This paper situates Ptolemaeus Chennus’ treatment of Alexander the Great in the Kainē Historia within the miscellany tradition, and demonstrates how he engages directly in the discourse of his day concerning Alexander. The Alexander anecdotes furthermore reveal the parodic nature of the text: rather than to inform those seeking knowledge as the author claims in the preface, the Kainē Historia provides an opportunity for the already erudite reader to flaunt their own pre-existing knowledge that is necessary to unlock the jokes that sit at the heart of each anecdote. Consequently, the Alexander anecdotes should be understood as a means through which Ptolemy mocks not only the miscellany genre, but also the obstruse knowledge contained therein and the role it played in the performance of paideia.