This chapter will offer a fresh interpretation of the importance of Dionysius’ rhetorical essays and in particular of the importance of his essay on Lysias for his critical work more generally. It will also revisit the question of the development in Dionysius’ rhetorical essays and argue that instead of seeing the essays progressing from one orator to another as an advancement of the critical competences of the author, it appears much more appropriate to view the progress from the perspective of a potential student. Dionysius emerges, then, as a writer and a teacher who is much more sensitive to the interests and abilities of his students than perhaps granted thus far.

Dionysius of Halicarnassus was a close reader of Plato and his engagement with the Phaedrus occupies an important position in his rhetorical essays and in his treatment of Lysias and Isocrates in particular. Between Plato and Dionysius, however, were three centuries of thinking and writing about rhetoric, compiling and commenting on the works of Attic orators, speechwriters, philosophers. Hence, before looking at Dionysius of Halicarnassus’ rhetorical essays, a brief overview of the reception of Lysias and Isocrates in the centuries between Plato and Dionysius is in order, so as to gain a good insight into the background for Dionysius’ work and to better assess his contributions to ancient rhetorical theory. The following overview will proceed roughly along chronological lines, focusing primarily on more substantial evidence on Lysias and Isocrates that we have from Ps. Demetrius, Philodemus and Cicero.