The “America First” approach to foreign policy represents an opportunity to reassess relations with Russia. Efforts to deter Russian aggression have failed. Perhaps a new approach is needed. This article uses the lessons of the Peloponnesian War to help guide the West’s approach to Russia. By examining the three motivations for warfare—fear, honor and interest—it is possible to craft a more effective deterrent strategy while avoiding a security dilemma. Current approaches have discounted legitimate Russian fears of NATO and EU encroachment. They also have neglected the role of honor in Russia’s actions and how this impulse frames Moscow’s views of the West. Finally, NATO and the EU have lost sight of Russia’s vital interests in pursuing further eastward expansion. Where the West cannot compromise is on the security of NATO and EU members and the unity of the Trans-Atlantic alliance.