuhō, 1900) on 16 July 1901, Kawakami left for the USA to take up a postgraduate scholarship at the University of Iowa. While in the USA, he continued his career in the press, establishing himself as a well-respected international journalist. This paper focuses on his earlier thoughts, those developed during his “pilgrimage” to the USA from 1901 to 1907, during which his interests shifted from a gradual social reform to the issue of nascent anti-Japanese agitation in California and the question of Japanese immigration. During this time, he became convicted of the humanitarian ideals of Christianity and the values of sympathy and tolerance found in the chivalrous moral tradition. This journalistic period is under-explored in the literature and yet is essential in understanding Kawakami’s later role in US-Japan relations.