Was the Cold War inevitable, and who is responsible for its outbreak? This chapter argues that, as the Second World War neared its end, Joseph Stalin was shopping for a great bargain with the Allies, in keeping with Russia's realpolitik tradition. While the details of Stalin's vision remain blurry, evidence from internal Soviet deliberations in 1944–45 points to a broadly imperial, nineteenth-century, conceptualization of the Soviet role in Europe. Stalin sought both power and legitimacy, and understood that the Americans could endorse or reject his postwar claims. He could and did measure his appetites in pursuit of legitimate gains—those that had Washington’s imprimatur. Despite his efforts to achieve legitimacy at Yalta, Stalin’s hopes for a Soviet–American agreement to divide the world soon began to run aground, largely owing to his own rapacity and bad faith.