What should we do with a tyrant?
A timeless question, for at least the past two and a half millennia

It’s hard to be in beautiful Syracuse, Sicily, as am I right now, and not think of tyrants. As I explained in a previous post, discussing Plato’s adventures in the city, it seems that for a long while Syracuse was bent on exchanging one tyrant for another. But the prompt for the current essay was actually composed several centuries later, in March 49 BCE, to be precise.
Marcus Tullius Cicero was writing to his lifelong friend Atticus because he was trying to make up his mind whether to support Julius Caesar—whom he perceived to be a potential tyrant—or Gnaeus Pompey, who was nominally defending the Republic, but in fact had a good chance of himself becoming a tyrant, if given the opportunity. Here is what struck me forcefully in what Cicero writes:
[In order] not to surrender myself wholly to sorrowful reflexions, I have selected certain theses, so to speak, which have at once a general bearing on a citizen’s duty, and a particular relation to the present crisis: Ought one to remain in one’s country when under a tyrant? If one’s country is under a tyrant ought one to labour at all hazards for the abolition of the tyranny, even at the risk of the total destruction of the city? Or ought we to be on our guard against the man attempting the abolition, lest he should rise too high himself? Ought one to assist one’s country when under a tyrant by seizing opportunities and by argument rather than by war? Is it acting like a good citizen to quit one’s country when under a tyrant for any other land, and there to remain quiet, or ought one to face any and every danger for liberty’s sake? … Even if one does not approve an abolition of a tyranny by war, ought one still to enroll oneself in the ranks of the loyalists? Ought one in politics to share the dangers of one’s benefactors and friends, even though one does not think their general policy to be wise? … By keeping myself at work on questions such as these, and discussing both sides both in Greek and Latin, I at once distract my mind for a time from its anxieties, and at the same time attempt the solution of a problem now very much to the point. (Letter IX.4)
There is so much going on here, and it is so pertinent to similar situations throughout history, including in recent times, that I’d like to unpack it carefully.
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