A DIFFERENT BREED

ON OCTOBER 3, 2009, FBI agents from the Chicago Joint Terrorism Task Force watched David Coleman Headley leave his apartment, a whitewashed, four-story brick building on the north side of Chicago. They were conducting twenty-four-hour surveillance on him, posting agents outside his apartment, monitoring his e-mail accounts, and listening to his phone conversations. Headley was a tier-one terrorist target for the FBI, worthy of their best agents. He was on his way to O’Hare International Airport to catch a flight to Philadelphia and then to meet with terrorists in Pakistan, including a senior al Qa’ida external operations leader.

A light rain fell on the city, blown by stiff southwest winds, as the temperature crept above 50 degrees. Chicago was still reeling from the failure earlier that week of its bid to host the 2016 Olympic Games, which eventually went to the Brazilian city of Rio de Janeiro. President Barack Obama, basketball superstar Michael Jordan, and television mogul Oprah Winfrey had led an intense lobbying push, but the effort had fallen just short. Headley would have seen the headlines, but he was consumed by far more pressing issues.

He was born Daood Sayed Gilani in Washington, D.C., on June 30, 1960. What impressed FBI agents most about him were his many clandestine identities. A handsome man, he could blend into different environments with ease. “Headley was a very different case for us,” said Art Cummings, “and he was more of an entrepreneur than Najibullah Zazi, Umar Farouk Abdulmutallab, and some of the more recent al Qa’ida attackers.”1 Philip Mudd agreed: “The case of David Coleman Headley, a Pakistani-American, reveals an ‘A-level’ plotter who operated in the United States.”2

Headley was full of contradictions. His mother, Serrill Headley, was an American born in Maryland, and his father, Sayed Salim Gilani, was a Pakistani diplomat born in India. When traveling in the United States, he was David Headley, a debonair businessman with slicked-back hair, a clean-shaven face, and a neatly pressed Armani suit. He told acquaintances that he was a consultant for First World Immigration Services, a company that offered immigration services to clients, though this was just a cover for his terrorist operations. Headley, who had two wives, also had a wandering eye. In a January 2009 e-mail to Tahawwur Rana, a colleague, he commented on the “sites” in Denmark during his travels: “Girls here are really hot. Just the both of us should come here minus our girlfriends to have a good time.”3

When he arrived in Pakistan, Headley became Daood Gilani. He slipped into a shalwar kameez, grew a beard, grasped a leather-bound copy of the Qur’an, and supported a Salafist interpretation of Islam. He even had different-colored eyes, one ice blue, the other deep brown. “He was a chameleon,” said his uncle, William Headley. “He could slide smoothly between worlds.”4

Earlier in 2009 an individual named Sajid Mir, a retired major in the Pakistan Army, sent an e-mail to Headley. Sajid was now a member of the Pakistani terrorist group Lashkar-e-Taiba, which had developed close relations with al Qa’ida. “I need to see you for some new investment plans,” Sajid wrote on July 3. American intelligence agencies believed this referred to a terrorist plot.5

In the decade after September 11, 2001, al Qa’ida and other major terrorist operatives had become more proficient at using coded language in their communications. Their counterintelligence capabilities had also improved, though not enough to prevent the FBI from monitoring Headley’s e-mail exchanges and phone conversations.

Headley responded by e-mail on July 8: “What do you want me to do. Where are you interested in making investments.”6 He sent another e-mail the same day: “I think when we get a chance we should revisit our last location again.”7

U.S. intelligence agencies assumed the two were discussing another terrorist attack in India. Headley had conducted much of the preoperational reconnaissance for the grisly November 2008 terrorist attack in Mumbai, taking photographs and video footage of most of the target sites, such as the grandiose Taj Mahal Palace hotel. Ten operatives trained by Lashkar-e-Taiba assaulted targets with firearms, grenades, and improvised explosive devices, killing more than 170 people and wounding hundreds more. The attack captivated the world’s largest media conglomerates, like CNN and Al Jazeera, who gave it twenty-four-hour coverage for several days.

Sajid e-mailed back on July 8 saying that Lashkar-e-Taiba had “some work for you over there too,” a likely reference to India. “Matters are good enough to move forward.”8

The next day Headley answered: “When you say ‘move forward’ do you mean in the North direction or towards [India]. Also in the future if we need to meet to discuss anything, do i have to come all the way over there or can we meet somewhere in the middle like Africa or middle east.”9

Sajid, who was based in Pakistan, responded on July 9 that he meant toward India.10 U.S. intelligence officials believed the “North” referred to yet another terrorist plot, this one targeting the Copenhagen, Denmark, offices of the newspaper Morgenavisen Jyllands-Posten. In 2005 the newspaper had published a series of controversial cartoons of the Prophet Muhammad, the most notorious of which showed the Prophet with a bomb in his turban. The cartoons triggered large-scale protests across the Muslim world and death threats against the cartoonists and several newspaper executives.

