ABSTRACT :: The tax-free treatment of like-kind exchanges presents one of tax law’s most compelling equity conundrums. Tax law generally does not tax property holders on the property’s appreciation but does tax gain or loss recognized by property sellers and exchangers of non-like-kind property. In the basic Aristotelian system, equity requires that likes be treated alike, but the system does not provide criteria to determine what is alike. Depending upon the criteria, exchangers of like-kind property can be similar either to holders or to sellers and exchangers of non-like- kind property. The equity conundrum asks whether tax law should treat exchangers of like-kind property either the same as holders of property or the same as sellers and exchangers of non-like-kind property. This Article frames the conundrum in Rawlsian and Hohfeldian concepts. This framing suggests first that holders should not be taxed on property’s appreciation. Second, this framing explains that once tax law exempts holders’ appreciation from taxation, equity requires that exchanges of like-kind property should also be exempt from taxation. Thus, equity suggests that the tax law should treat exchangers of like-kind property and property holders similarly.