Globalization theorists often claim that the rapid economic rise of the Asian Tigers is best explained by their adherence to free market principles. However, the economic growths of Singapore, Taiwan, and South Korea are usually attributed to their state managed economic development policies. Of the four, Hong Kong's path to success was the only one that was a result of a liberalized economy with little government intervention. Since their economies share the most similar colonial and geographical characteristics, Hong Kong (the apparent outlier) was compared with Singapore to ascertain whether there are two paths to success within the four Asian Tigers. This study found that their economic ideologies, their governmental development strategies, and their geo-political factors have helped to create and explain the different developmental paths to success of Singapore and Hong Kong over the past 4 decades.