Tyranny was the worst fate not so much because it deprived one of liberty as because it deprived one of virtue. The corrupting effects of living in tyranny—the dehumanizing sycophancy and the degrading collaboration necessary to avoid the tyrant’s bad graces—were more abhorrent and disgusting than the oppression itself.
This is an important distinction that is not apparent to many modern US libertarians, especially among conservative Republicans. Perhaps the American Founders understood it better because of their classical education. It is also a fundamental problem in any social grouping, and even in theology as distinct from religion. The problem is not with the injustice of tyranny; the problem is with the distortion of character in those who learn to live with tyranny, or may even prefer it.