Anwar al-Awlaki’s youngest brother, Ammar, was nothing like him. While Anwar embraced a radical interpretation of Islam and preached jihad against the United States, Ammar was pursuing a career at an oil company in Yemen. Ammar was Canadian-educated and politically well connected. He dressed in blue jeans, wore hip Armani eyeglasses and sported a goatee. His hair was slicked back, and he had the latest iPhone. In February 2011, Ammar told me, he was in Vienna on a business trip. He had just returned to his hotel after sampling some of the local cuisine with an Austrian colleague when the phone in his room rang. “Hello, Ammar?” said a man with an American accent. “My wife knows your wife, and I have a gift for her.”

Ammar went down to the lobby and saw a tall, thin white man in a crisp blue suit. They shook hands. “Can we talk a bit?” the man asked, and the two sat down in the lobby. “I don’t actually have a gift for your wife. I came from the States, and I need to talk to you about your brother.” 

“I’m guessing you’re either FBI or CIA,” Ammar said. The man smiled. Ammar asked him for identification. 

“Come on, we’re not FBI, we don’t have badges to identify us,” the man said. “The best I can do is, I can show you my diplomatic passport…. Call me Chris,” the American added.

“Was that your name yesterday?” Ammar replied.

Chris made it clear that he worked for the CIA. He told Ammar that the United States had a task force dedicated to “killing or capturing your brother”—and that while everyone preferred to bring Anwar in alive, time was running out. “He’s going to be killed, so why don’t you help in saving his life by helping us capture him?” Chris said. Then he added, “You know, there’s a $5 million bounty on your brother’s head. You won’t be helping us for free.”

Ammar told Chris that he didn’t want the money, that he hadn’t seen Anwar since 2004 and had no idea where he was. The American countered, “That $5 million would help raise [Anwar’s] kids.”

“I don’t think there’s any need for me to meet you again,” Ammar told Chris. Even so, the American told Ammar to think it over, perhaps discuss it with his family. “We can meet when you go to Dubai in two weeks,” he said. Ammar was stunned: his tickets for that trip had not yet been purchased, and the details were still being worked out. Chris gave Ammar an e-mail address and said he’d be in touch.

Ammar returned to Yemen and talked to his mother. “You stop it. Don’t even reply to them, don’t contact them again,” she said. “Just stop.” When Chris began e-mailing him after their meeting, Ammar didn’t respond.

* * *

On May 2, 2011, the night President Obama informed the world that Osama bin Laden had been killed by a team of Navy SEALs in Pakistan, thousands of Americans poured into the streets in front of the White House and in New York’s Times Square, chanting, “USA, USA, USA!”

The families of people killed on 9/11 spoke of bin Laden’s death bringing closure. But the Al Qaeda leader’s demise breathed new life into Washington’s global “war on terror.” The elite Joint Special Operations Command (JSOC), once shrouded in secrecy, became a household name overnight. The Disney Corporation tried to trademark the term “SEAL Team Six,” and Zero Dark Thirty, a high-profile Hollywood film, was hastily rewritten to focus on the operation; the filmmakers were even given access to sensitive material.

While the battle over leaks concerning the operation—as well as the various contradictory stories on how bin Laden was killed—raged in the media, the White House was deeply immersed in planning more lethal operations against so-called “High Value Targets.” Chief among these was Anwar al-Awlaki, an American citizen of Yemeni descent born in Las Cruces, New Mexico. 

Three days after Obama’s news conference on bin Laden, the president’s counterterrorism team presented him with an urgent intelligence update on Awlaki. Along with signals intercepts by JSOC and the CIA and “vital details of Awlaki’s whereabouts” from Yemeni intelligence, the White House now had what it believed was its best shot to date at killing the radical cleric, whose fiery speeches denouncing the United States—and praising attacks on Americans—had placed him in the cross-hairs of the US counterterrorism apparatus. 

US military aircraft were at the ready. Obama gave the green light. JSOC would run the operation. A Special Ops Dragon Spear aircraft mounted with short-range Griffin missiles blasted into Yemeni airspace, backed by Marine Harrier jets and Predator drones, and headed toward Shabwah Province. A Global Hawk surveillance aircraft would hover above to relay a live feed back to the mission planners.

