Abstract: A law professors’ global conversation on ‘progressive property’ confirms institutions of private ownership as foundational for individual human freedom and dignity, while also insisting on the design of such institutions with a view, grounded in the principle of the equal value of every person, to the ability of each person to access and enjoy these values of the institution of property. The conversation takes as a premise that a design for a good and just system of property entitlements is not deducible from any single metric but rather falls unavoidably to political judgment and choice. That does not mean, though, impulsive choice, but rather choice through the exercise of deliberative reason and critical judgment leavened by tradition and experience. This article seeks illumination of the progressive-property paradigm through a consideration of three judgments from Associate Justice Johan Froneman, in cases before the Constitutional Court of South Africa on property under that country’s constitution. The discussion takes its turn towards what it names as a pragmatist strain in our received traditions of political argument – finding in the judicial work of Froneman J, as represented in these judgments, characteristics of realism, contextualism, a mediation of functional and formal demands on adjudication under a rule of law, and an optimistic outlook on the possibility of political practical reason.