Hugh Clifford has been described as “one of the most unusual colonial governors in British history”. Widely regarded as the “doyen of the colonial service”, Clifford held successive governorships in the Gold Coast, Nigeria, Ceylon, and the Straits Settlements. As a writer of novels, short stories, and reminiscences, moreover, he enjoyed a successful literary career; he moved in literary circles and counted Joseph Conrad among his particular friends. Clifford's inspiration was drawn almost exclusively from his experiences in Malaya, the territory where he not only started his career in the early 1880s, but also ended it in tragic circumstances nearly fifty years later. Throughout his Malayan career Clifford came into frequent contact with Malaya's ruling families. “To act the part of officer in attendance upon Malayan royalties is a task with which circumstances have familiarised me”, he declared in “Piloting Princes”, a 1902 contribution to Blackwood's Magazine. His attitude towards them ranged from disgust and condemnation, to admiration and a paternalistic concern for their dignity and survival. Unravelling Clifford's complex, and apparently contradictory, relationship with Malay royalty will be the subject of this article.