In Edgar Allan Poe’s short story "The Man of the Crowd," the convalescing protagonist becomes entranced by the spectacle of a crowd, seeing in it a reflection of his own complex identity. This narrative invites us to consider the dual nature of crowds and the implications of this duality in relation to recent developments in Artificial Intelligence (AI) and Machine Learning (ML), and what effect these technologies may have on the space of the crowd. As facial recognition technologies proliferate, they transform what has historically been an experience of anonymity and potential, along with transformative healing when within a crowd, fundamentally altering our relationship to it.