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How Anwar al-Awlaki Came to Be Targeted With an Armed Drone

Benjamin Wittes
Wednesday, September 9, 2015, 9:30 AM

Objective Troy: A Terrorist, a President, and the Rise of the Drone

By Scott Shane

Published by Tim Duggan Books (2015)

Nearly three years ago, testifying before a congressional hearing, I observed that “the [Anwar] Al-Awlaki case will be someday the subject of a truly wonderful book. It’s a very complicated and interesting history.”

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Objective Troy: A Terrorist, a President, and the Rise of the Drone

By Scott Shane

Published by Tim Duggan Books (2015)

Nearly three years ago, testifying before a congressional hearing, I observed that “the [Anwar] Al-Awlaki case will be someday the subject of a truly wonderful book. It’s a very complicated and interesting history.”

Around the same time, a journalist friend of mine asked me to suggest a counterterrorism-related book project, and I suggested Al-Awlaki.

The story, I argued, bridges the entire period of contemporary American counterterrorism. Al-Awlaki, then an imam in the United States, knew some of the 9/11 hijackers, and there was a continuing mystery as to whether he may have played a role in the September 11 attacks. Yet his subsequent demise at the business end of a Predator drone reflected the rise of the the Obama administration’s major counterterrorism initiative. At different times, Al-Awlaki played the moderate Muslim leader, and he later played the radical Muslim leader and terrorist operative. Was his story of that of the sleeper agent feigning moderation? Or was it the story of a moderate hounded by the US government into radicalism?

And then there’s the matter of Al-Awlaki’s US citizenship. For whatever else his story is, Al-Awlaki’s story is also one of the limits of the relationship between citizen and government. It’s the story of what it takes to dissolve that relationship, and when—if ever—it is legitimate for a government to hunt one of its citizens to the ends of the earth and incinerate him, and what an individual has to do to warrant that

The day I predicted in my congressional testimony has arrived, though not at the hands of the journalist to whom I suggested the project. And Scott Shane of the New York Times opens his remarkable new book on Al-Awlaki with a very similar argument for the subject’s importance to the one I advanced:

This book grew from an obsession with three questions: Why did an American who spent many happy years in the United States, launched a strikingly successful career as a preacher, and tried on the role of bridge builder after the 9/11 attacks end up dedicating his final years to plotting the mass murder of his fellow Americans? How did a president and former professor of constitutional law, who ran against the excesses of George W. Bush’s counterterrorism programs and vowed to forge a new relationship with the Muslim world, come to embrace so aggressively the targeted killing of suspected terrorists, sometimes with the emphasis on “suspected”? And what was the role of the technology that would link Obama and Awlaki, the armed drone, which was created to meet the challenge of terrorism, killed some very dangerous people, got oversold and overused, and further poisoned relationship with Muslims worldwide?

. . .

The life of Anwar al-Awlaki, who knew two of the future 9/11 hijackers at his San Diego mosque in the months before their plot unfolded, and who was killed a decade later after a high-tech, no-holds-barred manhunt, seemed to encompass the era. His story spanned four presidencies, raised in pointed ways the dangers of both terrorism and the reaction to it, and seemed emblematic of the defining conflict between America and an extreme school of Islam.

Shane’s book, Objective Troy: A Terrorist, A President, and the Rise of the Drone, takes on both the bureaucratic and military story of the rise of the drone program and Obama’s investment in it and the human story of Al-Awlaki’s own development and transformation. Objective Troy is a gripping read. It’s also one of the more informative accounts of the development of American counterterrorism—and the development of America’s terrorist enemies—that I’ve read in a while. Shane has done a great deal of reporting in a great deal of depth, from the high echelons of the White House to Yemeni friends and family of Awlaki. It’s a very impressive work across a number of axes. And to my mind, at least, it unravels some of the important mysteries about one of the more mysterious figures to arise in the post-9/11 era.

