Teaching human rights means taking on a series of controversies over what human rights are, how they are determined, and how they are (or are not) upheld. The "possession paradox" is that often human rights are declared but many, or even most, people do not actually enjoy them. In teaching human rights we must convey both the promise of human rights and the discrepancy between that promise and their fulfillment. I review a number of controversies in the current application of human rights, many of which arise from that discrepancy. I then suggest the use of literary works and simulation games that can sometimes convey meanings more effectively than expository material.