Henry VI, Holy Roman Emperor

Henry VI, son of Frederick Barbarossa, became King of Germany at four and Holy Roman Emperor in 1191. Educated in Latin and law, he was also a skilled poet, though that refinement didn't soften his methods. His 1186 marriage to Constance of Sicily brought inheritance claims he spent years enforcing: an epidemic broke his 1191 siege of Naples and his wife was captured, but an enormous ransom extracted from Richard I of England bankrolled a second attempt. He took Sicily in 1194, then ruled it with such ruthless suppression he earned the epithet "il crudele." He threatened Byzantium into paying the Alamanikon tribute, made Cyprus and Cilicia subjects, and tried twice to make the empire hereditary - the prince-electors refused. He pledged a crusade in 1195, crushed a Sicilian revolt in 1197, and watched his fleet depart that September. He died of malaria in Messina days later, and the throne dispute that followed tore the empire apart for nearly two decades.