* * *

Anwar al-Awlaki gives a religious lecture in an unknown location in this still image taken from video released by Intelwire.com on September 30, 2011. Reuters/Intelwire.com   On the evening of May 5, Awlaki and some friends were driving through Jahwa, in rural southern Shabwah, when their pickup truck was rocked by a massive explosion nearby, shattering its windows. Awlaki saw a flash of light and believed that a rocket had been fired at their vehicle. “Speed up!” he yelled at the driver. Awlaki looked around the truck and took stock of the situation. No one was hurt. The back of the pickup was filled with canisters of gasoline, yet the vehicle had not exploded. Alhamdulillah, Awlaki thought, according to his detailed account of the incident that later appeared in Inspire, the English-language magazine published by Al Qaeda in the Arabian Peninsula (AQAP). “Praise God.” He called for help.

While Awlaki and his colleagues scrambled to get away from what they thought was an ambush, JSOC planners watched via satellite as his truck emerged from the dust clouds that the Griffin missile had caused. They’d missed—there had been a malfunction in the targeting pod, and the missile’s guidance system was unable to keep a lock on Awlaki’s vehicle. It would now be up to the Harriers and the drones. Strike two: a massive fireball lit up the sky. Just as the celebrations at JSOC were about to begin, the mission’s planners watched in shock as the truck emerged once again from the smoke. Its back bumper had been damaged, but the truck was on the run. The Harriers were running low on fuel and had to abandon the mission. The third strike had to come from  one of the drones. Awlaki peered out the window, looking for the perpetrators of the ambush. It was then that he saw it: a drone hovering in the sky. As smoke and dust engulfed the area, Awlaki told the driver not to head toward any populated areas. They pulled into a small valley with some trees.

Two brothers, Abdullah and Musa’d Mubarak al Daghari, known among the members of AQAP as the al Harad brothers, were speeding to Awlaki’s rescue. As the drone hovered overhead, the US personnel running the op could not see what was happening below. A former JSOC planner, who read the after-action reports on the strike, told me that the mission had satellites that provided only “top-down imagery.” With such satellites, he said, “You’re looking down at ants moving. All they saw were vehicles, and the people in the vehicles were smart.” Dust, gravel, smoke and flames had shielded the High Value Target. The Harad brothers quickly marshaled Awlaki and his driver into their Suzuki Vitara SUV and took Awlaki’s vehicle. They gave Awlaki directions to a mountain area where he could take shelter. Awlaki hastily said goodbye and sped off in the Suzuki. The Harad brothers then headed in the opposite direction, driving in the truck the Americans had tried to blow up moments earlier.

As the two vehicles took off in opposite directions, the Americans running the operation had to decide which one to follow. They stuck with Awlaki’s truck. Awlaki looked up and saw the drones still hovering. He managed to make it to the mountains. From there, he watched as another round of missiles shot out of the sky and blew up the truck, killing the Harad brothers.

As JSOC celebrated what it thought was a successful hit, Awlaki performed his evening prayers and reflected on the situation. That night, he later recalled, had “increased my certainty that no human being will die until they complete their livelihood and [reach their] appointed time.” He fell asleep in the mountains.

As news spread of the attack, anonymous US officials confirmed that the strike had been aimed at Awlaki. And for a time, they thought they had accomplished the mission. The US drone operators “did not know that vehicles were exchanged and resulted in the wrong people dying and [that] Awlaki [was] still alive,” a Yemeni security official told CNN.

The Americans who were after Awlaki were not deterred by the failure of the strike in Shabwah, and thanks to intensive intelligence gathering, they soon would have another chance. “I want Awlaki,” President Obama reportedly told his counterterrorism team. “Don’t let up on him.”

In April 2011, Ahmed Abdulkadir Warsame, a Somali man with alleged links to his country’s militant Islamic group Al Shabab, was captured by JSOC forces in the Gulf of Aden. He was taken to a military brig aboard the USS Boxer, where Warsame was held incommunicado for more than two months before being transferred to New York and indicted on charges of conspiracy and providing material support to Al Shabab and AQAP. Warsame had recently met with Awlaki, and his interrogation sessions in JSOC’s custody, along with his seized computers and drives, yielded intelligence about the latter’s movements in Yemen.

