For the criollo elite, the optimism regarding Puerto Rican progress outweighed any sense of heritage loss in the aftermath of the 1898 Spanish–American war. US authorities promised that a colonial moratorium on civilization and democracy would be raised. The old walled city, a symbol of claustrophobia and colonial despotism for some intellectuals, should be transformed into a metropolis. Spanish centenary fortifications and buildings should be torn down, places renovated, and the city grid expanded and embellished. Scorn for the old city, however, came to a halt along frustration. The endurance of colonial rule transformed San Juan into an uncanny landscape in which opposite European city ideas clashed with US urban pragmatism, the immediate with the transcendent, utopia with waste. This chapter addresses the spatial outcome of political transition between empires dominance and the twist in meanings of the old walled city, once reviled, later signified as national heritage.