Most people do not hold those who intentionally flout property laws in particularly high regard. The overridingly negative view of the property lawbreaker as a wrong-doer comports with the nearly sacrosanct status of property rights within our characteristically individualist, capitalist, political culture. This dim view of property lawbreakers is also shared to a large degree by property theorists, many of whom regard property rights as a fixed constellation of allocative entitlements that collectively produce stability and order through ownership. In this Article, we seek to rehabilitate, at least to a degree, the maligned character of the intentional property lawbreaker, and to show how property outlaws have played an important role in the evolution, modification, and transfer of property entitlements. We develop a typology of the property outlaw by introducing three particular kinds of property lawbreakers - the acquisitive outlaw, the expressive outlaw, and the intersectional outlaw. Descriptively, we show that each type of property outlaw has enabled the reevaluation of, and, at times, productive shifts in the distribution or content of property entitlements. What emerges from this study of the property outlaw is an alternative vision of property law that focuses, not only on its capacity for fostering order and stability, but also on its dynamic function as a site for the resolution of conflict between owners and non-owners. We argue that, if property is to perform this dynamic function, the law should be careful not to over-deter those who conscientiously and nonviolently refuse to abide by existing property arrangements.