Roosevelt and Churchill forged a close friendship as their countries struggled against Hitler, but their relationship did not begin well. They had first met in 1918 at a dinner in London, when Churchill was minister of munitions and Roosevelt the young assistant secretary of the navy. Churchill quickly forgot the encounter, but Roosevelt did not. Years later he recalled that Churchill acted like a stinker and was one of the few men in public life who was rude to me. As president, Roosevelt put his feelings aside in 1939, when Churchill returned to the post of first lord of the admiralty. It is because you and I occupied similar positions in the First World War that I want you to know how glad I am that you are back in the Admiralty, he wrote. After Churchill became prime minister in 1940, he and Roosevelt met a second time for a wartime conference aboard ship off the Newfoundland coast in August 1941. And Churchill traveled to Washington several times after the United States entered the war, even spending the Christmas holidays at the White House after the attack on Pearl Harbor.

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Following the start of Operation Torch, Roosevelt planned to meet with Churchill in Casablanca early in 1943. It would not be an easy trip for the 60-year-old president, and his aides worried that he might not be up to it. Polio had confined Roosevelt to a wheelchair since 1921, making an already strenuous round-trip journey of nearly 17,000 miles even more of a challenge. But the president was determined to make the journey, and a thorough physical examination put presidential physician Admiral Ross T. McIntire's worries to rest.

Roosevelt loved an adventure, and he loved to travel — even if his travels, at least as president, had been confined to leisurely train trips and jaunts by car. Roosevelt had not flown since 1932, when he traveled from Albany, New York, to Chicago to accept his nomination at the Democratic national convention. In fact, no U.S. president had ever flown while in office. The Secret Service still regarded flying as a dangerous mode of transport. For the trip to Casablanca, however, air travel was the only realistic option, as German submarines lurking in the Atlantic made a surface crossing too risky. Early in the morning of January 11, Roosevelt's train reached Miami. Waiting there were two flying boats, Boeing 314s chartered by the navy from Pan American for wartime duty. The four-engine 314s were the largest commercial aircraft of their day. They could carry 40 overnight passengers in relative luxury and had a range of 3,500 miles. One of them, the Dixie Clipper, had inaugurated the first regularly scheduled service across the Atlantic in June 1939. This was the airplane designated for the president and his personal staff, including Admiral McIntire, Admiral William D. Leahy, the president's chief of staff, and Harry Hopkins, the former social worker turned presidential aide and advisor. The pilot, navy reserve Lieutenant Howard Cone, held the title Master of Ocean Flying, the highest commercial pilot rating. Other members of the party boarded the second flying boat, the Atlantic Clipper. Once everyone was aboard, the two flying boats taxied out to begin the long journey to Trinidad, the first stop.

Lieutenant Cone had a happy passenger that day. Hopkins wrote that the president was so thrilled to be making the trip that he acted like a sixteen year old. Over Haiti Roosevelt asked Cone to detour over the Citadel, a fortress FDR had visited in 1917 when he was assistant navy secretary. But Admiral McIntire worried as the unpressurized plane reached its cruising altitude of 9,000 feet, and he saw the president occasionally turn pale in the thin air.

Admiral Leahy had contracted the flu, and he remained behind in Trinidad. Roosevelt wrote to Margaret Suckley, his cousin and confidante, I shall miss him, as he is such an old friend and a wise counselor. Leahy would have been especially valuable as an advisor on the knotty problems of French politics. By 1940 Germany had occupied most of France but had allowed a French regime based at Vichy nominal independence over the remainder, and Leahy had served as Roosevelt's ambassador to the Vichy government. Issues relating to France were especially convoluted in North Africa. Algeria and Morocco were French colonies, and the Americans coming ashore for Operation Torch had initially fought against defending Vichy troops.

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