On July 10, Headley sent an e-mail back to Sajid asking for clarification. “I would like to know a few things if you can tell me,” said Headley. “What is the status with the Northern project, is it still postponed indefinitely?” As for India, Headley asked whether it was “for checking out real estate property like before, or something different and if so tell me what you can please.” Headley also inquired about the timeline. “Will i have to stay there continuously for a while, or back and forth like before.”11

“There are some investment plans with me,” Sajid responded later on July 10, indicating that he meant in India.12

Headley sent back an e-mail on July 18: “One very important thing I need to know please is that how long do you need me for, meaning how long should it take me to finish my work, in your opinion. And is it really urgent? Before it seemed that the Northern Project was really urgent.”13

Sajid responded on July 18 that the India project “may take somewhere between 2 to 4 weeks.”14

Headley replied on July 19 that “I think i can manage it.” He would be available in October.15

Art Cummings and others at the FBI worked frantically to piece together the various operations. The Copenhagen plot involved Ilyas Kashmiri, a senior al Qa’ida leader who was operations chief for the militant group Harakat ul-Jihad al-Islami (HUJI) and a good example of how some Pakistani militants floated between groups. A second plot looked like it would be another Lashkar-e-Taiba attack in India, only a year after the Mumbai attack. What disturbed U.S. agents most, however, was that Headley seemed to be freelancing for several international terrorist organizations and governments. Over the rest of the summer the FBI continued to track his movements, listen to his phone calls, monitor his e-mail accounts, and collect intelligence from human sources close to Headley and his colleagues.

Sensing the urgency of the situation and concerned that an attack might be imminent, the FBI arrested Headley on October 3 at O’Hare International Airport. The agents found a number of items in his checked luggage, including a photocopy of the front page of an August 2009 issue of the Morgenavisen Jyllands-Posten, a street guide for Copenhagen, a list of phone numbers that included those of known terrorists, and a book entitled How to Pray Like a Jew. Also contained in the luggage was a memory stick with approximately ten short videos of potential attack sites.16

Headley was part of a new breed in the third wave. He worked simultaneously for several groups with connections to al Qa’ida, although each group was generally unaware of his involvement with the others. In addition he had worked as an informant for the U.S. Drug Enforcement Administration until 2002, and several years later he had begun working for Pakistan’s spy agency, the Directorate for Inter-Services Intelligence. He was a suave, swashbuckling figure, and capturing him required an extensive hunt by the FBI and other U.S. intelligence agencies. They used a combination of human sources and technical collection methods in locations around the globe, from the gritty ethnic neighborhoods of north Chicago to India, Denmark, and the tribal areas of Pakistan.

Finding a Niche

In 1960, just a few months after Headley was born, his parents moved from Washington, D.C., to Pakistan. In 1966 they divorced, and his father, a diplomat and a poet, raised him in Pakistan. Headley attended elementary school in Karachi and moved on to high school at the Cadet College Hasan Abdal in Punjab Province, which prepared boys for Pakistan’s armed forces. He developed a love of Islam and an abhorrence of India at a young age. “I disliked them,” he acknowledged, referring to Indians, because they “dismembered Pakistan.” Headley was eleven years old at the height of the Indo-Pakistani war, which led to Bangladesh’s independence from Pakistan. During the hostilities, India’s air force conducted a bombing raid that hit his school.17

He may not have minded that his classes were canceled. Headley acknowledged that he was a “very bad” student. His relationship with his stepmother also had begun to deteriorate.18 At age seventeen he moved back to the United States to join his biological mother, who ran a bar called the Khyber Pass in Philadelphia. In 1985, Headley’s mother put him in charge of the bar, an odd place for a Muslim to work. Perhaps unsurprisingly, Headley began to drink. He chased women and eventually started to smuggle heroin from Pakistan to the United States to make money. In 1988 he was arrested in Germany by DEA agents for heroin possession and distribution, and was sent to U.S. federal prison.19 After his release he moved to New York City and opened a video rental business in 1996, but in 1997 he was arrested again for heroin possession and distribution.20 This was a pivotal moment for Headley as a Muslim.