* * *

Abdulrahman al-Awlaki, the oldest son of Anwar al-Awlaki, was born in Denver. Like his father, he spent the first seven years of his life in the United States, attending American schools. After he moved to Yemen with his family, his grandparents—Anwar’s mother and father—played a major role in his upbringing, particularly after Anwar went underground. Anwar “always thought that it is best for Abdulrahman to be with me,” Anwar’s father, Nasser al-Awlaki, told me. Anwar believed that his wife and children “should not be involved at all in his problems.” 

Abdulrahman admired his father and had even chosen Ibn al Shaykh, “Son of the Sheik,” as his Facebook user name. But Abdulrahman was not his father; he loved hip-hop music and Facebook and hanging out with his friends. They would take pictures of themselves posing as rappers, and when the Yemeni revolution began, Abdulrahman wanted to be a part of it. As massive protests shook Yemen, he would spend hours hanging out in Change Square with the young, nonviolent revolutionaries, sharing his vision for the future and, at times, just goofing off with friends. But as the revolution continued and the government was brought to the verge of collapse, Abdulrahman decided to follow his urge to see his father.

One day in early September, Abdulrahman woke up before the rest of the house. He tiptoed into his mother’s bedroom, took 9,000 Yemeni rials—roughly $40—from her purse, and left a note outside her bedroom door. He then snuck out the kitchen window and into the courtyard. Shortly after 6 am, the family’s guard saw the boy leave but didn’t think anything of it. It was Sunday, September 4, 2011, a few days after the Eid al-Fitr holiday marked the end of the holy month of Ramadan. Nine days before, Abdulrahman had turned 16.

A short while later, Abdulrahman’s mother woke up. She started to rouse his siblings for morning prayers and then went to wake him, but Abdulrahman was not in his bedroom. She called for him and, while searching the house, found his note. In it, he apologized for leaving without telling her and said that he missed his father and wanted to find him. He also said he was sorry for taking the money. “When his mother told me about the letter, it was just like a shock for me,” Abdulrahman’s grandmother Saleha told me. “I said, ‘I think this will be just like bait for his father.’” The CIA, she feared, “might find his father through him.” The family called around to Abdulrahman’s friends, but he had already boarded a bus at Bab al Yemen, in the old city in Sana’a. His destination was Shabwah, the family’s home province and the scene of repeated US airstrikes aimed at killing his father.

* * *

By early September, however, US surveillance aircraft had pinpointed Anwar al-Awlaki’s location far from Shabwah—at a small house in Khashef, a village in Jawf about ninety miles northeast of Sana’a. Villagers began seeing drones hovering in the skies above. Washington’s drone war had kicked into full gear in Yemen, so the presence of the aircraft was not particularly out of the ordinary. But what the villagers did not know was that the White House’s counterterrorism teams were watching one specific house—watching and waiting. Once they got a lock on Awlaki’s coordinates, the CIA deployed several armed Predator drones from its new base in Saudi Arabia and took operational control of some JSOC drones launched from Djibouti as well. The plan to assassinate Awlaki was code-named Operation Troy. The name implied that the United States had a mole leading its forces to Awlaki.

As the Americans surveilled the house where Anwar was staying in Jawf, Abdulrahman arrived in Ataq, Shabwah. He was picked up at the bus station by his relatives, who told him that they did not know where his father was. The boy decided to wait in the hope that his father would come to meet him. His grandmother called the family he was with in Shabwah, but Abdulrahman refused to speak with her. “They said, ‘He’s OK, he’s here,’ but I didn’t talk to him,” Saleha recalled. “He tried to avoid talking to us, because he knows we will tell him to come back. And he wanted to see his father.” Abdulrahman traveled with some of his cousins to the town of Azzan, where he planned to await word from his dad.

