In this article, the relationship between Miklail Markovitch Borodin and Chiang Kai-shek is discussed in three aspects. One is their cooperation in military affairs. Another is their power struggle in Kuomintang. The other is their breakup which happened during the same time when Kuomintang divided into left- and right- wing factions. The cooperation and breakup of Borodin and Chiang are closely related to their control over the military. In the early phase of their connection, they tended to cooperate with each other. Later, their conflicts broke out as their individual power increased and solidified. Borodin used his power in Kuomintang to restrict the growing of Chiang's military power, while Chiang used his exploits in Northern Expedition to gain the right to speak in politics. In the end, with the success of Northern Expedition, Chiang also outdid Borodin and set up his legitimism in Kuomintang. The clash between Borodin and Chiang in politics was eventually settled by war, with the real strength playing the most decisive factor. This accounts for the struggle between Borodin and Chiang, and this also applies to the struggle between Chinese Communist Party and Kuomintang.