In its current form, the integration of AI into journalism threatens the autonomy and quality of journalistic labor, media workers’ intellectual property rights, and the economic sustainability and editorial independence of news organizations. As AI becomes increasingly ingrained in news work and business, news outlets risk becoming reliant on commercial third-party infrastructure they do not control, further entrenching the power of “big tech.” These political economic concerns are at the heart of decisions about AI adoption in newsrooms and the future sustainability of journalism. This chapter derives some key lessons and critical concepts from previous technological and economic transformations of the news industry. In particular, the chapter outlines three broad technological shifts: (1) the digitization of news, (2) platformization associated with search engines and social network sites, and (3) the commercialization of AI. Critical concepts that have been used to theorize previous changes include digital labor, platformization, and infrastructure capture. These ideas provide a critical foundation for understanding the AI moment. By taking a historically informed, political economic approach to journalism and technology, this chapter avoids the mistakes of thinking AI is completely new or inevitable. This approach suggests that questions about how, why, and what AI technologies are integrated into journalism remain open to contestation.