Since the Second World War, many analysts agree that the influence and power of the United States’ commander in chief has grown substantially. This trend of presidential empowerment continues in the Post-Cold War presidency and into the aftermath of the terrorist strikes on September 11, 2001, as commanders in chief have continued to assert wide and nearly unilateral war authority. Few members of congress have challenged this movement, and in fact, a number have worked to advance an even more empowered chief executive. Standing apart from this trend is former member of Congress Dennis Kucinich (D-Oh.), who served in Congress from 1997 to 2013. Over the course of his sixteen years in the House of Representatives, Kucinich, in a non-partisan fashion, challenged his commanders in chief and called upon members of Congress to assert their constitutional war powers to check presidents in their military actions. This article examines Congressman Kucinich’s legacy related to war powers, and argues that Kucinich consistently made the case for an actively engaged Congress on all decisions related to the use of force abroad. Indeed, since Kucinich’s departure, the Obama administration has waged its own new war in the Middle East, striking hundreds of targets on the Islamic State in Iraq and the Levant (ISIL). Senior congressional leaders continue to find reasons not to bring a war resolution up for a vote.