This research analyzes contemporary public art and proposes a new concept of site-specificity, focusing on public art theory, sociological space theory, and representative public artworks in the global city. After the emergence of Suzanne Lacy’s New Genre Public Art, the discourse and practice in the contemporary public art scene developed around site-specificity based on physical sites and communities. The social relationships, however, changed by digital mobility and social networks, and artistic capitalism has followed through mutual imitation of industry and art. There is a need to understand the site-specificity of public art as complex logic. I explain it by referring to Kwon Mi-won’s site-specific art theory and Henri Lefebvre’s spatial theory. Then I analyze the complex logic that connects cultural policy, artistic intention, and the community and site, focusing on Kapoor’s Cloud Gate as the representative public art of Chicago. It can be evaluated as having an open specificity of a site and a potentiality for producing an aesthetic space not tied to the physical site. However, it is also important to note that Kapoor’s sense of community and public contribution through his works are not high, and it is difficult to separate people’s reception of them from the circuit of artistic capitalism.