Harold E . Thompson Harold E . " Tommy " Thompson ( 1921 - October 29 , 2003 ) of Hobart , Indiana , was a helicopter aviation pioneer . He was the first man to intentionally loop a helicopter , set three international helicopter speed records , and was the first man to land a helicopter in the courtyard of The Pentagon . Thompson was a veteran of 3 , 500 hours in single - engine propeller fixed - wing aircraft and 3000 more in helicopters . Life . Having spent two years at Purdue University , Thompson was called up into the United States Army Air Corps in 1943 , a week after he had married his childhood sweetheart , Carolyn Kramer . Thompson served as a P - 47 instructor at Moore Field in Mission , Texas until January 1945 , when he earned an assignment to the Army ' s first helicopter class at Chanute Field , Illinois . Later , he was assigned to the Bridgeport , Connecticut , plant of Igor Sikorsky , who pioneered helicopters in America . After the war , " Tommy " as he was known , got a job as one of Sikorsky ' s three test pilots — in the trial and error days . The plant produced six helicopters a month , mostly hand built . Engineers tinkered with new designs , and the test pilots tried them out . Most of the early models had slow , sluggish controls - some flew as expected , but others didn ' t . Thompson was also Igor Sikorsky ' s personal pilot . By 1949 , Thompson was an experienced helicopter pilot . He had been through some forced landings and crashes , but had not been seriously injured . Records set in the S - 52 . In 1949 , Sikorsky engineers developed the Sikorsky S - 52 helicopter . " It was a sharp , responsive dream , " Thompson recalls . " After trying some mild acrobatics , I figured it would loop . " Until Thompson , no one had dared try to loop a helicopter . As Sikorsky ' s chief test pilot Jimmy Viner pointed out , " Any of 10 things can go wrong - - all fatal , be sure you know what you ' re doing . " Thompson did — erratically at first , then perfectly — 10 loops in all , as a movie camera recorded the flight for history . That year , he went to the Cleveland air races with the S - 52 , where he set the first of three international speed records that he was to achieve in the helicopters : over . Flight instructor . Thompson also taught others how to fly helicopters . His students included Admiral Arthur W . Radford ; Pat Handy , first woman to fly solo in a helicopter ; and Rodman Wanamaker , Eastern department store tycoon . Last flight . His career came to an abrupt halt on a spring day in 1950 , when he took an admiral aloft at the Navy ' s Lakehurst , New Jersey , base . Suddenly , a shaft snapped , and the tail rotor came apart . Thompson skillfully kept the craft from spinning around , the usual result of such an accident . The helicopter landed hard , crushed the landing gear and tilted , while the spinning overhead rotor chewed up the ground and disintegrated . Tommy crawled out with nothing worse than a cut cheek . The admiral was shaken , but game : " All in a day ' s work , eh , boy ? " Thompson however had walked away from more than 20 forced landings and now his fifth helicopter crash . Figuring he had stretched the law of averages too far , he replied , " Maybe for you , sir , but not for me " . That night , when he got home he talked to his wife and refrained from flying again in a helicopter until 1979 . Later life . After his flying career came to a halt , he moved back to Hobart , Indiana , and began working with his father , delivering fuel oil for the Standard Oil Company . In 1979 , Thompson visited the Tucson Convention Center where a large helicopter convention was taking place . He immediately was recognized for his feats during the convention and given the opportunity to pilot one of Sikorsky ' s S - 58s . Currently he is honored at the Smithsonian National Air and Space Museum in Washington , D . C . outside the entrance to the Steven F . Udvar - Hazy Center . Thompson can be found on Panel # 37 , Tablet # 1 , Column # 1 . Thompson died on October 29 , 2003 in Hobart , Indiana . He was survived by his wife Carolyn .