This chapter deals with the ambiguity that political authorities feel toward culture and history when they are pressed to enlarge and modernize urban infrastructures. I will discuss the strategy followed by the Harbour Works Department of Macau as the city sought to reposition itself as an international trade centre. I examine Macau's spatial transformation between 1910, when a progressive regime came to power in Lisbon, and 1930, when the first extension phase of the Porto Exterior facilities was completed.