It is well-documented that leaders' conceptual complexity can affect their decision-making, but what about its broader effects on political violence? While Hermann & Sakiev (2011) and Conway & Conway (2011) have examined terrorists' conceptual complexity before attacks, this study generates a more extensive analysis by examining weapon types and target types. This research explored the connection between a terrorist leader's level of conceptual complexity and the violent attacks their organizations commit, arguing that complexity lowers before an attack and after the 9/11 terrorist attacks. It employed a content analysis of Osama bin Laden's rhetoric from 1999 to 2003 to discern levels of conceptual complexity. Out of more than 150 relevant pieces of rhetoric, 15 speeches, interviews, and statements were hand-coded, then compared to the total number, type, and magnitude of terrorist attacks committed during the correlating time frames using data from the Global Terrorism Database. Results show that bin Laden's conceptual complexity levels rose before an attack and more than doubled after 9/11. The potential impact of this research is notable. At a theoretical level, it supports previous findings on terrorist complexity while providing a new dimension of weapon type and target type. However, it would have an equally significant impact at the professional level by providing a method to implement specific security policies according to identify trends. Thus, giving counterterrorism professionals another potential tool to prevent harm.