In 1921, Tomlinson earned his wings as a naval aviator and in the late 1920s was a member of the Three Seahawks, an aerobatic team that preceded the Blue Angels. He later resigned his regular Navy commission and went into commercial aviation. While working for Transcontinental and Western Air, he was involved with Douglas Aircraft in the testing of the DC-1, DC-2, and DC-3 cargo-passenger planes. The company later became Trans World Airlines.
He and his wife flew via TWA to the 1987 Annapolis visit. At lunch after the interview, Mrs. Tomlinson pulled from her purse some complimentary miniature bottles of vodka she had received during the flight. They added a kick to the Bloody Marys.