This thesis focuses on the Huaihai Campaign (Nov. 6 1948 - Jan.10 1949) in the Chinese Civil War (1927-1936, 1949-1950). This war involved the Republic of China’s (ROC) Kuomintang Party (KMT) and the emerging Communist Party of China (CPC). Over the course of a few months and around one million combatants, the Communists pulled off a resounding victory dealing the final blow to the KMT which led to the CPC’s governance over mainland China. This case study of two key turning points in the Huaihai Campaign is analyzed using Sun Tzu’s five net assessments from The Art of War. Although the KMT appeared the much superior force on paper, they were dealt a decisive blow during the Huaihai Campaign. This thesis uses Sun Tzu’s five net assessments to explain the root cause of KMT decision failings. The KMT failures stemmed from ignorance of the most basic and vital military axioms of assessing advantages and disadvantages before going into battle.