Joseph Schumpeter's term "creative destruction" can be employed to examine Joyce's representation of the rise of the modern city in Finnegans Wake. The Wake re-enacts the story of how the modern city, with its straight streets and busy thoroughfares, opened up the closed world of the medieval city, with its crooked streets and organic tangle of lanes and alleys. This paper examines Joyce's use of 11th Edition of the Encyclopedia Britannica in his depiction of the division of the city into poles of poverty and privilege in the modernizations of Belfast, London, and Budapest. Baron Haussmann's plan for the regularization of Paris is also contrasted with Camillo Sitte's championing of the medieval values in his opposition to the geometrization of Vienna. Finally, Marshall Berman is employed to demonstrate Joyce's ambivalent relation to modernism—both deploring its destructions of the past while celebrating its dynamic novelty in creating the future.