This chapter, discusses megaprojects in Istanbul, Sydney, and Hong Kong. We offer a panoramic view of the various controversies, difficulties, obstacles, negative impacts, and civic opposition associated with constructing these megaprojects. We show that the nature and shaping of the projects owes to the socioeconomic, developmental, institutional, and geographic contexts in which they emerge. However, we also see that these urban megaprojects—regardless of context—constitute disorderly and contentious enterprises and have intrinsic potential (often realized) to elicit substantial controversy and criticism that fundamentally questions the parameters of the projects as envisioned and publicly presented by their promoters. The megaprojects are disorderly enterprises, in that they substantially modify the physical appearance of cities and their urban fabric, often triggering socioeconomic imbalances and realignments in urban power arrangements in growth machines and civil society. Megaprojects are contentious enterprises because of the complex composition of stakeholders with conflicting interests in their planning, construction, management, and governance. This complexity often results in major obstacles to megaproject implementation, strategic misrepresentation of costs and benefits, optimism bias about megaproject impacts among planners and promoters, and a widespread perception among urbanites that these structures are negative for their cities.