This chapter details Thomas Jefferson’s dealings with Ezra Stiles, President of Yale and New England’s leading intellectual. Stiles became Jefferson’s confidant in 1786. Meeting only a month before Jefferson embarked overseas from Boston on July 5, 1784, the two men enjoyed an immediate connection, despite their divergent roles and regions. A master of many disciplines, Stiles was most distinguished by a single interest in particular: his facility with Middle Eastern languages. Jefferson shared anxieties with Stiles concerning Muslim captivity—captivity not of a single person, however, but of an entire nation, sharply criticizing Ottoman occupation of Greece. Anticipating future experiences of his new friend and a later U.S. President, Stiles also gained access to manuscripts arising from Muslim captivity and Arabic documents written by African slaves.