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This paper explores the puzzle of why the pastoral Maasai of Kajiado, Kenya, supported theindividualization of their collectively held group ranches, an outcome that is inconsistent withtheoretical expectation. Findings suggest that individuals and groups will seek to alter propertyrights in their anticipation of net gains from a new assignment, even as they seek to eliminatedisadvantages that were present in the status quo property rights structure. Heightenedperceptions of impending land scarcity, failures of collective decision making, the promise ofnew income opportunities and the possibility of accessing capital markets motivated individualsto support group ranch subdivision. More importantly individuals were confronted with adeclining security of tenure over their lands. Their supporting a transition to individual rightsalso represents a rational response anticipated to secure land claims against unauthorizedappropriations by both Maasai and non-Maasai elite. Given the differentiated structure of groupranch communities, the costs and benefits of property transformation were unevenly distributed.The political process yielded beneficial outcomes for those with access to decision making, whilecreating vulnerabilities for those with less access such as women, the youth and poor herders.