Abstract Since the founding of Singapore, two conflicting ideologies concerning this port city emerged. On one hand, the British East India Company insisted that Singapore should serve primarily as a transit port for its trade with China, with minimal government investment. They established transit infrastructures such as lighthouses and docks, not only to facilitate trade between India and China but also to generate revenue by trade taxes for the company. On the other hand, the Straits merchants based in Singapore, who conducted their business in Southeast Asia, advocated a free port policy. They vehemently opposed any form of taxation and government interference. In their resistance to the Raj's taxation on the transit infrastructures in Singapore, the Straits merchants positioned themselves as proponents of liberal and enlightened economic policies while also constructing an identity for the Raj as despotic, corrupt, and oriental in nature. This cultural construction against the Raj provided the Straits merchants with the legitimacy to advocate for Singapore's separation from British India in the 1860s.