This paper examines how legacies of thinking about ontology, logic, and how best to approach knowledge representation have become interwoven in the architecture of the technologies that enable a Semantic Web. As a cultural anthropologist, I approach this study with qualitative historical and ethnographic methodologies, positioning the community of researchers that have been involved in the design and implementation of Semantic Web protocols and technologies as my primary field site. Two concepts from Science and Technology Studies are introduced - thought styles and design logics. The paper demonstrates how diverse thinking about how to approach knowledge representation on the Web is rooted in debates that emerged in artificial intelligence in the 1970s and 1980s. It then goes on to discuss how the diverse approaches to Web semantics that emerged from these legacies have cultural and political implications. The paper concludes with a call for further research that positions Web architectures as objects of social and cultural study.