ABSTRACT
This chapter compares the record of Singapore during the Second World War with each of Britain’s ‘fortress colonies’: Bermuda, Gibraltar and Malta. It contests Churchill’s rhetorical flourish that Singapore was ‘the Gibraltar of the East’. Unlike Singapore, an entrepôt from the outset, each ‘fortress colony’ had originally been annexed for the defence of the seaborne empire, a role which was resumed in 1940. In sharp contrast to the material defences of Gibraltar and Malta, together with the leadership of their military governors, the security of Singapore was hobbled by misplaced confidence in the island’s natural defences and disputes between service chiefs and civil authorities.
