The transformation of former industrial areas is important to urban redevelopment, although such activity is often limited by possible on-site pollution, complicated ownership, and legal constraints. Rather than treating these areas as a problem, many cities recognize the advantages of redeveloping them because of their often central locations. Some are transformed through a temporary city event with the participation and support of external organizations and planned as a part of the urban development. This paper is an in-depth case study on the planning perspectives of Expo 2010, Shanghai, China, a regeneration project on a former industrial site. By scrutinizing the case with the details based on compiling information, contextualizing the project, and comparing the expectation and reality during the preevent, event phase, and postevent phase of the project, it is found that (1) governmental participation plays a key role in the transformation of former industrial area with city event, especially on the site where it has not completely finished its industrial activities; (2) the main motivation and significance of regenerating the former industrial area is to boost city redevelopment in the long term; and (3) a successful transformation is determined by not only the first stage from preevent to event phase but also the second stage from event to postevent phase. All these features provide a deep insight into the redevelopment of a former industrial area.