 Although Philo’s philosophy of education is identified most closely with mitigated skepticism, its origin may also be tied to Clitomachean radical skepticism. Scholarship on Cicero, our best source for the defense of argument on either side on educational grounds, has increasingly defended radically skeptical interpretations of some of his dialogues (Brittain 2016: Cappello 2019; Wynne 2018 &amp; 2021), and Cicero himself associates it with Arcesilaus and Carneades (see On Divination 2.150, Tusculan Disputations 5.11 &amp; 5.83). It may seem that radical skeptics would not have justified argument on either side for educational reasons because they argue for purely destructive ends. But one may think that radical skepticism can ground a Socratic interest in others’ training in dialectic out of a hypothetical acceptance of rational norms (see Brittain 2005 [2008]). If this is right, then Philo in the Roman Books had further cause for identifying its critical method as the defining mark of the Academy.