“He became devout when he got arrested for drugs,” said his uncle, William Headley. “He made a commitment to Allah that if he got cleared of this, he would follow the life, and that he did.”21

After his release from prison, Headley agreed to become a paid informant for the DEA, providing information on drug-trafficking activities.22 He also began to strengthen his ties with extremist groups in Pakistan. In 2000 he briefly returned to Pakistan and began attending Lashkar-e-Taiba meetings, while still working for the DEA.

Initially formed in the 1980s in Pakistan by Hafiz Saeed, a former professor and anti-Soviet fighter educated in Saudi Arabia and Pakistan, Lashkar-e-Taiba is an Islamic fundamentalist organization devoted to liberating India-controlled Kashmir through violent means and placing all of Kashmir in Pakistan. After September 11, Lashkar-e-Taiba developed a more robust global presence that focused on fundraising overseas, proselytizing, and occasionally conducting operations. Its members subscribed to the Ahle Hadith school of Islamic thought, a strict Sunni sect with views similar to the Salafist views of al Qa’ida leaders.

Some Lashkar-e-Taiba and al Qa’ida officials had a strong bond dating back to the anti-Soviet war in Afghanistan. After the U.S.-backed overthrow of the Taliban regime, some Lashkar-e-Taiba officials aided al Qa’ida operatives fleeing into Pakistan. In March 2002, for instance, U.S. and Pakistani security forces captured al Qa’ida operative Abu Zubaydah at a Lashkar-e-Taiba safe house in Faisalabad.23

Headley found speeches by Hafiz Saeed particularly stirring. In 2000 he attended a speech by Saeed along with two hundred other supporters at a house in the Model Town section of Lahore. “One second spent conducting jihad,” Saeed told the packed audience, is “superior to 100 years of worship.”24

According to several people who knew him, including his uncle William, Headley began to radicalize around this time.25 He was searching for an anchor in life and increasingly found it in a network of Pakistani militants. Headley supported Lashkar-e-Taiba’s ideology and commitment to fight India and volunteered to join the organization. In December 2001 he returned to Pakistan, and Lashkar-e-Taiba put him through a series of five training courses. The first, which lasted for three weeks, focused on indoctrinating operatives with Lashkar-e-Taiba’s ideology. Subsequent courses covered Qur’anic studies, weapons training, intelligence skills (such as setting up safe houses and surveillance), and antiterrorist training.26 By 2004, Headley had completed his training, and he begged to be deployed to Kashmir to fight Indians. But Zakir Lakhvi, who was responsible for Lashkar-e-Taiba’s military operations and was generally known as Zaki, had a different idea.27

“There was something better,” Zaki explained, “to do in the future.”

But Headley kept pushing. He was an American citizen, he told Zaki, and had spent considerable time there. He suggested that he could obtain a new passport “to make it easy to enter India undetected.”

Zaki was intrigued. “There were a lot of Pakistanis who had U.S. passports,” he responded, “but what was the place of birth, was it Pakistan or America?”

Headley’s answer left Zaki breathless. “It was Washington,” Headley affirmed.28

Headley suddenly became a critical recruit for Lashkar-e-Taiba. His name, Daood Sayed Gilani, sounded too Pakistani and would raise suspicions by Indian intelligence agents. He had to get it changed. In August 2005, with Lashkar-e-Taiba’s support, he traveled to the United States to begin the process of changing his name, using a lawyer in Philadelphia. In October he returned to Pakistan to work with Lashkar-e-Taiba.

Several months later, Pakistan’s tribal police arrested Headley near Landi Kotal in Khyber Agency, not far from the Afghanistan border, on his way to a meeting. The police were skeptical that he was Pakistani and believed he had disobeyed the posted signs saying that foreigners were not allowed in the tribal areas. After a few days of questioning, and after learning of Headley’s association with Lashkar-e-Taiba, the police transferred Headley to the Directorate for Inter-Services Intelligence.

“My name is Major Ali,” his ISI interrogator said. He asked what Headley was doing in the area.

“I was planning to go into India,” Headley explained, noting that he was working with Lashkar-e-Taiba and “had applied to change my name” in the United States.

Just as Zaki had done, Major Ali calculated that Headley could be a potentially useful asset. He asked for Headley’s cell phone number and inquired whether he would consider working for the ISI.

“I would not mind,” said Headley.29

ISI officials then apparently performed a background check on Headley, and an ISI operative who identified himself as Major Iqbal phoned a few days later and said he wanted to talk. They met in a safe house in Lahore early in 2006, and Major Iqbal fired off a series of questions. What Lashkar-e-Taiba courses had Headley taken? What assignments had Lashkar-e-Taiba wanted him to perform?

