This article explores three questions relating to the history of Singapore and the Straits with a focus on the period 1520 to 1650. The British colonial narrative posits that nothing of significance happened on the island for a period between the destruction of Singapore in the late 14th century until the founding of the British trading post in 1819. Drawing on materials of European origin, this article aims to unlock the perceived geostrategic value of the island before 1800 and investigates plans devised by the early colonial powers at the turn of 16th and 17th centuries to construct fortifications on and around the island, and found a colonial settlement. The article further investigates the cycles of destruction and reconstruction of the Singapore settlement in the 16th and 17th centuries.