The aim of the present article is to examine the historical development of the Tsuruoka Hachiman Shrine (present day Kamakura, Kanagawa Prefecture) during the Muromachi period, a subject that has not been given serious attention from the time of the compilation of the History of Metropolitan Kamakura: Temples and Shrines in 1967. This article focuses on the Buddhist abbots (betto 別当) and monks (guso 供僧) who served the Shrine during its period of Shinto-Buddhist syncretism, while keeping in mind the presence of Muromachi Bakufu appointed governors (kubo 公方) of Kamakura. The line of betto who managed the Shrine's Buddhist affairs during the period have been described in the sources as strictly disciplining the Shrine's monks, replacing those they accused of misconduct, in the process of continuously and freely exercising their powers of appointment and thus expanding their sphere of personal influence over the monks under their jurisdiction. On the other hand, we also see a rise in incidences of monks resisting the authority of their betto, to an extent that during the last years of the Muromachi Bakufu, betto were altogether prevented from replacing their subordinates. Concerning the case of Koken, who served as the Shrine's 20th betto between 1355 and 1410, issuing directives to his subordinate monks using the seal of the Kamakura Kubo in Oei 7 (1400), the research to date has interpreted this act as a surrender of betto authority to the governor ; however, a rereading of the related primary sources reveals that such a general conclusion can not be reached from one isolated incident. Although there is no record of Koken's successor Sonken replacing any of his monks, there is the incident in Oei 22 (1415) in which the prestigious mountain ascetic title of "In" was bestowed on the Shrine's monks, but excluded any one not belonging to the Shingon (Toji Temple) Faction of esoteric Buddhism, indicating a discriminatory attitude towards those monks not under the betto's personal influence. Then a struggle arose over the appointment of Sonken's successor, which reverberated into secular politics, leaving Son'un as betto by virtue of the mass replacement of the Shrine's monks. Son'un's term of office was marked by further worsening of relations between the Shrine's betto and his monks, which developed into a situation of such turbulence that the Kamakura Kubo showed signs of possible intervention in the Shrine's personnel affairs, and ended up replacing Son'un. Incidentally, Sonchu, the Kubo's replacement, was executed for collusion with Ashikaga Mochiuji in the Shogun's younger brother's "rebellion" of 1438-39. The process by which the Buddhist sector of Tsuruoka Hachiman Shrine was transformed from an non-sectarian center of learning to a predominately Shingon Faction dominated institution, beginning in the mid-14th century, was by no means a peaceful one, as indicated by the rise of serious tension during that time between the Shrine's betto and the monks under their jurisdiction.