A popular definition of freedom is “the ability to do what you want”. If you accept the claim that tyrants or dictators are among those most able to do what they want (since the rest of humanity is always to a larger extent bound by laws and the actions of others), then it follows that a tyrant is the archetype of a free person.
Except if you believe – as I do – that freedom is not only – or even primarily – the ability to do what you choose, but also the availability of significant choices. And a choice is significant when you have the ability to expand the options you can choose from and the ability to make an educated choice between expanded and examined options.
Now, how do you widen the available choices, and check if what you at first think you want is really what you want after reflection and consideration of all the available options? Only if all possible options and choices are flooded with the light of publicity. When you see which options are available, when you hear people freely discussing in public the merits of different options and objects of volition, only then can you make an educated choice.
This publicity requires a legal system and legally protected human rights. These rights open up the options, allow other options to appear and show the merits of all options. These rights improve your volition and hence give something more than the mere ability to do what you want. They allow you to take a step back and reflect on what it is that you want.
Only in a public space protected by legal rights, where everybody is equal and where everybody can speak and listen in an equal way, can we examine our options. So we see that freedom needs equality in the sense of the equal participation in public life. If there’s no equal participation, then some possible options and some arguments for or against some options will not appear, and, as a consequence, a free choice isn’t possible.
Now if we return to the case of the tyrant, we can say that he’s not more free than his subjects. A tyrant does not have access to a public space because a public space needs the protection of human rights, something which a tyrant gets out of the way as soon as he can.
The point of Herodotus’s equation of freedom with no-rule was that the ruler himself was not free; by assuming the rule over others, he had deprived himself of those peers in whose company he could have been free. In other words, he had destroyed the political space itself, with the result that there was no freedom extant any longer, either for himself or for those over whom he ruled. Hannah Arendt