In Tusculans 1 Cicero gives a lengthy rebuttal of the thesis that death is an evil. This raises a puzzle: how can such a one-sided presentation aspire to reveal whether it is more plausible that death is or is not an evil? Invoking the Tusculans’ practical aim – the removal of emotional disturbance – does not fully satisfy, since it is unclear how effective persuasion can be if the contrary position does not receive a fair hearing. I show that as main speaker in the book Cicero warns against over-confidence in embracing positions that one wishes to be true; and I argue that as author Cicero portrays the interlocutor of Tusculans 1 as a salutary example of how not to approach the kind of questions about death with which the work engages. We are encouraged to see the interlocutor’s failure as one not of character but of inexperience in philosophical method.