Headley again explained that Lashkar-e-Taiba had sent him through several training courses and wanted to use him as an operative in India. Major Iqbal approved and asked Headley to contact him when he returned from the United States. Headley agreed. In February 2006 his name was formally changed to David Coleman Headley. He returned to Pakistan a few months later.30

At their first meeting following Headley’s return, Major Iqbal explained that he wanted Headley to conduct intelligence work for the ISI in India. Headley agreed. He was an inexperienced operative, and Major Iqbal was skeptical about the training he had received from Lashkar-e-Taiba. “It wasn’t very good,” Major Iqbal later remarked.31

He instructed Headley to open an office in India using an immigration company as a front. Headley responded that he had a childhood friend, Tahawwur Rana, who worked in an office in Chicago for First World Immigration Services and could potentially be leveraged.

It sounded like a good idea, Major Iqbal said. “Acting as an immigration consultant,” he noted, would “help the work” that he wanted Headley to perform.32

Headley set up an office in Mumbai and the ISI chipped in $25,000.33 On his application for a business visa in India, which the Indian government approved, his Chicago-based friend Rana helped craft a formal letter explaining that “Mr. David C. Headley is our regional manager supervising and coordinating our operations in the Asian region and will be officially representing us there.”34 Headley now had a verifiable cover. He began taking ISI training courses in spotting and assessing potential recruits, recognizing Indian military insignia and movements, performing covert dead drops and pickups, and taking clandestine photography.35 He kept in regular contact with Lashkar-e-Taiba officials but was primarily operating for ISI.

The Mumbai Attacks

In September 2006, Headley set up his office in the southern part of Mumbai, a thirty-minute car ride from most of his clandestine surveillance targets. More than twenty million people make their home in Mumbai, India’s financial and entertainment hub. Headley conducted video surveillance of multiple sites, most notably the Taj Mahal Palace.36 A gaudy five-star hotel situated on the Mumbai harbor, the Taj was a landmark of Indian prestige and consequently a target for Lashkar-e-Taiba.

In December 2006, Headley returned to Pakistan and met with both ISI and Lashkar-e-Taiba officials.37 He briefed his ISI handler, Major Iqbal, on the contacts he had made in India and, most important, provided copies of his video surveillance. He did the same with his Lashkar-e-Taiba handlers. ISI and Lashkar-e-Taiba appeared to be in close collaboration on a plot to conduct terrorist attacks in Mumbai. Headley met with his ISI handler alone, the Lashkar-e-Taiba officials alone, and both together. He quickly realized, however, that the plot’s “instruction emanated from Major Iqbal” of the ISI, who closely monitored what Headley was doing and provided general guidance. Many of the tactical details, however, were left to Lashkar-e-Taiba to work out.38 This arrangement ensured that Lashkar-e-Taiba actually executed the operation, giving the ISI plausible deniability once the attack occurred.

Headley received instructions from ISI to return to Mumbai, which he did in February 2007.39 Major Iqbal had asked him to take additional video footage of the second-floor meeting areas of the Taj hotel, where defense contractors held conferences, as well as other potential targets.

Headley returned to Pakistan in May and provided the additional video footage to his handlers. As the plans developed, Major Iqbal instructed him to return to India in the summer to “carry out further surveillance of the Taj hotel” and to “get the schedules for the conference halls at that hotel.”40 Headley arrived in Mumbai around September but returned to Pakistan later that month. He provided the ISI with additional videos of target sites. By then the attack plan had begun to firm up. It would involve nearly a dozen Lashkar-e-Taiba operatives, who would storm several locations in Mumbai, take and kill hostages, and, it was hoped, upset the entire country. Lashkar-e-Taiba officials may also have hoped that the attack would exacerbate frictions between India’s Hindu and Muslim communities, perhaps even provoking an Indian military response, which would divide the country and facilitate Lashkar-e-Taiba recruitment.

But there were still questions about the operation. In March 2008, for example, Headley participated in a discussion of the attack with Lashkar-e-Taiba and Pakistani government officials in the city of Muzaffarabad, located in Pakistan-controlled Kashmir and barely 15 miles from the disputed border with India. The group carefully examined sea charts and debated possible entry points for the attack team, since most had agreed that the Lashkar-e-Taiba operatives would travel from Pakistan to India by sea. They went back and forth.

