The Republic of China (ROC), also known as Taiwan, has been the haven of the Kuomintang (KMT) since its defeat at the hands of the Chinese Communist Party (CCP) in 1949. Taiwan has long been the subject of control by foreign powers, which has created a unique history for the autonomous region. Historical circumstances have created a space for a distinct Taiwanese culture that has diverged from that of the mainland. This paper examines the role of this newfound culture on civic engagement, specifically regarding the sentiment for separatism or lessened ties with the People’s Republic of China (PRC). I examine the history of the island by first discussing the evolution of Taiwanese culture over the 20th and 21st centuries. I take a closer look following Taiwan’s democratization, which developed a deeper cultural cleavage that is politically salient. Cultural cleavages have only increased the nationalist sentiment of the Taiwanese people in pushing for greater separation – if not full-fledged independence – from the PRC. The results of my historical analysis argue the relevance of culture theory on the growing divide between Taiwan and China. In addition, this paper provides a perspective the effects of identity politics in Taiwan and its effect on cross-strait relations.