Can we live in a free society without personal privacy? The question is worth pondering, not only in light of the ongoing debate about government surveillance of private communications, but also because new technologies continue to erode the boundaries of our personal space. This Article examines our loss of freedom in a variety of disparate contexts, all connected by the thread of erosion of personal privacy. In the scenarios explored here, privacy reducing activities vary from government surveillance, personal stalking conducted by individuals, and profiling by data-driven corporations, to political actors manipulating social media platforms. In each case, new technologies and open platforms are used by a bad actor to harm unwitting indiv...