Zaki, an operational commander for Lashkar-e-Taiba, argued that the team should “land in front of the Gateway of India.” Located on the waterfront in south Mumbai, the stately Gateway of India is a basalt arch that towers 85 feet high over the harbor and was used as a landing place for British governors and other distinguished individuals arriving in Mumbai by boat.

Headley disagreed. He had seen armed coast guard boats there and contended that it would be too dangerous to land. “To get to that point,” Headley said, “the boat would have to circle around the southernmost point, which was a naval facility, naval base there, and it would be unsafe for a small boat to take that turn coming into the Gateway of India.”

A Pakistani navy official agreed with Headley.

Someone suggested that the operatives land 40 miles away and covertly make their way to Mumbai, but a senior Lashkar-e-Taiba official dismissed this option. “These boys would not be very sophisticated,” he explained, referring to the operatives, “and it would be hard for them to visit a country—a foreign location and then try to get a taxi or some kind of transportation back for such a long distance.”41

Unable to resolve the disagreement, ISI and Lashkar-e-Taiba officials ordered Headley back to Mumbai to examine potential landing sites. They also asked him to take more video footage of the Chhatrapati Shivaji Terminus (the main railway station), several bus stations, and the Taj hotel. So Headley returned to Mumbai in April 2008 and took several boat rides around the city, scouting different landing sites. He saved the locations in a Global Positioning System device that Lashkar-e-Taiba officials had provided him. He also took video footage of a site populated by fishermen on the west side of Mumbai, which Lashkar-e-Taiba ultimately decided would be the landing site. He took surveillance of the Nuclear Research Center in Mumbai and more footage of the Taj hotel, the railway station, and other sites.42

Later in April, Headley returned to Pakistan, where he briefed his ISI and Lashkar-e-Taiba handlers. He then returned to the United States, staying in New York and Philadelphia. On April 23 he sent an e-mail to Major Iqbal. “I have some preliminary information and I am forwarding it to you,” he wrote. “As I get more info, I will send it to you.”43 Major Iqbal had asked him to investigate several commercially available espionage devices, such as a wireless spy camera pen and a tiny, real-time digital camcorder, while he was in the United States.44

In June, Headley went back to Pakistan to meet with ISI and Lashkar-e-Taiba officials. ISI asked him to add at least one target, the Chabad House in Mumbai, to his list of surveillance targets. Chabad Houses exist in major cities around the world and serve as Jewish community centers, providing education and outreach for local Jews. But Pakistani officials believed that they had a more clandestine purpose. “That was a front office of Mossad,” explained Major Iqbal, referring to Israel’s external spy agency.

Headley nodded.

“Check the landing sites again,” Major Iqbal continued, as well as the target list that he would eventually be given.45

Headley understood Major Iqbal to mean that Lashkar-e-Taiba officials would give him a list of targets that were being finalized. Indeed, Lashkar-e-Taiba shortly provided him with an updated list of targets for surveillance—the Taj hotel, Chabad House, Maharashtra State Police headquarters, Naval Air Station, central train station, and several other sites—and wanted him to recheck the landing site. Headley went back to Major Iqbal before heading to India.

“Do a detailed surveillance,” Major Iqbal said.46 He then instructed Headley to shut down the office since Headley wouldn’t be able to return to India after the attack.

Meanwhile, Lashkar-e-Taiba was training a dozen operatives at a facility outside Muzaffarabad, though only ten would be deployed for the actual operation. By this time Lashkar-e-Taiba had decided that the attackers would travel to Mumbai by sea and use the fishermen’s landing site recommended by Headley. They would also fight to the death rather than attempt to escape following the attacks. The plan called for them to utilize a GPS device to facilitate coordination of the attack and remain in phone contact with other Lashkar-e-Taiba members during the operation.47

Headley returned to Mumbai one last time in July 2008. He took his final video footage of target sites, including the Chabad House, and added two potential locations that weren’t on the list—the Oberoi Hotel, which was near the landing point, and the Leopold Café, around the corner from the Taj hotel. He then returned to Pakistan, around August, and waited.

On November 26, Headley received a text message from Sajid. “Turn on the television,” Sajid had typed.48

Headley was mesmerized by what he saw. His careful, patient reconnaissance had paid off. Ten operatives trained by Lashkar-e-Taiba were now carrying out assaults at the sites he had videotaped, with firearms, grenades, and improvised explosive devices. Al Qa’ida–affiliated websites were swamped with messages from revelers celebrating the Mumbai attacks as a battlefield victory against India, which they viewed as an infidel Hindu state that oppressed Muslims.

