Aenesidemus, the (re-)founder of Pyrrhonian skepticism, is usually said to have begun his career by breaking away from the Academy. This assertion rests on the word “συναιρεσιώτῃ” as it appears in Photius’ summary of Aenesidemus’ Pyrrhonian Discourses. I argue that Photius’ probable understanding of the Academy’s history undermines this traditional reading. I then examine the evidence external to Photius and conclude that it also speaks against the traditional narrative.