At the White House, President Obama was faced with a decision—not of morality or legality, but of timing. He had already sentenced Anwar al-Awlaki to death without trial. A secret legal authorization had been prepared and internal administration critics sidelined or brought on board. All that remained to be sorted out was the day Awlaki would die. Obama, one of his advisers recalled, had “no qualms” about this kill. When the president was briefed on Awlaki’s location in Jawf and also told that children were in the house, he was explicit that he did not want to rule any options out. Awlaki was not to escape again. “Bring it to me and let me decide in the reality of the moment rather than in the abstract,” Obama told his advisers, according to author Daniel Klaidman. Although scores of US drone strikes had killed civilians in various countries around the globe, it was official policy to avoid such deaths if at all possible. “In this one instance,” an Obama confidant told Klaidman, “the president considered relaxing some of his collateral requirements.”

* * *

Awlaki had evaded US drones and cruise missiles for at least two years. He rarely stayed in one place more than a night or two. This time was different. For some reason, he had stayed in the same house in Khashef much longer, all the while being monitored by the United States. Now the Americans had him clean in their sights. “They were living in this house for at least two weeks. Small mud house,” Nasser said he was later told by the locals. “I think they wanted to make some videotape. Samir Khan was with him.” 

On the morning of September 30, 2011, Awlaki and Khan, a young Pakistani-American from North Carolina who is believed to have been the editor of Inspire, finished their breakfast inside the house. US spy cameras and satellites broadcast images back to Washington and Virginia of the two men and a handful of their cohorts piling into vehicles and driving away. They were headed toward the province of Marib. As the vehicles made their way over the dusty, unpaved roads, US drones, armed with Hellfire missiles, were dispatched to hunt them down. The drones were technically under the command of the CIA, though JSOC aircraft and ground forces were poised to assist. A team of commandos stood at the ready to board V-22 helicopters. As an added measure, Marine Harrier jets scrambled in a backup maneuver.

Six months earlier, Awlaki had narrowly avoided death by US missiles. “This time eleven missiles missed [their] target but the next time, the first rocket may hit it,” he had said. As the cars sped down the road, Awlaki’s prophecy came true. Two of the Predator drones locked onto the car carrying him, while other aircraft hovered as backup. A Hellfire missile fired by a drone slammed into his car, transforming it into a fireball. A second missile hit moments later, ensuring that the men inside would never escape if they had managed to survive. 

The Yemeni government sent out a text message to journalists. “The terrorist Anwar Awlaki has been killed along with some of his companions,” it read. It was 9:55 am local time. When villagers in the area arrived at the scene of the missile strike, they reported that the bodies inside the car had been burned beyond recognition. There were no survivors. Amid the wreckage, they found a symbol more reliable than a fingerprint in Yemeni culture: the charred rhinoceros-horn handle of a jambiya dagger. There was no doubt that it belonged to Anwar al-Awlaki.

On September 30, during a visit to Fort Myer in Virginia, President Obama stepped up to a podium and addressed reporters. “Earlier this morning Anwar Awlaki, a leader of Al Qaeda in the Arabian Peninsula, was killed in Yemen,” Obama declared. “The death of Awlaki is a major blow to Al Qaeda’s most active operational affiliate.” The president then bestowed upon Awlaki a label that had never been attached to him publicly before, despite all of his reported associations with Al Qaeda: “Awlaki was the leader of external operations for Al Qaeda in the Arabian Peninsula. In that role, he took the lead in planning and directing efforts to murder innocent Americans,” Obama asserted. 

While the White House and some leading national security officials assured journalists and the public that the process of targeting and killing Awlaki was lawful, the administration refused to make its evidence public. Some lawmakers—whose security clearances and committee assignments authorized them to review the kill process—alleged that they were not being sufficiently briefed by the White House. “It’s important for the American people to know when the president can kill an American citizen, and when [he] can’t,” Senator Ron Wyden told me. Wyden, a Democrat from Oregon, has served on the Senate Intelligence Committee since 2001 and often found himself at odds with the Bush administration over secrecy and transparency issues. Now, under a Democratic president, he found himself waging the same battles—and some new ones. Wyden said that he repeatedly asked the administration to provide its legal rationale for killing American citizens without trial, calling his attempts to extract this information ”an enormous struggle.” 

