In 1959, he was hired by "The Washington Post". Wolfe has said that part of the reason he was hired by the "Post" was his lack of interest in politics. The Post's city editor was "amazed that Wolfe preferred cityside to Capitol Hill, the beat every reporter wanted." He won an award from The Newspaper Guild for foreign reporting in Cuba in 1961 and also won the Guild's award for humor. While there, Wolfe experimented with fiction-writing techniques in feature stories.