Figure 16: Map of 2008 Mumbai Terrorist Attacks

To perpetrate the Mumbai attacks, Headley had worked with Lashkar-e-Taiba and Pakistan’s spy agency. Soon he would soon make his talents available to al Qa’ida leaders.

The Mickey Mouse Project

In November 2008, the same month as the Mumbai attacks, Lashkar-e-Taiba members discussed a new operation with Headley: targeting the Morgenavisen Jyllands-Posten. Headley cryptically hinted at his intention in a 2008 posting on an on-line forum called “abdalians7479,” which mostly included friends from Headley’s high school in Pakistan, Cadet College Hasan Abdal.49

“Everything is not a joke,” he wrote in the exchange, which was monitored by U.S. intelligence agencies. “We are not rehearsing a skit on Saturday Night Live. Call me old-fashioned but I feel disposed towards violence for the offending parties, be they cartoonists from Denmark or Sherry Jones (Author of Jewel of Medina) or Irshad Manji (Liberal Muslim trying to make Lesbianism acceptable in Islam, amongst other things). They never started debates with folks who slandered our Prophet, they took violent action,” he said, referring to the early followers of Muhammad.50

Lashkar-e-Taiba members gave Headley a thumb drive with basic economic and other information about Denmark, as well as photographs of two individuals they were interested in assassinating. One was Kurt Westergaard, the flamboyant Danish cartoonist who had drawn the cartoon of the Prophet Muhammad with a bomb in his turban. The other was Flemming Rose, the cultural editor of the newspaper, who was partly responsible for publishing the cartoons. Headley also met with an al Qa’ida sympathizer, Abdur Rehman, a retired major in the Pakistan Army whom he referred to as Pasha. Headley had met Pasha in a Lashkar-e-Taiba mosque in Lahore in 2003 and kept in regular contact. Pasha said that he approved of what Headley was doing, but urged him not to have lofty expectations.

“Lashkar guys had a habit of making plans and then backing off all the time,” Pasha said. “But if they did” decide not to move forward, he continued, he “knew somebody who would—who would take care of this.” That person, he hinted ominously, was “in the tribal area” and “had connections with al Qa’ida.”51

Pasha later divulged that his colleague was in regular contact with Shaykh Sa’id al-Masri, al Qa’ida’s general manager. Shaykh Sa’id was born in Egypt in December 1955 and had an impressive jihadist résumé. He was involved in the 1981 assassination of Egyptian president Anwar al-Sadat, spent three years in prison for his involvement, and left for Afghanistan in 1988 to join fellow jihadists. He apparently accompanied bin Laden from Afghanistan to Sudan in 1991 and served as the accountant for bin Laden’s Sudan-based businesses, including his company Wadi al-Aqiq.52 Shaykh Sa’id wasn’t just “connected” to al Qa’ida; he was at its very heart.

In early December 2008, Headley returned to Chicago to make final preparations for his surveillance trip to Denmark. He chose the cover name Mickey Mouse Project, because the popular Disney icon was a cartoon character, an easy way to remember that the terrorist operation’s goal was to attack the newspaper responsible for publishing the cartoons of the Prophet. He saved notes on his e-mail account so that he didn’t have to take them on the airplane, just in case he was stopped by U.S. law enforcement officials.53

Around this time the FBI began to notice Headley. Its agents now had intelligence suggesting that he might have been involved in the Mumbai attack, based in part on their cooperation with Indian intelligence. FBI agents visited the house of one of his cousins in Philadelphia and asked him a series of questions. The cousin said that Headley was in Pakistan.54 Headley’s second wife had contacted U.S. officials in Pakistan and said that she suspected Headley was involved in terrorism.55 FBI officials were concerned enough to continue monitoring his calls, e-mails, and movements. But they still struggled to grasp the extent of his operations.

In December 2008, Pasha sent an e-mail to Headley that was intercepted by U.S. intelligence agencies, commenting that al Qa’ida was still interested in supporting the Denmark attack. “First u visit MMP,” Pasha said, a reference to the Mickey Mouse Project in Denmark, and then “we will discuss and c the concerned person if needed.”56

Headley understood that the “other person” was Ilyas Kashmiri. Born in 1964, Kashmiri was a veteran of the anti-Soviet war in Afghanistan, during which he had lost an eye and an index finger. He eventually became the leader of Harakat ul-Jihad al-Islami and established his own unit, known as the 313 Brigade. “At that time,” wrote a colleague of Kashmiri, “he was the apple of the eye of the Pakistani establishment and he was running a big jihadi camp in the area of Kotli, Azad Kashmir.”57 Kashmiri spent most of his career running training camps and conducting operations against India. Around 2005, however, he apparently swore bayat to Osama bin Laden, relocated to Pakistan’s Federally Administered Tribal Areas, and leveraged his close relationship with al Qa’ida leaders such as Shaykh Sa’id al-Masri.58 Kashmiri hated India and the United States and was a deadly operator. He had been involved in dozens of terrorist attacks and plots across South Asia and Europe. He later became a senior al Qa’ida external operations official, and he sat on al Qa’ida’s military shura council until he was killed by a CIA drone in June 2011.

