In “The Night Thoreau Spent in Jail,” Bailey is a fellow prisoner who shares the jail cell – and the main scene -- with Henry Thoreau. The action of the play returns to the two men often. Bailey says he was put in jail for burning down a barn, and he claims that he didn’t do it. He is waiting for his trial. He is an uneducated man. Henry teaches him how to spell and write his name. They were not friends and had not known each other before meeting here. They talk about a variety of subjects. Bailey is thus a new audience for Henry, and we are able to learn more about Henry through what he discusses with his cellmate. This may be the purpose of the character of Bailey: to be a sounding board for the main character.

This play is a piece of historical fiction, based loosely upon the facts of Thoreau’s life and especially on the incident of his spending one night in jail in July 1846 for not paying the Massachusetts poll tax. Thoreau himself wrote about this development in paragraphs 25-32 of his essay “Civil Disobedience,” and offered a shorter version in the third paragraph of “The Village” chapter of his book, Walden.  In the 27th paragraph of “Civil Disobedience,” Thoreau explained that he did have a roommate in the jail cell, and the man had been accused of burning down a barn. Therefore, the character of Bailey was based on an actual but unidentified man who shared the county jail cell with Thoreau in real life.