The Army procured a dedicated presidential aircraft, the transport version of the Consolidated B-24D Liberator four-engined heavy bomber known as a C-87A, and named Guess Where II. The plane carried first lady Eleanor Roosevelt – but never her husband.
On Jan. 11, 1943, Roosevelt took off from Dinner Key Seaplane Base in Miami as a passenger in a Boeing 314 Clipper named the Dixie Clipper.
Over the objections of many in the Secret Service and in the executive mansion, Roosevelt mustered his great sense of historical drama and used it to fly from Miami, Fla., to Casablanca, Morocco, in January 1943. At that juncture, Guess Where II was not yet available. In fact, although plans were forming for a military squadron to transport the president by air, Roosevelt found himself journeying aboard a civilian plane.
The president was traveling for a meeting with British Prime Minister Winston Churchill and other Allied leaders. The Secret Service ruled out travel by sea, leery of the threat from German submarines. On Jan. 11, 1943, Roosevelt took off from Dinner Key Seaplane Base in Miami as a passenger in a Boeing 314 Clipper named the Dixie Clipper.
Roosevelt had taken the presidential rail car, the Ferdinand Magellan, from Washington, D.C., to Miami. There, he boarded the Clipper, a long-range, four-engine flying boat used for transatlantic flights before World War II. For the president’s comfort, a double bed was installed. Lt. Howard M. Cone of the Navy Reserve was the pilot during this first presidential flight.
Roosevelt’s flying trip was enough to test anyone’s stamina. With eight other passengers accompanying the president, pilot Cone embarked on a journey consisting of three segments, beginning with a 1,633-mile flight to Port of Spain, Trinidad. The next day, the silvery, triple-tailed Clipper continued on a 1,227-mile leg for Belen, Brazil, covering the distance in about eight hours. Roosevelt and the other travelers rested overnight again. The following day, the Clipper piloted by Cone flew the longest leg of this expedition, covering the 2,500 miles (4025 km) to Bathurst, British Gambia, in West Africa.
The second pilot to provide transportation to Roosevelt was Otis Bryan, a major in the Army Reserve and a vice president of Trans-World Airlines. Bryan was waiting in Bathurst with a Douglas C-54 Skymaster being operated by TWA under a contract to the government. Thus, although a C-54 was being readied in the United States as Roosevelt’s personal aircraft, a different C-54 carried him onward, taking Roosevelt 1,500 miles to Casablanca.
Roosevelt spent a fortnight in North Africa. He returned to Washington by retracing his path aboard the same two aircraft.
Roosevelt subsequently traveled to conferences in Tehran and Cairo aboard another TWA C-54 Skymaster, rather than the C-87A Liberator Express that had been built for his use.
On June 12, 1944, pilot Maj. Henry T. “Hank” Myers traveled to the Douglas Aircraft plant in Santa Monica, Calif., to pick up a new C-54 and deliver it to Washington National Airport, where it would be assigned to the 503rd Army Air Base Unit of the Air Transport Command. The unit was a precursor to today’s 89th Airlift Wing.