The characters in Gem of the Ocean are all living in freedom, but are they truly free? How do you define freedom? Is it as much a state of mind as anything? Consider the characters one by one, and discuss how free you think each is. How does each person deal with his or her freedom? How does each character's freedom change throughout the play?

The central question of freedom is contrasted to enslavement in August Wilson's play. The author presents the idea of one character who embodies all enslaved persons: Aunt Ester Tyler. The paradox that Wilson offers is that—because she was enslaved for so long—once Emancipation arrives, Aunt Ester cannot be truly free. She is at liberty to live her life according to her own decisions, but she cannot completely escape the burden of suffering she bears from those centuries of bondage. A further paradox is contained in her calling as a "soul cleanser." for she has the gift of lifting the burdens that others bear.
Solly Two Kings and Eli seem to be the characters who most embody freedom. This is because they devoted their lives to helping others achieve freedom through their work on the Underground Railroad. Their resistance to the unjust system that was slavery showed that in their minds they could not be enslaved.
Caesar Wilkes, in contrast, seems to remain in bondage. He serves the figurative masters of legality and materialism. The relationship between law and justice escapes him. Because he is often incapable of making his own ethical decisions, he cannot be considered free.