In 2001, Anwar al-Awlaki appeared to be a moderate American cleric with a gift for inspired preaching. He was the imam of a mosque near Falls Church, Virginia, and the Muslim chaplain at George Washington University. After the attacks of September 11, 2001, he was invited by Pentagon officials to Washington, DC, for several events, where he served as a representative of Islam. At the same time, he was studying in a doctoral program in human resource development at George Washington University that his father hoped that would credential him for a desirable position with Sanaa University or the Yemeni government (Shane 2015, 123). Yet in 2002, al-Awlaki left the United States and his budding career as an imam, and between 2004 and 2006 completely reinvented himself as one of militant jihad's most outspoken advocates. By 2010, he had been approved by the administration of US President Barack Obama for extrajudicial killing, which eventually occurred in a drone strike in 2011. What happened to turn al-Awlaki into a vociferous proponent of jihadist violence?

Some have suggested that al-Awlaki had always harbored sympathy for a militant brand of jihadism and that his decision to leave the United States was prompted by heavy-handed US surveillance of Muslims in Northern Virginia, where he lived, which stoked his fury and completed his radicalization (see Shane 2015, 102–104). But this narrative is probably incorrect. Although there were hints of jihadist sympathies earlier in life, al-Awlaki's turn to full-blown jihadism seems to have been precipitated by the imminent derailment of his career as a cleric in the United States, in 2002. According to Shane (2015, 118–119), al-Awlaki was planning to stay in the United States until March 2002, when he told his brother Ammar, “I was told that the FBI has a file on me, and this file could destroy my life.” Unbeknownst to most, al-Awlaki had a secret vice: he frequented prostitutes, meeting them most often in area motels.