The British Empire provided the context in which both Winston Churchill and Franklin Roosevelt came to maturity and defined and aggravated their differences as national leaders. The chapter begins by comparing the shared beliefs and values of Churchill and Theodore Roosevelt on empire and race before showing how Franklin Roosevelt emerged from his cousin’s shadow to develop a hostility towards the British Empire inspired by genuine idealism as well as calculating pragmatism. It documents the tension between Churchill’s imperialism and his appreciation that American participation in the war was the key to victory, examining the differences between the two leaders before looking at their wartime relationship through the lens of their very different responses to events in the British Empire, especially in India. Churchill’s dispute with Roosevelt on the subject of the British Empire went to the heart of the relationship between a Democrat president who wanted to create a new world order imbued with American values and a Conservative prime minister who aimed to maintain the old world in all its glory. This disjunction threatened the stability of the wartime alliance.