Nasser al-Awlaki believed that the US and Yemeni security forces could have arrested his son, but that they did not want to see Anwar stand trial and present a defense. It is also possible, Nasser suggested, that the United States did not want to give him a platform to spread his message more widely. “How is it that Umar Farouk, who tried to blow up the airplane, or Nidal Hasan, who actually killed those soldiers, how are they now having, let us say, a fair trial?” Nasser asked. “My son did not get that fair trial.”

* * *

Abdulrahman al-Awlaki.   As the Awlaki family mourned the death of Anwar, their attention turned to their grandson, Abdulrahman. He had gone to Shabwah to find his father, and now his father was dead.   After Abdulrahman heard the news of Anwar’s death, he called home for the first time and spoke to his mother and grandmother. “That’s enough, Abdulrahman. You have to come back,” his grandmother Saleha told him. “That’s it.” The conversation was brief. Abdulrahman said he would return home soon, but that he wanted to wait for the roads to clear. There were police checkpoints and fighting along the route, and he did not want to be detained or caught up in any violence.

As Abdulrahman mourned, the boy’s family members in Shabwah tried to comfort him and encouraged him to get out with his cousins. That was what Abdulrahman was doing on the evening of October 14. He and his cousins had joined a group of friends outdoors to barbecue. There were a few other people doing the same nearby. It was about 9 pm when the drones pierced the night sky. Moments later, Abdulrahman was dead. So, too, were several other teenage members of his family, including Abdulrahman’s 17-year-old cousin Ahmed.

Early the next morning, Nasser al-Awlaki received a phone call from his family in Shabwah. “Some of our relatives went to the place where [Abdulrahman] was killed, and they saw the area…. And they told us he was buried with the others in one grave because they were blown up to pieces by the drone. So they could not put them in separate graves,” Nasser told me. 

With the horror setting in that their eldest grandson had been killed just two weeks after their eldest child, Nasser and Saleha watched in disbelief as numerous news reports identified Abdulrahman as being 21 years old, with anonymous US officials referring to him as a “military-aged” male. Some reports intimated that he was an Al Qaeda supporter and that he had been killed while meeting with Ibrahim al-Banna, an Egyptian citizen described as the “media coordinator” for AQAP.

When I visited Nasser after Abdulrahman was killed, he showed me the boy’s Colorado birth certificate, which states that he was born in 1995 in Denver. “When he was killed by the US government, he was a teenager; he wasn’t 21. He wouldn’t have been able to enlist in the military in the US. He was 16,” Nasser told me. Days after the killing of Abdulrahman, the United States released a statement, as usual feigning ignorance about who was responsible for the strike, even though “unnamed officials” in the United States and Yemen had confirmed it. “We have seen press reports that AQAP senior official Ibrahim al-Banna was killed last Friday in Yemen and that several others, including the son of Anwar al-Awlaki, were with al-Banna at the time,” National Security Council spokesman Tommy Vietor told the press, in a statement that strangely cast Abdulrahman as something between an Al Qaeda associate and a hapless tourist. “For over the past year, the Department of State has publicly urged US citizens not to travel to Yemen and has encouraged those already in Yemen to leave because of the continuing threat of violence and the presence of terrorist organizations, including AQAP, throughout the country.”

While the Awlakis opposed Anwar’s killing and believed that the United States had exaggerated its claims about his involvement with Al Qaeda, Nasser told me that his family understood why the United States wanted Anwar dead. “My son believed in what he did,” Nasser said, “but I am really distressed and disappointed by the killing, the brutal killing, of his son. He did nothing against the US. He was an American citizen. Maybe one day he would have gone to America to study and live there, and they killed him in cold blood.”

The CIA later claimed that it did not carry out the strike, asserting that the supposed target, al-Banna, was not on the agency’s hit list. That led to speculation that the attack that killed Abdulrahman and his relatives had been a JSOC strike. According to The Washington Post, senior US officials acknowledged that “the two kill lists don’t match, but offered conflicting explanations as to why.” The officials added that Abdulrahman was an “unintended casualty.” A JSOC official told me that the intended target was not killed in the strike, though he would not say who that was. On October 20, 2011, military officials presented a closed briefing on the strike to the Senate Armed Services Committee. With the exception of the statements from anonymous officials, the United States offered no public explanation for the attack. The mystery deepened when AQAP released a statement claiming that al-Banna was still alive. The Awlakis began to wonder if perhaps Abdulrahman was, in fact, the target of the strike.

