The intention of Theophrastus’ Characters still escapes us. This paper offers a new answer to that centuries-old question by looking closely at the one political sketch of the collection: ‘The Oligarch’ (C.26). We argue that C.26 reveals a political intention in the Characters, presenting oligarchy as the inherently flawed projection of a character trait onto political events. Read in this way, C.26 appears as a medium through which Theophrastus can take a definite but careful stance in contemporary Athenian politics.

Plutarch's Moralia mentions that Theophrastus twice delivered his native city from tyrants (1097B, 1126F), a detail that has been difficult to make coherent with our existing understanding of Theophrastus’ life. Theophrastus seems to be in the wrong place at the wrong time for this to have been possible, or to have been too undemocratic and scholastic a philosopher to have wanted to participate in these struggles in the first place. By more closely examining the nature of Plutarch's comment and the evidence for Theophrastus’ political orientation and character, this article argues that there are, however, grounds on which to take Plutarch's report seriously. It presents a case for Theophrastus’ participation in two liberation struggles in 334 and 332, without complicating the trajectory of his accompanying Aristotle to both Macedonia and Athens during this period.