"Man, born free, is everywhere in chains" (Jean-Jacques Rousseau's Social Contract)"Freedom is nothing else than a chance to be better" (Albert Camus)"Freedom, freedom, prison of the free" (Lawrence Durrell)"Freedom (n.): To ask nothing; To expect nothing; To depend on nothing" (Ayn Rand)"Freedom's just another word for nothing left to lose" (Kris Kristofferson, 'Me and Bobby McGee')
But what does Avot have to say on the subject? In the view of our Sages the highest form of freedom is that which is obtained by dedicating oneself to the study of Torah. As Rabbi Yehoshua ben Levi teaches (Avot 6:2), "You can have no freer person than one who engages in Torah study".
This statement is on its face difficult to comprehend. How can a person be free if he spends his entire time sitting in front of books that contain the canon of Jewish learning? Apart from anything else, he has no time that is "free" to do other things like going to the beach or cinema. It would seem then that this teaching is not addressing issues like free time or freedom of mobility: rather, it addresses freedom to serve God and fulfill His requirements in the most free and unfettered manner. In this sense a person can be incarcerated in prison yet still be free, if only he has some means of learning Torah and carrying out such mitzvot as are available to him. Incidentally, elsewhere in Avot we see a teaching that reinforces this message, that a person can never complete his service of God, yet nor is he "free" to desist from it (2:21).
Conveniently, Hebrew has two words that are translated into English as "freedom" -- but they carry quite different connotations. The word used in Avot to connote freedom to serve God is cherut, while the word employed to describe the setting free of slaves and prisoners is shichrur. Effectively, shichrur is an emancipation, a "freedom from", while cherut is a "freedom to". The two concepts should never be confused with one another.