[...]
Freedom is slavery. I gave a shiur on the definition of cherus around Pesach time. The gist of it was that the less choice you have, the more free you feel. [...]
I think that might be better expressed as "Slavery is freedom" (or "Only a
slave to the truth is free," as Rabbi Akiva Tatz quotes from the Chazon Ish.)
However, if we suggest that experienced freedom is in inverse proportion to one's freedom of choice,
it follows that actual slaves and prisoners should feel the most free, which I'm confident they don't.