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It is well-established in the research literature that authoritarianism leaves behind cultural and institutional legacies that make it difficult for countries to develop robust democratic regimes and the rule of law. This insight, however, cannot explain why some countries that experienced authoritarian regimes are more successful than others in building strong and effective judicial systems in the post-authoritarian stage. I answer this question by studying Mexico (1934-2008) and Spain (1939-1978) in comparative-historical perspective. Franco’s military dictatorship in Spain was a harsher form of authoritarianism than Mexico’s PRI-regime, with Franco exercising a degree of control over the judiciary unlike anything the PRI ever achieved. As a result, one would expect Spain’s path toward the rule of law to have been more troubled than Mexico’s. And yet, the exact opposite is true. While Mexico struggles to build a minimally effective judicial system, in Spain the judicial protection of civil and political rights is practically indistinguishable from older, more established democracies. Why? Using archival data collected at various archives in Spain and Mexico, I argue that the key to answering this question lies in understanding the specific mechanisms through which the executive power in each country controlled courts and judges during the authoritarian period. These mechanisms bequeathed different types of organizational structures and bureaucratic cultures to the judicial systems of these countries in the post-authoritarian era, thereby defining the political and institutional context in which legal reforms of the judiciary were attempted. This research shows how the longstanding conceptual opposition between authoritarianism and democracy obscures our understanding of the multiple paths countries can take to build strong judiciaries. It also brings into sharp relief the modernizing effects of certain authoritarian legal structures. In doing so, it makes theoretical contributions to our understanding of the paradoxical institutional origins of the rule of law.