De senectute, one of Cicero’s last works, has often been overlooked as an earnest but misguided tract on old age. This book re-examines it in the context of its composition in 44 BC, revealing a self-conscious, playful, and politically charged dialogue. It traces Cicero’s witty re-imagining of his protagonist, Cato the Elder, then explores troubling faultlines in the advice Cato gives. Cato’s exhortations to make use of the political authority of old age make little sense in a dictatorship, while his reflections on the horror of suicide cannot help but bring to mind his own great-grandson. In De Senectute, Cato the Elder seems to take aim at Julius Caesar.