What Shane does so well in this book is to untangle several distinct narrative threads that cumulatively make the Al-Awlaki case both objectively important and subjectively fascinating. There’s the character of the man himself. Who was he really, and how and why did he radicalize—assuming he was not always a terrorist plotter? There’s the story of the development of the drone program, and Obama’s reliance on it. There’s the story of the controversy over the targeting of US citizen. There’s the story of Al-Awlaki’s impact on many English-speaking Muslims around the world, for whom he became a particularly tantalizing voice of radicalism. And there’s the story of the manhunt: how Al-Awlaki went from a guy the FBI could visit and chat with—and who could lead prayers at the Pentagon and take calls from any number of journalists—to someone who taunted American intelligence while the ACLU litigated to prevent his targeting.

Shane does an excellent job telling these stories—both disaggregating them from one another and weaving them back together. He does a particularly good job on the human side of the story: the development of Al-Awlaki’s character and thought and the impact of the whole episode on his family. Shane had the cooperation of the preacher’s father, brother, and uncle, so he is able to describe in considerable depth both the family’s efforts to restrain Al-Awlaki and its efforts to protect him.

The tragedy for the family actually went well beyond the killing of Al-Awlaki himself, because Al-Awlaki’s eldest son—then 16 years old—was also killed in a separate strike a few weeks later, after abandoning the family house to go seek out his father. However sympathetic with the Al-Awlaki strike one may be, and I have no problem with Obama’s decision, it is impossible not to sympathize with the man’s family after what these people have been through. One of the interesting features of the book is how attractive members of Al-Awlaki’s family are.

Shane, in general, does a very good job making people confront the hardest arguments and facts for whatever position they may hold. For those enthusiastic about drone strikes, he is candid about how imprecise—even incompetent—some of them have been and how many civilians have lost their lives as a result. Abdurrahman Al-Awlaki is not the only kid who died. Conversely, for those who whitewash Al-Awlaki as just a radical preacher, he lays out the evidence unsparingly that by the end, at least, he was a lot more than that. He was an operational terrorist committed to killing Americans. And for those who reflexively oppose drone strikes, his story highlights why drones hold such an attraction for Obama: because they let the US reach dangerous people it couldn’t otherwise get without resorting to major ground operations.

The book’s particular strength, at least in my opinion, is its depiction of Al-Awlaki. Shane makes a persuasive case that he probably was not involved in any way with the 9/11 plot, though he does not whitewash some suggestive facts. He also makes a persuasive argument that Al-Awlaki’s sudden abandonment of the United States in 2002 probably had little to do with jihadism or ideology and more to do with prostitution. Al-Awlaki had a bit of habit of using prostitutes, and his departure coincided with his discovery that the FBI knew about it. His radicalization, Shane’s story suggests, follows this period and may have been more a result of his leaving the U.S. than a cause of it.

Shane does not resolve the mystery of Al-Awlaki’s past completely. Those who believe that he had advance knowledge of 9/11—or played some more active role in it—have tantalizing bits to hang on. But I found Shane’s account of his emotional and intellectual trajectory pretty compelling. He was a man who could have taken any of several very different roads. He became more radical as his career options grew leaner and his following grew larger, angrier, and hungrier.

I have three relatively minor criticisms of Objective Troy.

The first is that one of the author’s conceits for the book seems to me a bit silly. In his prologue, Shane juxtaposes Obama and Al-Awlaki, as though theirs are parallel stories and developments:

When the Awlaki family strolled the streets of Manhattan on the way west that idyllic summer, a lanky, brown-skinned young man a decade older than Anwar was walking the same crowded sidewalks. . . .

Like Anwar al-Awlaki, Barack Obama had been born in the United States to a secular-minded foreign father of Muslim background who had come on scholarship to further his education. Like young Anwar, he had left the United States as a child and lived in a Muslim country. . . . Obama would embrace America and ultimately vault to the pinnacle of power, his election as president in 2008 sending a message of empowerment and possibility that resonated with millions overseas, including the Awlaki family. Awlaki would briefly sample American fame, becoming a national media star as a sensible-sounding, even eloquent cleric after 9/11 when Obama was still an unknown. Later, he would gradually and then decisively reject America and finally devote himself to its destruction. The men would never meet, except virtually, clashing in the public battleground of ideas, where the cleric’s mastery of the Internet would serve his jihadist cause, and violently, when Obama dispatched the drones that carried out Awlaki’s execution.

