Uesugi Kiyoko (1270–1342) was the mother of the founder of the Ashikaga shogunate, Takauji (1305–1358), and his brother and chief administrator, Tadayoshi (1306–1352). Although Kiyoko lived within the vortex of a new political order that was being formed by her politically important sons in the early decades of the fourteenth century, little is known about her. Hers is a story not easily told: because information about her is so fragmentary, no monograph or even a single article in English or Japanese has been published about her life. In this essay, I seek to reconstruct the life of Uesugi Kiyoko through an examination of written records by contemporary diarists, personal letters, and poetry written by Kiyoko herself, and a number of physical sites relating to her life. The result is a nuanced picture of an educated woman who wrote letters and poetry, wielded significant land stipends in her own interests, and helped her two sons work together for political gain.