This chapter analyses Sri Lankan politics through the entanglement of kinship, caste, and masculinity, arguing that political authority is not only won electorally but also inherited, cultivated, and performed through family networks and elite institutions. Moving from the late nineteenth century to the present, it traces how “political families” (from the Senanayakes and Bandaranaikes to the Rajapaksas) turned lineage into legitimacy, and how dynastic continuity has persisted despite democratic procedures and periodic promises of rupture. The chapter foregrounds elite colonial schools such as Royal College and S. Thomas’ as key sites where a ruling-class masculinity was produced—through discipline, sport, Christian-coded respectability, and later its translation into Sinhala-Buddhist nationalist idioms. It then reads political biographies and family narratives as gendered scripts that naturalise leadership as patriarchal inheritance, even when women enter power through familial roles (widowhood, wifehood, dynastic succession). The final sections show how these logics continue in contemporary politics—from Ranil Wickremesinghe’s “meritocratic” image sustained by elite alliances to Mahinda Rajapaksa’s quasi-sacral elevation—demonstrating that the personal remains profoundly political in Sri Lanka.