The present work collects all of the historical-biographical prose of the important twelfth century poet and polygraph Theodore Prodromus, active as a teacher and a lettré during the reign of the Comnene emperors John II and Manuel I. This critical edition of the collected letters – the first of its kind – appears together with ten elaborate speeches (four of these are monodies or funerary speeches), originating in the same learned milieu and stylistically close to the letters. Both sections of this volume display the refinements of twelfth century Byzantine literary art and rhetoric, revealing at the same time the originality of a highly self-conscious writer who, if deliberately indebted to a great Hellenic past, succeeds in preserving his own colourful self by his eloquence, his eccentric wit and the sheer pleasure he finds in literature and language, in reading and writing.