Three's company: The close working relationship between Franklin D. Roosevelt and Winston Churchill is one of the best documented between a U.S. president and a foreign leader. It was a friendship molded by the pressures of war: They spent 113 days together and exchanged more than 2,000 messages over the course of World War II, meeting nine times between 1941 and FDR's death in 1945. Despite the stakes, they struck up a distinctly informal friendship: After their first meeting in August 1941, Roosevelt told Churchill, "It is fun to be in the same decade with you." Churchill would later write, "I felt I was in contact with a very great man who was also a warm-hearted friend and the foremost champion of the high causes which we served."
Less well known is FDR's persistence in establishing a warm relationship with Stalin, or "Uncle Joe," as FDR and Churchill called him. In fact, FDR was far more suspicious of Britain's colonial habits and saw Stalin as a more suitable partner for global peace: "I think if I give [Stalin] everything I possibly can, and ask nothing from him in return, noblesse oblige, he won't try to annex anything and will work with me for a world of peace and democracy."