What are some paradoxes in The Night Thoreau Spent in Jail?

The paradoxes that are used in the drama are done so to accentuate Henry's own activist stance enabling him to be seen as the most moral and spiritual of people in a world of conformity.  For example, Thoreau is seen as the ultimate activist, one who seeks to bridge the gap between Transcendental theory and the reality that is far from Transcendentalism.  In this, Thoreau is contrasted with Emerson, who is more intellectual and cannot move past the theory even when action is sorely justified by it.  The paradox here is that both men embrace the same philosophy which enables one to move and soar to action and causes another one to be impotent in taking a stand.  Another paradox would be seen in how the two brothers Thoreau approach being individualistic and following their own dreams.  When the school fails, John goes back to his conformist job "in the pencil factory" while Henry becomes even more staunch in his pursuits, without relenting.  The paradox here is that two believers in the same philosophical set of ideals and even in the same familial relationship can wind up on so different of paths.  It is paradoxical to see such similarity yield different results.  In both of these settings, the paradox or foil has been used to accentuate Henry's own position and his own status as being the idealistic man in a world devoid of ideals.

In "The Night Thoreau Spent in Jail", when does Henry's character seem paradoxical?

I would actually suggest that in his interactions with Bailey, there exists some moments of paradox in Henry's character.  The idea of breaking free from society's chains and standing up for what is right can be seen in Bailey's request for Henry to be his lawyer.  Henry has a moment where he can "act locally."  Yet, he refuses to do so.  Henry also teaches Bailey to write his name and then demands that he "unlearn it."  I think that this is a paradox because Henry, whose insistence on individuals following their own voice becomes intrinsic to his character, is demanding that Bailey do what Henry says.  In the end, it seems like Bailey is the perfect moment for Henry to focus on the embodiment of his philosophy.  Yet, there are instances in which Henry seems to be attracted to a bigger and larger cause, as opposed to truly understanding that the cause can exist on the smallest of levels, namely with his own vagrant of a cellmate.  I sense that in his interactions with Bailey, some moments of Thoreau's own paradoxical character is evident.