Yes, freedom is earned within ones self
No, there is no way a suppressed man can be a free man
Freedom is a trait, and its wholly possible for a suppressed man to have it.
Yes you can be free in a dictatorship to an extent, of course.
Possible doesn't mean always able to be free.
Freedom as an ideal is not easily stamped out. Measurable, personal freedoms can be held under a dictatorship if they are allowed by the law, or if the freedoms are enjoyed in secret. I suppose that it could be argued though, that the fact these freedoms are enjoyed in secret implies that the people involved in the violations are silently rebelling, planting the seeds of a possible revolution (potentially overthrowing the dictatorship). Regardless, it is possible to have some measure of personal freedom under the law of a dictator.
Let's look at this in a Realist's perspective. If you have a "good" dictator who gives special rights and privileges that is associated with freedom he still has abosulte power and authority. This power and authority is then passed down when the original dicator dies. He could have the same mindset as his father but more than likely he's been born with a silver spoon in his mouth as they say. He would be more snobby. If not he than his children or there's. Ultimately, you will get a self-entitled, evil dictator who inherits the right to rule you with absolute power. History shows us this happens. For example, when Julius Caeser took power in Rome he had good intentions. He made reforms and changes that benefited the people, but as time went on we got emperors like Nero who burned down a large section of downtown Rome. I don't even need to get into Nazi Germany that would be several pages long. What have we learned from this? With absolute power comes no freedom, but oppression.
You cannot be free, because the moment you are free you become a threat to the state.