This dissertation addresses two questions regarding post-praetorian democratization and democratic development. First, it explains why some militaries bind democracy by imposing certain parameters on political contestation and popular sovereignty while others do not. Second, it explains why some civilians are more successful than others at establishing civilian supremacy over the military after the transition has completed. I theorize that militaries bind democratization when civilians lack credible commitments regarding the security of the military’s interests under democracy. Specifically, I argue that three factors generate credible commitments and boost the military’s confidence in civilians: trust with political parties, the institutionalization of the incumbent party, and the strength of the incumbent party. When incumbent parties hold the trust of the military, they can be expected to defend its interests. Yet militaries must expect the party will survive the transition and subsequent elections (institutionalization) and be strong enough to defend the military in the legislature and/or executive. Regarding the development of civilian supremacy, I argue that civilians can marginalize the political influence of the military following military rule if parties and the party system are institutionalized. Institutionalized parties have higher degrees of autonomy, stronger links to society, and independent fundraising capacity which allow them to check the political impulses of the military if they choose to. However, parties must also be able to coordinate against the military. This requires the party system to be stable with a low degree of fragmentation. To test these theories I use a mix of methods. I employ a comparative historical analysis and use qualitative data to track and compare the development of the key causal mechanisms outlined in the theories. I also use an original dataset on military-led democratization to conduct a large-n cross-national analysis of whether trust, party institutionalization, and party strength results in less bounded democracy.