As Artificial Intelligence continues to permeate everyday life, concerns over its societal consequences are becoming increasingly pressing. Anticipatory practices have emerged as central to responsible AI development, offering ways to envision and mitigate potential harms. While policymakers engage with anticipation through forecasting and risk assessment, speculative design offers an alternative, more experiential approach to also fosters public engagement and critical reflection. However, most speculative explorations focus on future possibilities, often neglecting the continuum between these and past phenomena. In this pictorial, we argue for integrating historical perspectives into speculative design to enrich anticipatory work on AI. Through a week-long international summer school, we engaged with the legacy of phrenology and the work of Cesare Lombroso. Using this as a springboard for speculation, we illustrate that incorporating historical trajectories into speculative design can deepen understanding of current dilemmas around AI, but dedicated methodological resources are still needed to achieve this value.