William Vanderkloot William J . Vanderkloot , Jr . ( 2 Jan 1915 Lake Bluff , Lake , Illinois - 8 Apr 2000 - Ocala , Marion , Florida , age 85 ) was a pilot who flew Winston Churchill over enemy territory on diplomatic missions during World War II . Early Years . Vanderkloot was the son of William J Vanderkloot and Florence M Cary . He was descended from Stephen Genung , of Morris County , New Jersey , who served as a private in New Jersey state troops during the American Revolution . William attended Culver Military Academy in Indiana , and though he commanded the academy ' s Black Horse Troop , a cavalry unit , at age 16 , he had long watched planes coming and going from the Glenview Naval Air Station . During summers , he worked as a ground crewman for a local flying circus so he could be closer to the airplanes . At his parents ' urging , he briefly studied law at the University of Virginia . But while he was there , Vanderkloot sold his car , bought a homemade aircraft with the money and , after a few flying lessons , crashed it . He later attended Parks Air College in East St . Louis , and during the 1930s was a pilot for Trans World Airlines . World War II . Vanderkloot went to Montreal in 1941 , before the Japanese bombing of Pearl Harbor , and volunteered with the Royal Air Force Ferry Command to transfer long - range planes to Great Britain . Arriving in Britain , he was ordered to RAF headquarters in July 1942 and asked by Sir Charles Portal , RAF chief of staff , if there was a safe , direct route from England to Cairo by air . In the specially modified B24 Liberator bomber " Commando " , which he had just delivered to Prestwick , Vanderkloot said he could make the trip with one stop in Gibraltar . He would at first head eastwards , staying over the sea in the afternoon , and then after dusk , turn sharply south , flying over Spanish and Vichy territory in Africa in the dark before turning east again for the Nile and approaching Cairo from the south . Thus the danger from land - based enemy aircraft in North Africa and Sicily would be avoided without having to fly halfway around Africa . Portal told Vanderkloot to " stay handy to the telephone " . The next day Vanderkloot was taken to Winston Churchill ' s residence at No . 10 Downing Street . Churchill , clad in robe and slippers , offered him a drink , beginning a relationship that had Vanderkloot flying the Prime Minister on sensitive diplomatic trips across war - torn Europe , Russia , North Africa and the Middle East . " He took calculated risks , " said his son , William III . " There was a lot more risk in flying back then . It was a frontier , and I think all the old pilots will say it , secretly to themselves , that they enjoyed being on their own . It was the wild blue yonder . " As Churchill ' s pilot , Vanderkloot conveyed the Prime Minister to Egypt to sack Claude Auchinleck , commander of the British army in North Africa and took Churchill to high - level talks in Moscow with Joseph Stalin , to Turkey to determine that country ' s wartime intentions , and to the Casablanca Conference in 1943 . Post War . Vanderkloot headed the aviation department of Johns Manville Corp . in New York , piloting executive jets and helicopters . He retired in 1970 to Florida .