In his fascinating book, Churchill and Orwell: The Fight for Freedom (Penguin Press, 2017), Thomas E. Ricks explains the intriguing and, at times awkward, relationship between Churchill and Roosevelt that ebbed and flowed privately and publicly, to the point that Churchill eventually chose not to attend FDR's funeral. Ultimately, however, they allied to defeat Adolf Hitler, though Ricks suggests Churchill's deep affection was always really for the nation FDR led, not the man himself.
As early as 1939, Churchill and Roosevelt had begun communicating directly about the war, bypassing Joseph Kennedy who, at the time, was U.S. ambassador to London. Roosevelt apparently had no qualms about going around the ambassador, though this was a rather unprecedented move, because he believed Kennedy—the father of John F. Kennedy—was too willing to negotiate with the fascists.
Kennedy’s methods were suspect too—at one point, he told Roosevelt that in order to fight totalitarianism, the U.S. would have to adopt “totalitarian methods." Ricks reports how the diaries of Roosevelt’s aides show the extent to which the president didn’t trust Kennedy. Roosevelt told one associate he thought Kennedy was “disloyal to his country.”
In the fall of 1940, FDR finally got rid of Kennedy. When interviewed by reporters, Kennedy told them “Democracy is finished in England” and possibly in the United States, so there was no sense for America to bother joining the war. FDR and Churchill didn’t share this defeatist mindset; they believed the Axis powers could be defeated, and so they continued to correspond as much as ever.
FDR could only aid Churchill so much, though, as long as the U.S. was not officially in the war. The first two years of the war dragged by slowly and the ultimate outcome of the war was still very much in the air.
Then came December 7, 1941—the day the Japanese empire attacked Pearl Harbor in Hawaii, killing more than 2,000 Americans, and a day that, in the words of President Franklin Roosevelt, “will live in infamy.” Churchill felt a tinge of glee at the news. He knew that Pearl Harbor meant that America, who had for years remained “neutral” on the sidelines, would finally be joining the war effort
When the U.S. declared war on Japan that December day in 1941, Churchill could hardly mask his sense of relief. Describing his response to later memoirs, Churchill said the U.S. declaration of war meant that:
“England would live. Britain would live; the Commonwealth of Nations and the Empire would live… We should not be wiped out. Our history would not come to an end. We might not even have to die as individuals. Hitler’s fate was sealed. Mussolini’s fate was sealed. As for the Japanese, they would be ground to powder. All the rest was merely the proper application of overwhelming force.”
Some of Churchill’s advisors thought his unbounded optimism was unrealistic, but for the prime minister, the U.S. entry into the war meant the war was, for all practical purposes, over. When the U.S. declared war on Japan, Japan’s ally Germany in turn declared war on the U.S., and so America would focus on the European front first.
Shortly afterwards, Churchill spent two weeks at the White House, getting to know FDR. Even during this first trip, Churchill’s and FDR’s differing priorities became apparent. Churchill spoke to Congress of the necessity of maintaining, not only England, but the British Empire as well. Americans for their part didn’t give a hoot about the British Empire and were hardly bothered by its post-war dissolution.
FDR’s and Churchill’s working relationship would cool as the war effort continued, and this was largely brought about due to disagreements over how to best handle Joseph Stalin. FDR thought he was better equipped to handle Stalin, and Churchill thought FDR was naïve to the kind of man Stalin really was. The very fact that the U.S.S.R. was counted among the “Allies” in World War II and, when the war was over, sat in judgment over the Nazis at the Nuremberg trials is one of the great ironies of history. The U.S.S.R’s presence among the Allies illustrates the morally ambiguous natures even of wars that are being fought for just causes. As far as murderous dictators of the 20th century are concerned, Stalin was arguably worse than Hitler, and having to relate to him as a “colleague” during the war was at times a stretch for both FDR and Churchill.
Churchill, FDR, and Stalin met personally for the first time at the Tehran Conference in the fall of 1943. Churchill left the conference in what Ricks calls a “dark mood”. During a dinner meeting, Stalin spoke casually of executing tens of thousands of German generals once the war was over. Disgusted, Churchill stormed away from the table. That week FDR began meeting with Stalin in private, while refusing to hold private meetings with Churchill. Tehran was “the first time Roosevelt began to act as if he held the senior role in the partnership.” Churchill began to see that post-war England would only be a shadow of its former self, likening Russia to a giant bear, America to an elephant, and describing England as a mere donkey in comparison.
As the war progressed, the most decisive battles of the end of the war would be led by American, not British, troops. Military campaigns that Churchill advised against, U.S. troops proceeded with anyway, sometimes successfully, making people question Churchill’s judgment. Churchill saw that when the war was over, it would be America that would emerge as the world’s new economic and military powerhouse.
Churchill’s less than friendly feelings about FDR became most evident in April 1945 when Churchill opted not to even attend FDR’s funeral, saying “government business” prevented him from such a trip. Ricks questions Churchill’s sincerity because “despite his claim of urgent government business, he went off for a country weekend and danced a Viennese waltz with his daughter.” People close to Churchill said that he and FDR had never exactly been “friends”—the war effort was all they had ever had in common. Others said they did have a friendship of sorts, albeit an unusual one.
Whatever awkwardness existed between Churchill and FDR, Churchill was throughout his life far more “pro-American” than many of his British colleagues in government. Churchill was the son of a British father and an American mother and so some critics said his “loyalties were divided." At his funeral, which he designed, he had American flags flying alongside British ones. He even requested that Battle Hymn of the Republic be played. U.S. president Lyndon Johnson declined to attend or even send his vice president, “perhaps remembering Churchill’s slight of FDR’s funeral twenty years earlier”, Ricks said.