Since the death of Abu Bakr al-Baghdadi, there has been renewed discussion about the effectiveness of leadership decapitation as a counterterrorism strategy. As a strategy, members at all levels of the organizations are targeted, but much of the literature focuses only on the top leaders. The existing literature suggests that leadership decapitation is ineffective, pointing to the fact that Baghdadi’s death did not destroy Daesh. This research argues, when mid-level leaders are targeted, leadership decapitation is an effective counterterrorism strategy, as their deaths disrupt group activities. This research focuses on the impact that mid-level leaders have on group operational capacity, looking specifically at mid-level leaders with specialized skills, like explosives experts and operations planners. This paper focuses on the impact that strategic targeting of mid-level leaders has had on Al-Qaeda and Daesh from 2015 to 2020. Ultimately, the research finds that leadership decapitation is an effective counterterrorism policy, when mid-level leaders are targeted.