Senate majority leader Harry Reid, one of the handful of US lawmakers who would have access to intelligence on the strike, seemed to suggest that this was the case when asked about the killing of the two Awlakis and Samir Khan. “I do know this,” he said on CNN, “the American citizens who have been killed overseas…are terrorists, and, frankly, if anyone in the world deserved to be killed, those three did deserve to be killed.” 

Robert Gibbs, former White House press secretary and a senior official in President Obama’s 2012 re-election campaign, was also asked about the strike that killed Abdulrahman. “It’s an American citizen that is being targeted without due process of law, without trial. And he’s underage. He’s a minor,” reporter Sierra Adamson said. Gibbs shot back: “I would suggest that you should have a far more responsible father if they are truly concerned about the well-being of their children. I don’t think becoming an Al Qaeda jihadist terrorist is the best way to go about doing your business.”

While emphasizing that they were not prone to conspiracy theories, the Awlakis told me it was difficult to understand why Abdulrahman would have been killed, especially if al-Banna was not there. Who, then, was the target? “It is up to the US government to be sure about the kind of information they get before they take any action against anybody. So I don’t believe it was just an accident,” Nasser said. 

An anonymous US official later told The Washington Post that Abdulrahman’s killing was “an outrageous mistake…. They were going after the guy sitting next to him.” But no one ever identified who that was. As far as the family knows, their grandson was sitting with his teenage cousins, none of whom had an affiliation with Al Qaeda. Decisions on “targets, drones—these are made only by the highest US government authorities, the CIA and all that. Why did they specifically target these guys?” Nasser demanded. “I want answers from the United States government.”

The Obama administration would fight passionately to keep those answers secret, invoking the “state secrets” privilege repeatedly—just as George W. Bush had done throughout his eight years in office. 

A former senior official in the Obama administration told me that after Abdulrahman’s killing, the president was “surprised and upset and wanted an explanation.” The former official, who worked on the targeted killing program, said that according to intelligence and Special Operations officials, the target of the strike was al-Banna, the AQAP propagandist. “We had no idea the kid was there. We were told al-Banna was alone,” the former official told me. Once it became clear that the teenager had been killed, he added, military and intelligence officials asserted, “It was a mistake, a bad mistake.” However, John Brennan, at the time President Obama’s senior adviser on counterterrorism and homeland security, “suspected that the kid had been killed intentionally and ordered a review. I don’t know what happened with the review.”

Caitlin Hayden, a spokeswoman for the National Security Council, would not answer questions about the former official’s assertions, saying that she “can’t address specific operational matters and won’t go into our internal deliberations,” adding: “We cannot discuss the sensitive details of specific operations.” In an e-mail, she pasted a lengthy statement citing the public pronouncements of various US counterterrorism officials, much of which had already become part of the White House’s boilerplate response to any media inquiries regarding the drone strikes.

Brennan, who is now director of the CIA, recently answered an inquiry from the Senate Intelligence Committee on such after-strike reviews. When civilians are killed, Brennan said, “we not only take account of the human tragedy, but we also go back and review our actions.” Analysts “draw on a large body of information—human intelligence, signals intelligence, media reports, and surveillance footage—to help us make an informed determination about whether civilians were in fact killed or injured,” Brennan asserted in his written response. “In those rare instances in which civilians have been killed, after-action reviews have been conducted.” No such review of Abdulrahman’s killing has ever been made public.

The consensus that has emerged from various anonymous officials commenting on Abdulrahman’s killing was that it was a mistake. I asked the former senior administration official why, if that was the case, the White House didn’t publicly acknowledge it. “We killed three US citizens in a very short period,” he told me. “Two of them weren’t even targets: Samir Khan and Abdulrahman Awlaki. That doesn’t look good. It’s embarrassing.”

This article is adapted from Dirty Wars: The World Is a Battlefield, just published by Nation Books. If you like this article, vote for The Nation in this year's Webby Awards.