He was trained as a journalist at the University of the South, in Sewanee, Tennessee, and began his career as a reporter at the Chattanooga News. He joined after the New York Herald Tribune, where he was sent as a correspondent to Geneva (Switzerland) from 1931 to 1935, to report on the League of Nations. He had a brother named Spires Whitaker who worked as a doctor for the army during World World War World War II
In early 1936, he covered the Second Italo-Abyssinian War for Columbia Broadcasting System, accompanying the Italian troops.
He also interviewed Mohamed Mizzian, a Moorish general working with the Fascists, and reported on Mizzian giving two captured teenage girls, one found with a trade-union card, to some forty of his troops for mass rape.
Whitaker described how Mizzian "smirked when I remonstrated with him. "Oh, they"ll not live more than four hours," he said".
He moved back to Europe in mid-1939, in connection with World World War II, working for the Chicago Daily News and the New York Post. As a convinced democrat, his articles criticized the atrocities of the regimes of Mussolini and Hitler.
They made the fascist regime uncomfortable, and in 1941 he was ordered to leave Italy.
At the time of his expulsion from Mussolini"s Italy, Time reported that Whitaker"s dispatches were "displeasing" to the government.