The article traces the see-sawing fortunes of the Galatian ruler Deiotarus, how he gained and lost and regained control over various territories (the three Galatian tetrarchies; Lesser Armenia; and an unnamed coastal strip of land between Galatia and Lesser Armenia) from 63 BC until his death in ca. 40 BC. It also examines Cicero’s rhetorical strategy in his speech in Deiotarus’ defence before Caesar and argues that much in the speech cannot be taken at face value – many remarks of Cicero’s about Deiotarus are two-edged and should not be used uncritically in reconstructing Deiotarus’ career.