Hugh Clifford has been described as “one of the mostunusual colonial governors in British history”.Widely regarded as the “doyen of the colonialservice”, Clifford held successive governorships inthe Gold Coast, Nigeria, Ceylon, and the StraitsSettlements. As a writer of novels, short stories,and reminiscences, moreover, he enjoyed a successfulliterary career; he moved in literary circles andcounted Joseph Conrad among his particular friends.Clifford's inspiration was drawn almost exclusivelyfrom his experiences in Malaya, the territory wherehe not only started his career in the early 1880s,but also ended it in tragic circumstances nearlyfifty years later. Throughout his Malayan careerClifford came into frequent contact with Malaya'sruling families. “To act the part of officer inattendance upon Malayan royalties is a task withwhich circumstances have familiarised me”, hedeclared in “Piloting Princes”, a 1902 contributionto Blackwood's Magazine. Hisattitude towards them ranged from disgust andcondemnation, to admiration and a paternalisticconcern for their dignity and survival. UnravellingClifford's complex, and apparently contradictory,relationship with Malay royalty will be the subjectof this article.