This chapter analyzes private criminal settlements through the lens of blackmail law. Private criminal settlements meet the definition of blackmail in every state, but there are reasons to think that they should be made legal. First, the theoretical justification for the crime of blackmail is relatively weak, and it is even weaker in the case of private criminal settlements. The chapter concludes by arguing that there are only two dangers that may arise from allowing private criminal settlements: first, that the blackmailer will become an accomplice after the fact and, second, that the blackmailer may be violating a moral or statutory duty to report the crime. However, these dangers could be alleviated by (1) increasing the punishments (and thus the deterrence level) for actively concealing criminal activity and (2) criminalizing any attempt to blackmail using incriminating information if the blackmailer has a statutory duty to report the crime in question.