Let's imagine a scenario. A man, thinking about his life, decides that it is time for him to choose a guiding principle, a highest good, upon which he will from that point onward base his decisions. He ends up choosing freedom as that principle. He reckons that freedom is what we all value and seek, fundamentally - when we acquire money we acquire monetary freedom, when we acquire skills we acquire freedom to act, etc etc. Makes sense, right?
He decides to quit his job, sell all his belongings and realize true freedom as the ability to live anywhere in the world, do anything he wishes and so on. He gets to an airport with what little rudimentary is left of his belongings and decides to pick a city.
Now we get to the problem. What should he pick, so as not to lose his freedom of choice? What can he pick? He can get on a plane, but once he's there, he can no longer get on another plane: he is committed, and has therefore lost his freedom. Not to speak of the money: he will lose it, and therefore his monetary freedom to travel!
This is relevant in so many cases of human anguish. The scrooge endlessly saving up money but unable to use it; the man who hoards up a bookshelf of books but cannot commit to reading a single one; the western millenial, with so many options open, yet unable to live anything out, existing in a kind of vestibule of life, unable to get out of bed with 'no purpose'.
I think it is a contradiction to place freedom as a value. Freedom is simply a passing phase, a corridor we enter into briefly to move from one state into another. It is highly valuable to those who are in a bad state (thus, slaves seek freedom), but it is no universal value in itself, unless we wish to fall into a paradox like this one.