I begin here by discussing the role of Leibniz in historical thought, particularly in Frank Ankersmit’s representationalist philosophy of historiography. I then discuss Jouni-Matti Kuukkanen’s recent criticism of Ankersmit’s commitment to holism about the semantics of historiography. I argue that the criticism fails because Kuukkanen is not sufficiently sensitive to the Leibnizian foundation of Ankersmit’s holism. Ankersmit can absorb Kuukkanen’s criticisms into his Leibnizism. I conclude by suggesting that the philosophy of historiography needs to be connected to substantial projects in the philosophical criticism of historiography.