In nonviolent mass protests against dictators, the military is the ultimate arbiter of regime survival. Drawing on a global survey of forty “dictator’s endgames” from 1946 to 2014, this essay examines how dictators and their militaries respond to popular protests, and what the consequences are in terms of the survival of authoritarianism or the emergence of democracy. The authors argue that the type of the authoritarian regime and the military’s legacy of human rights violations go a long way in explaining whether a military will employ violence against the protesters or defect from the ruling coalition.