This chapter presents Barangaroo within the literature on global megaprojects and provides an analysis of the course of events of this megaproject from the original design competition onwards. It examines the ambitions, progression and reception of Barangaroo. After conducting the largest global survey on megaprojects to date, B. Flyvbjerg was left with no doubt of the “Machiavellian formula for project approval, even if it means misleading parliaments, the public and the media about the costs and benefits of projects.” The chapter deals with an attempt to unpack the challenges behind the controversies of Barangaroo and thus frame bigger questions about the role of such a megaproject and the processes that produce the outcome. In the late 1980s, a few hundred metres south of Barangaroo, the 54-hectare Darling Harbour entertainment, cultural and commercial megaproject was developed on post-industrial waterfront land.