Increasing inequality across the globe has revived a century-old debate relating political legitimacy to redistributive policies. Advanced democracies and entrenched autocracies alike have seen the gap between the “haves” and “have-nots” widen since the Third Wave of Democratization in the early 1990s, underscoring the importance of unpacking the relationship between redistributive economic policy and regime legitimacy. The literature on redistribution in MENA is dominated by rentierist explanations that predicate political legitimacy on social benefits financed through aid or oil rents. Comparative political economy construes redistribution in democratic contexts as a social good that citizens demand from governments in exchange for political stability. While these works provide a basic rationale for redistribution, they do not explain why authoritarian governments choose to redistribute and what impact this choice has on a regime's capacity to rule legitimately. In this paper, I show that governments that redistribute land cultivate less political legitimacy than those who do not. While income redistribution is rare in MENA states, capital-intensive redistributive policies in the form of land redistribution is a common feature across the Maghreb and Levant in the post-independence period. I advance the hypothesis that regimes are more likely to redistribute land to expropriate the incumbent landowning elite. In cases where landowners are part of the ruling coalition, redistributive policies increase political uncertainty and undermine elite coalitions, decreasing the regime's legitimacy. Using an original database detailing all instances of land reform in sovereign MENA states since 1900, I present statistical models that suggest land redistribution negatively impacts regime legitimacy in the absence of elite divisions. These results are robust to two measures of political legitimacy: regime duration and political stability. Historical case studies of land redistribution in Jordan, Tunisia and Syria substantiate this quantitative finding. This study contributes to the MENA and global literatures on political legitimacy with new empirical evidence that clarifies the relationship between economic policies and political order.