At first glance the estoppel argument for rights and punishment is compelling however there are a few issues I have with it. For the moment I will only present the most damaging one as I see it: that the circumstances of action are not taken into account.
In Punishment and Proportionality, Stephen Kinsella presents the following argument:
Suppose that A murders B, and B’s agent C convicts and imprisons A. Now, if A objects to his punishment, he is claiming that C ought not treat him this way. Otherwise, he fails to object. The ought is a “strict” one, since A claims that C must not punish him. By such normative talk, A claims he has a right to not be punished. In order to “object” to his punishment, A at the least must necessarily claim that the use of force is wrong (so that C should therefore not punish A). However, this claim is blatantly inconsistent with what must be his other position: because he murdered B, which is clearly an act of aggression, his actions have indicated that he (also) holds the view that “aggression is not wrong.”
The problem is that Kinsella’s argument hinges on the idea that the murder demonstrates the norm that murders in general (that is, all murders) are proper. However, the murder does not show that A holds the view that murder is not wrong but that the particular murder was not wrong. The only way to show that A holds the view that all murder is permissable is if he explicitly argues it (or somehow murders people in every conceivable circumstance).
Let’s say A asserts that the murder was justified on a particular form of consequentialism. He is asserting that “the initiation of force is permissable when the ends justify the means”. If the murder is justified by the ethical theory and his punishment is not justified by the same theory, he cannot be estopped from his claim. If the punishment is justified by the same theory then he can be estopped from his claim that the punishment is not proper. If the murder is not justified then either A must make a different claim or accept the punishment. Note that this argument applies to all forms of universalizable ethical theory not just this naive utilitarianism. This basically means that estoppel only works when a person is hoist by their own petard.
However, most people are not Socrates and are not willing to drink the hemlock so easily. In order estop A’s opposition to punishment it is necessary to prove that the punishment is in accordance to A’s ethical theory. If A objects to C’s interpretation of the facts or their understanding of the theory, the discussion completely avoids estoppel and turns into an argument about ethics. In the same way, if C cannot prove that the punishment is justified then A cannot be estopped and the discussion must turn to ethics.
At the moment it seems to me that estoppel does not establish a system of rights and a theory of punishment. I am curious to know if this criticism has been brought up before.