I address the question "when do peasants on collectively owned land demand private titles?" by analyzing a land titling program in Mexico. I argue Mexico’s "punishment regime" in the 20th century influences the capacity of peasants to invest in a private title in the 21st century. Where commercial farmers were more powerful, the state issued fewer land grants to peasants and invested in public goods to capture electoral support from commercial farmers. Fewer peasants received land in these areas, but those who did had access to public goods that reduced socioeconomic marginalization and increased their capacity to invest in a private title. Using a technique called causal mediation analysis, I show that a higher percentage of arable land granted to the peasant sector during the 20th century directly reduces the likelihood of land privatization in the 21st century, and indirectly reduces privatization through farm productivity and human development levels.