Theodore’s fifth cousin, Franklin Delano Roosevelt, was the first sitting president to travel by airplane during his time in office. He primarily used two airplanes for transportation: the Dixie Clipper and the Sacred Cow. During the 1930s, Pan American World Airways asked manufacturers to design an aircraft that would facilitate passenger travel and mail transport across the Atlantic Ocean. In 1936, the winning entry came from the Boeing Aircraft Company of Seattle, Washington. Pan Am contracted Boeing to build six 314 Clipper "flying boats" with an option for six more in the future. Twelve aircraft were eventually made, nine of which were operated by Pan Am, and the other three by British Overseas Airways Corporation. Measuring 106 feet in length with a wingspan of 152 feet, Boeing’s 314 Clipper was literally a colossus of the sky. It weighed nearly 41 tons, had a range of 3,500 miles, and held a cruising speed of 183 miles per hour. It also made intercontinental travel a comfortable experience. The aircraft was manned by a crew of 10, and could carry up to 70 passengers at a time. It featured a 14-person dining room, lounge, and group seating divided by compartments.3

The Dixie Clipper, one of the twelve Boeing 314 Clippers, made its first transatlantic flight on June 28, 1939. Over 5,000 spectators turned out to watch the plane take off from Manhasset Bay on Long Island. There were 22 passengers and 11 crew members on board. Their final destination was Marseille, France by way of “Horta, the Azores, and Lisbon, Portugal.” Tickets for the flight were priced at a staggering $375 for one-way travel or $675 round-trip, which would amount to $6,623 or $11,922 in today’s dollars. With stops along the way to France, flight and layover time was estimated to be around 48 hours.4 According to one newspaper, the passengers made reservations “years ago for this first flight.” There was, however, one booking unaccounted for—reservation number one—made by Will Rogers, the famed actor and cowboy personality. Rogers had died in an airplane crash in Alaska four years earlier with aviator Wiley Post.5 Nonetheless, the Dixie Clipper arrived safely in Marseille two days later, making its maiden European voyage a tremendous success.6

The aircraft was also used to transport American representatives and foreign dignitaries out of harm’s way as Nazi Germany advanced through Western Europe. William C. Bullitt, United States Ambassador to France, watched as the Germans defeated the French on their way to Paris in June 1940. Bullitt felt communications with American officials were now compromised. This prompted him to leave for the states in July to inform the president on the alarming situation in Paris. On his return flight aboard the Dixie Clipper he was joined by the former Empress of Austria and Queen of Hungary Zita, along with her daughter Princess Elizabeth, who had fled Belgium for Portugal. Zita’s sons, Archduke Otto and Prince Felix, were already in New York awaiting the arrival of their mother and sister.7

The plane also transported individuals who would prove vital to Roosevelt’s policies and communications. Republican candidate Wendell Willkie, the president’s opponent from the 1940 election, traveled to London in January 1941. Despite their differences, Willkie and the president agreed that the United States needed to support Great Britain and its allies against the Axis Powers. Roosevelt asked Willkie to meet with American and British officials, as well as hand-deliver a letter to British Prime Minister Winston Churchill. Upon his return, Willkie met with the president and First Lady Eleanor Roosevelt at the White House on February 11, 1941. While he was already a supporter of the Lend-Lease Program, the trip convinced Willkie to advocate for Roosevelt’s foreign policy to members of his party and the American people.8