Chapter 1 recovers the history of an Iberian family involved in royal service across Portugal and Spain during the first decades of the Iberian Union (1580–1640). It shows how family memory and political loyalty became professional assets for young, university-trained jurists. By moving back and forth between courtly and university stages across the two monarchies, some of these young letrados came to think of themselves as political polymaths. Ultimately, they found opportunities to reach out and receive support from transnational networks of neo-stoic thinkers and practitioners which was fundamental for articulating the composite social and political life of the Iberian monarchies within and beyond the Iberian Peninsula.