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When Winston Churchill urged his fellow countrymen to take a stronger stand against Nazism, he faced opposition not only within the government but also in the media, both in the UK and in the United States. This paper will examine Churchill’s relationship with two of his most powerful political opponents (and personal friends) in the British media—the Nazi sympathizer Lord Rothermere of the Daily Mail and the pro-appeasement Lord Beaverbrook of the Daily Express. It will also explore how Lord Beaverbrook proved to be an especially wily adversary for Churchill because he encouraged U.S. newspaper publishers to fight for isolationism and appeasement in their country. Churchill had to transcend this hostile transatlantic media environment as he sought to persuade the British and American public of the dangers of Nazism.