The overriding message in the play is the struggle for freedom, which manifests itself in several ways. The idea of racial freedom is addressed through the many references to slavery. During the play, Henry meets a slave, Williams, who plans to go "North as I kin git! They say the Norther ya git, the free-er ya git!" However, although Henry supports Williams's escape to Canada, he warns him that men in the north are not free, either: "Every man shackled to a ten-hour-a-day is a work-slave. Every man who has to worry about next month's rent is a money-slave."

This idea of being chained to institutions, even within a free society, is expressed further through Henry's individual struggle. When he is confronted by Sam Staples, the friendly constable tells Henry he has to pay his taxes to help support the war. Henry, however, refuses to pay on the grounds that he does not support the war and says that he does not want to be part of a society that does:

If one honest man in this state of Massachusetts had the conviction and the courage to withdraw from this unholy partnership and let himself be locked up in the County Jail, it'd be the start of more true freedom than we've seen since a few farmers had the guts to block the British by the bridge up the road.

With statements like this about various social institutions and with his resulting actions—Henry does have the courage to be locked up—Henry proves that he is willing to stand up against conformity, a phrase commonly referred to as "rocking the boat." This phrase is given a very literal translation in the play when Henry is in a boat with Ellen Sewell, whose father has forbidden her or her brother, Edmund, to attend Henry's school. Says Henry: "Stand up to your father! (He stands. The boat rocks.)" This action terrifies Ellen, as it does society.

Finally, the lack of freedom is expressed through dialogue, specifically the words "get along" and "go along," which are used by various characters to imply that one should just "go along" with whatever society dictates. When Henry wants to complain about the fact that his cellmate, Bailey, has been waiting three months for trial, Bailey stops him, saying he does not want to "make a ruckus. I'm not a troublemaker. I just want to earn my keep, make a little tobakky money, and get along." As Henry says to Bailey, "'Get along!' Those words turn my stomach." At the beginning of the second act, Lydian tells Henry that "in order to get along, you have to go along," a statement that enrages Henry, who responds by shouting "GO ALONG! GO ALONG! GO ALONG!" Shortly after that, Waldo tells Henry that "We have to go along with the majority!" a statement that again frustrates...

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