This reads a little preciously to me. Al-Awlaki is not interesting because he has a few life experiences in common with Obama—or vice versa. And we don’t actually learn much about America from these two men’s divergent reactions to it.

The conceit might work better if, in fact, Obama were a Muslim, so one could juxtapose their experiences as, in some sense, representative of different American Muslim reactions to the United States. But the overheated imagination of Obama’s critics aside, he isn’t a Muslim, and nothing about Obama represents the experience of American Muslims. As such, the parallels between the two men just aren’t interesting enough to be interesting. Fortunately, this theme doesn’t return all that often in the book, and when it does, it isn’t especially obtrusive.

The second problem is that Shane’s narrative sometimes makes the Al-Awlaki case seem a little harder than it really was—at least to officials within the government. He makes a lot, for example, of how ruling on the legality of the killing put David Barron and Martin Lederman—the two OLC lawyers who had to opine on it—in a difficult position. Both were severe critics of the Bush era approaches to counterterrorism, after all. And now they were defending robust government counterterrorism action.

But here, I fear, Shane’s admirable reporting tells a slightly different story. As other lawyers in the government reviewed the matter, he writes, the group “recognized the unprecedented nature of the case and discussed it at length, debating the fine points of the law and discussing whether capture might be possible. But in the end, there was no dissent.” Nobody doubted that “killing Awlaki would be legal and constitutional.”

Obama himself put it succinctly, in Shane’s telling: “This is an easy one.”

Shane notes the disparity between the unanimity on the killing in government and the more mixed perceptions outside of it. And he also notes that people outside of government tend to offer different views of the strike when he describes the evidence of what Al-Awlaki was up to than when he doesn’t. But at the end of the day, I fear that Shane may make the matter seem harder than it really is, at least legally speaking. If there is any merit at all to the United States’ view of the conflict with Al Qaeda, then surely Anwar Al-Awlaki—a man who, by Shane’s own account, was playing a leadership role in attempted attacks against the United States in a conflict authorized by Congress—was a legal target.

My final quibble with Shane’s book involves a minor sin of omission: In a long narrative about the case, he never once mentions an important option available to Al-Awlaki. Long before Al Awlaki was killed, I wrote of the debate over his being placed on the “kill list”:

The idea that Anwar al-Alauqi is being targeted for death and has no means of availing himself of his rights as a U.S. national is wrong. Like the hostage-taker, he has a remedy that will ensure his safety and give him the opportunity to defend himself: He can turn himself in. He can knock on the door of any U.S. consulate and say, "I hear you guys are looking for me." No special forces guys, Predator drones, or air strikes are going to take him out if he does this. In other words, this situation is, in conceptual terms, a fairly close analogue to the one in which cops surround a building and say, "Come out with your hands up or we'll shoot."

Shane never mentions that Al-Awlaki had the option of surrender. He makes clear that the preacher knew he was wanted. He makes clear that he had no regard for the US justice system. Yet he still falls into the trap of describing Obama as executing him without charge or trial and without any possibility of due process. It bears mention that had Al-Awlaki wanted due process, it was there for the taking. It was precisely because he didn’t wish to avail himself of legal processes—and desired to plot the deaths of Americans from the Yemeni mountains—that the drone became an attractive, and perhaps the only, option for Obama.

These are, at the end of the day, minor gripes. Shane has written an excellent book—one that looks at several big topics through the lens of what seems, at first glance, to be the narrow story of the strange death and stranger life of a single man. Given the number of people who continue to be inspired by Al-Awlaki’s words, it’s a story that—the drone that killed him notwithstanding—will be with us for a long time to come.

Benjamin Wittes is editor in chief of Lawfare and a Senior Fellow in Governance Studies at the Brookings Institution. He is the author of several books.

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