In 1954, he became counsel for Pan American World Airways in New York City; he remained at Pan Am until 1966. From 1967 to 1969 he was a Visiting Fellow on the Council on Foreign Relations in New York City, and testified as an expert witness before the Committee on Foreign Affairs of the House of Representatives in Washington. In 1970-1971, he was a Visiting Professor at Sarah Lawrence College and at Brooklyn College. He later worked for International Telephone and Telegraph, where he became General Counsel for ITT-Latin America.
Over 16 years, Crassweller reviewed some 700 books for Foreign Affairs, the magazine of the Council on Foreign Relations; he also reviewed for the New York Times book section. He wrote three books on Latin America: Trujillo: The Life and Times of a Caribbean Dictator (1966), The Caribbean Community: Changing Societies and U.S. Policy (1972) and Perón and the Enigmas of Argentina (1987).
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