The relations between the People’s Republic of China and the Republic of China have steadily improved since Ma Ying-jeou has won the presidential elections in 2008. Hitherto research focuses rather on systemic or structural respectively on political assertions to explain the improved cross-Strait relations. No research has been done so far that focused on the personality of either Chen Shui-bian or Ma Ying-jeou and how their personality influenced the cross-Strait relations. This paper attempts to close this academic gap and to explain to which extent the improvements can be attributed to a distinguished view of the world between Ma Ying-jeou and his predecessor Chen Shui-bian. For this reason, an operational code analysis based on public statements (interviews and speeches) was employed to assess the particular worldview of Chen Shui-bian and Ma Ying-jeou. The results suggest that Ma Ying-jeou’s operational code contributed to the improved current situation across the Strait.