How does land privatization affect inter-generational economic welfare? European colonial administrations often implemented land settlement programs that privileged the allocation of private property rights to the detriment of indigenous communal tenure systems. I examine how colonial reforms of property rights and land titling affected post-colonial economic opportunity in the case of Jordan, a British colony from 1921 to 1946. I argue that socioeconomic status of new title holders conditions the economic impact of land settlement on individuals in the long-term. In order to test this argument, I leverage variation in the pre-reform proportion of villages' communal tenure to examine individual-level economic well-being after the colonial-era reform. Using quantitative case study of one of the first public schools in Ajlun and the 2016 wave of the Jordan Labor Market Panel Survey (JLMPS), I match individuals' locality of birth to their historical village and examine the effect of a village's historical musha' tenure on individuals' wealth, asset ownership, internal migration, and educational attainment. I find that the effects of land privatization varied across time. In the short term, children from peasant families were increasingly able to attend school due to the capital infusion from land titling. In the decades that followed, however, I find that the inter-generational effects of land settlement were negative for the rural poor. In general, positive economic effects of land settlement accrued to those with higher socioeconomic status, i.e., the children of fathers who completed higher levels of education or who were not primarily employed in agriculture. This paper contributes to our understanding of how colonial legacies may perpetuate inequalities in post-colonial autocracies, and challenges the characterization of private property rights as a prerequisite for development and democratization.