Existing theories of regime transitions suggest that new democracies are more prone to political violence than consolidated democracies. We contend that this risk varies based on the political legacy of the new regime. Specifically, we argue that the prior authoritarian regime influences the risk of conflict in new democracies by shaping the nature of the post-transition political environment. In democracies following military rule, the former autocratic leadership often remains an active political force in the new regime. The continued presence of a materially powerful opposition creates a division in the new regime, increasing the risk of conflict by: (i) complicating efforts to consolidate democratic rule and (ii) signaling potential political opportunity to would-be rebels. In line with our argument, we find that only those new democracies emerging from military rule are more likely to experience civil conflict compared with consolidated democracies. These findings have implications for democracy promotion and conflict prevention efforts, suggesting that democratization is not always associated with an increased short-term risk of conflict as is currently assumed.