While Headley was impressed with Kashmiri’s accomplishments, he poked fun at the al Qa’ida operator’s lisp—Kashmiri had a habit of saying shishtem when he tried to say system.59

Pasha again reminded Headley that “if your friends decline”—a reference to Lashkar-e-Taiba—“we’ll do that.”60

In a subsequent e-mail, Headley asked Pasha how long he should conduct surveillance in Copenhagen: “How much time should i spend there? a week, 10 days or 2 weeks?”61

Pasha responded the next day: “i think a week or tens [sic] days r ok initially.”62

From the FBI’s and CIA’s perspective, Headley was involved in a startlingly complex range of clandestine activities. He was participating in terrorist plotting with al Qa’ida supporters, he remained in contact with Lashkar-e-Taiba operatives, and he was still nominally in touch with the ISI. He was his own boss, a free agent, which frustrated many of the people he worked with. “Futile are my advices,” said one of his Lashkar-e-Taiba handlers in an e-mail, “coz you do what you feel like.”63

In January 2009, Headley landed in Frankfurt, Germany, and drove to Copenhagen to conduct surveillance of Morgenavisen Jyllands-Posten. “It had five or six floors, and it was on King’s Square,” he jotted down.64 He tried walking into the building, but the front door was secured. As cover for his visit, he told newspaper executives that he was visiting on behalf of an immigration business that was considering opening up offices in Denmark and that he was interested in advertising the business in the Morgenavisen Jyllands-Posten.65 It was sufficient cover to fool newspaper representatives. He made an appointment with someone from the advertising office and conducted initial surveillance on his way into and out of the meeting. Headley then traveled to the Morgenavisen Jyllands-Posten’s office in Aarhus, Denmark’s largest port city, to conduct surveillance, making an appointment with a woman from the advertising department.

“I checked out business opportunities here,” Headley wrote to his friend Tahawwur Rana in Chicago, using coded language. “They seem quite promising. I am going right now to see if I can put an ad for our company and also check the feasibility to open up an office here.”66

Later that month, Headley traveled to Pakistan to discuss the plot with both Lashkar-e-Taiba and al Qa’ida supporters. The FBI and other U.S. agencies continued to track his movements. Records of his e-mail use show that between late January and early March 2009, he sent e-mail messages from various locations in Pakistan.67 He gave Pasha a copy of the surveillance video from the trip, which Pasha watched with interest.68 Pasha affirmed his willingness to help with the attack and explained that Lashkar-e-Taiba was unlikely to support it “because of the—the situation after the Mumbai attacks. People were getting arrested,” Pasha explained, “and there was tension generally for—for all these guys in Lashkar.”

Following the international uproar over the Mumbai attacks, Pakistani government officials began nominally to crack down on Lashkar-e-Taiba members, arresting a number of them. But the actions were generally for show; most were released shortly thereafter.

Pasha also had some broader advice. Lashkar-e-Taiba, he explained, was fighting “the ISI’s jihad.” But Headley should join Ilyas Kashmiri and his group because they were fighting “God’s jihad.”69

On to Waziristan

So Pasha asked Headley to take a trip to Waziristan to visit Kashmiri. Headley agreed. Around February 2009, Pasha, Headley, and two others traveled to Waziristan to talk to Kashmiri. It was a major turning point for Headley: he was now visiting one of al Qa’ida’s senior military officials.70

Headley explained to Kashmiri that he had conducted surveillance in Denmark for a terrorist attack against Morgenavisen Jyllands-Posten.

Kashmiri smiled and said that it was “very important that this—this attack be carried out as soon as possible.” Like many Muslims worldwide, he was still livid about the cartoons, which he considered “disgraceful and humiliating.” From a terrorist’s perspective, no one had punished the newspaper in the four years that had passed.

Kashmiri said that he had seen Headley’s video footage but had some suggestions on executing the attack. “Drive a truck of explosives inside—inside of that building,” he advised.

