This chapter explores the structural difficulties faced by progressive reforms aimed at redistributing rural property through constitutional provisions. In different historical periods, legal scholars and activists have placed their faith in constitutional reforms and adjudication to attack rural property concentration in Latin America. The objective of this chapter is to analyze some of the limitations that constitutional law and judicial interpretation have had in Colombia. It argues that redistribution is stalled by the coexistence of different definitions of property; the concentration of public resources for economic development plans that privilege a liberal classical view of growth, property and distribution; existing conflicts between access to land, the right to work and the right to develop enterprises, as well as the contradictions between identities at the margins who may be provided with collective titles to property. In order to delineate the presence of these same contradictions in other contexts, the chapter ends with a short parallel to the Bolivian case.