This is an article for a philosophy journal that examines the reasons why freedom and violence are often understood in symbiotic manner. The article engages notions of responsibility and the paradox of freedom to shed light on why expressions of freedom often, and inevitably, culminate into violence. In this article, the author analyses cases of freedom and violence in liberal and illiberal contexts through the lens of political philosophy, namely, critical works on freedom and responsibility by philosophers such as Thomas Nagel, Isaiah Berlin, Karl Popper, and Uwe Steinhoff, amongst others.