In his letters to Lucius Papirius Paetus from 46 bc Cicero provides striking reports on his thoughts and activities as he seeks to accommodate himself to the new political realities following Caesar's decisive victory over the republican forces in Africa. In these letters Cicero also engages in a kind of performative role-playing: he casts himself variously as a teacher of oratory to two of Caesar's close associates (Hirtius and Dolabella), as a bon vivant immersed in the Caesarian social scene, and as a man of moral principle who measures himself against the model of the wise man. Philosophical jokes, allusions, and arguments all figure prominently: Cicero is evidently drawing on a rich range of philosophical material to frame his actions and how he should be judged. This paper brings out the full significance of these underlying philosophical frameworks and makes clear the ways in which Cicero exploits the resources of the Greek philosophical tradition in his self-fashioning in the letters to Paetus.