T. J. Madison: Rad Geek, most tyrants seem to do rather badly.
This is certainly true. In fact, I think it’s analytically true that all tyrants do badly, because one of the things that tyrants have to do in their lives is be tyrannical, and living your life by lording it over other people and living off of their honest labor is a pathetic and rotten way to be.
If you mean that tyrants also suffer from psychological or material evils (like anxiety, frustration, loneliness, discontent, material deprivation, etc.) then that is certainly also true more often than a lot of people realize. But given that a life of cannibalism, bullying, and phoney posturing at martial glory is pathetic even if it is pursued in absolute contentment and full of the most exquisite pleasures, that sort of appeal to the external punishments that a life of monstrous vice may, empirically, end up inflicting on you, seems to me to be wholly beside the point.
Stefan: Then on what basis can we condemn Agathocles for slaughtering old men for his personal gain if he was happy with the results, secure in his position, and had successfully repelled Carthage and governed Sicily peacefully for many years before dieing in old age?
The basis on which we can condemn him is pretty obvious: he’s a murderer and a tyrant. (If condemnation, as a social practice, was not made for murderers and tyrants, who was it made for?) You might think, though, that having condemned him, there is still an open question about whether or not we can convict him of being irrational, or give him reasons not to do what he did. I think that you can; they are roughly the reasons that I sketched out in replying to T.J. above. (If you could be absolutely sure that you could get away with murdering a rival and taking all his possessions, would you do so? If not, why not?)