If a society valued freedom as highly as possible, sending someone to prison would be such a spectacular condemnation that great accomodations would be offered. Instead, prisons serve as a demeaning punishment and eternal condemnation.
There is great moral value in taking the liberty stance: it would mean that prison would not be a great punishment for the great number of innocent and wrongfully incarcerated. And It would also be a lot easier to prosecute all kinds of crimes, as prison would not be as terrible as it is (but, if freedom valued, still a punishment)