Philodemus was the author of a history of philosophy entitled The Ordering of the Philosophers. Histories of the Academic and Stoic Philosophers are a part of this larger work. He was also the author of sharply polemical treatises against other philosophers, among which On the Stoics stands out for its hostile engagement and partisan sarcasm. Since Domenico Comparetti’s edition of Philodemus’ history of the Stoic philosophers, the contrast between his treatment of the Stoics in these two treatises has been well appreciated. What has not been appreciated is the explanation of this contrast. I argue that Philodemus’ twin treatises, Academicorum Historia and Stoicorum Historia, lack the polemical engagement and vigor of a work like On the Stoics because they reflect his interest in philosophical proselytizing and education so impressively displayed in his On Frank Criticism (Περí παρρησíας). This essay probes into the connections between this work and Philodemus’ histories—not of Academic and Stoic philosophy—but of the Academic and Stoic philosophers as educators and practitioners of the art of παρρησíα.