The chapter examines the different phases of the wartime ‘special relationship’ between the UK and the USA. Roosevelt’s initial contact with Churchill was born of the realisation that American security was tied to that of the UK but with the over-riding caveat that the USA would not become ‘a tail on the British kite’. Initially, Churchill worked hard to convince Roosevelt that Britain was serious about continuing the war, while FDR pursued a strategy of hemispheric defence. Co-operation then increased with Roosevelt developing a policy of all aid short of war. Pearl Harbor ushered in the high-water mark of the alliance, albeit with disagreements about strategy. FDR saw an opportunity to draw the English-speaking peoples together to create a new, multilateral world order that rejected imperialism, while Churchill saw the war as a means to restore the British Empire and perpetuate British power. Roosevelt’s pursuit of a bilateral relationship with Stalin led to a final phase of increasing tension. Ultimately, the special relationship that emerged from the war would become far more important in the UK than in the USA, yet it owed much to the two people’s shared belief in preserving democracy.