This article first examines Osama bin Laden in the context of Islam, al-Qaeda, and other extremist ideologies. The analysis critiques his use of collective guilt to justify killing innocent people and his misuse of Islam as a rationale for terrorism, highlighting the extent of his bigotry and paranoia. Next, the theme of humiliation is discussed at both the cultural and the personal level. It is hypothesized that bin Laden utilized violence to overcome his humiliation and damaged masculinity. Finally, his ideology, terrorist acts, and behavior within his family are discussed in the context of Theodore Millon’s work on personality disorders, noting avoidant, compulsive, masochistic, sadistic, paranoid, antisocial, and narcissistic traits. The article was published in Aggression and Violent Behavior.