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The existing literature on military effectiveness established the robust claim that democracies are more successful and effective in winning interstate wars. One mechanism that explains this relationship heavily draws upon the underlying effect of regime type on civil-military relations. Still, this relationship has not yet been explored systematically, and rigorous empirical research on this issue remains surprisingly scarce. In order to address this shortcoming, this study investigates the patterns of civil-military relations according to different regime types, that is, democracies and nondemocracies. More specifically, the authors examine whether and how democracies invest in coup-proofing, that is, strategies employed to prevent the military from seizing power. The main argument is derived from a principal-agent logic and claims that coup-proofing is both a relatively less attractive and necessary instrument for democratic principals. By analyzing newly compiled time-series cross-sectional data on states' coup-proofing efforts in 1975–1999, the core hypothesis is tested in a quantitative framework.