Recent trends in the development of major Russian cities are raising questions about the end of post-socialist transformation. Post-transformative urban trends have become visible in the context of the planning and realization of iconic architectural projects. Their purpose is to symbolize a capacity for innovation and competitiveness. At the local level, however, they are subject to controversial debates, especially when challenging regional traditions of urban planning. The Okhta-Center, a business and cultural center with a skyscraper reaching a height of 400 m, serves as a good example. The Gazprom Group intended to build the complex at the edge of the historical city center of Saint Petersburg. During the height of the debate the project involved not only the citizens of Saint Petersburg, but also the leadership of the Russian Federation and UNESCO. Analyzing the discourse regarding the Okhta-Center therefore allows insights into current trends of urban development in Saint Petersburg as well as strategies of Russian domestic and foreign policies.