This study develops a port-to-port comparative political risk assessment and conducts a case study of the political environment evaluations of five East Asian ports: Hong Kong, Singapore, Busan, Kaohsiung and Shanghai. This system approach consists of political risk factor identification, risk measurement and assessment processes using the three methods of Delphi, analytic hierarchy process and Ward's clustering. Fifteen high-ranking managers from five leading global carriers present their viewpoints for analysis. The empirical case concluded that political risk was a strong indictor for the business environments of the host ports. Jointly, the micro-risks resulting from the port development and management policies were considered to be more significant than the macrorisks from the integrated political and economics conditions. Political risks of the five host ports were assessed as ranging from 0.17 to 0.38, so these ports were considered to be politically secure for the global carrier business. Finally, the five ports were statistically clustered into three groups to signify the differences in their political environments.