But Headley politely disagreed, saying that it was “not feasible,” since there were “blocks on the road that would not permit that.”

Kashmiri then offered more specific help. He knew several terrorists in England who might help in the attack, and suggested that Headley talk to them. He also asked Headley to return to India to conduct additional surveillance of several Chabad Houses there, as well as the National Defence College. “If we were able to conduct an attack on it,” said Kashmiri, “we would be able to kill more brigadiers in the Indian Army than had been killed in the four wars that Pakistan and India had fought previously.”71

Kashmiri provided Headley with 80,000 Pakistan rupees in cash—approximately U.S. $1,000—for tickets and travel expenses.72 In March, Headley went to India and conducted video surveillance in several cities, including Delhi, Pushkar, and Goa. In late March he returned to Pakistan and met with Lashkar-e-Taiba leaders, who informed him that the Denmark plot was “indefinitely postponed.”73 The ISI was also under enormous pressure after the Mumbai attack.

“Remove any stuff” from your house, Major Iqbal warned him, “pertaining to Lashkar and maybe move away for a little while.”74 Major Iqbal also ordered Headley not to contact him for the foreseeable future.

Undeterred, Headley arranged a meeting two months later with Ilyas Kashmiri in the tribal areas of Pakistan. Kashmiri explained that he had “spoken to the people that would carry out the operation from England” and had given them money for operational expenses. He also remarked that he wanted the assault to be a “stronghold option,” much like the Mumbai attacks. It would probably involve several operatives armed with grenades and machine guns, who would storm into the Morgenavisen Jyllands-Posten office to kill some employees and take others hostage. Kashmiri wanted to punish the paper and send an unambiguous message to anyone who might think about desecrating the Prophet Muhammad.

Kashmiri knew that pulling off a terrorist attack in Denmark would be strikingly different from committing one in India. “The Danish response forces would not be as incompetent and timid as the Indians, and, therefore, we should expect that the siege won’t last very long,” he reflected. “The attackers should throw out the heads of the hostages from the window . . . to rush the Danes into assaulting the building. Shoot them first,” he argued, “and then behead them later, so there wouldn’t be a struggle.” Kashmiri also advised Headley to “make a video of the attackers prior to the attack with some kind of message.”75

In July, Headley traveled to England to meet with the two men identified by Kashmiri and inform them about the Denmark plot. “He expected [you] to give us the manpower and the funds, as well as the weapons for that project,” said Headley.76 But their response was lukewarm. According to Kashmiri, they were supposed to provide £10,000 (about U.S. $16,000), but they gave Headley only £2,000 (about $3,000). The men also said that they couldn’t provide the manpower or the weapons, though they promised to travel to Pakistan and talk with Kashmiri. Still, Headley pushed on and traveled back to Copenhagen to conduct more surveillance. After pondering the logistical challenges, he made a phone call to Pasha, which was intercepted by U.S. intelligence.

Speaking in coded language, Headley noted, “If they are not fulfilling on it . . .” He paused. “Then B, B, they should, they should something as a B, option B.”

“Okay,” said Pasha.

Headley replied, “Yeah.”

“On the contrary, on the contrary,” Pasha interjected, “not B, but there should be B and C as well.”

“Yeah,” Headley responded, “there should be B and C as well.”77

As Headley later explained, he was suggesting that in addition to the stronghold strategy advocated by Kashmiri, which they referred to as Option A, they should have alternatives, what they called Options B and C. These might include assassinating Kurt Westergaard or Fleming Rose, or perhaps both of them.78

After leaving Copenhagen, Headley flew to Atlanta around August 2009. The FBI had put out a warning on him, and customs officers stopped him at Atlanta International Airport and asked him to explain the purpose of his travel to Copenhagen. Headley replied that he had been there as a consultant for his immigration business. They eventually let him go, and he went on to Chicago.79

On September 21, Headley and Pasha talked on the phone, which again was bugged by U.S. intelligence agencies. Based on press reports he had seen, Headley believed that Kashmiri had been assassinated. But Pasha said the reports weren’t true. “Buddy,” said Pasha, “the reports that are coming in . . . by the grace of God, he is doing well.”

“God willing,” said Headley, referring to Kashmiri, “uh . . . who—you mean the Doctor?”

“Yes, yes,” said Pasha.

“If this is true, I will say 100 prayers, 100 prayers. And also keep the fast, because—”

Pasha cut him off. “I don’t know,” he said, “but the matter over there has [sic] complicated. It is confirmed. Yesterday I had two . . . I received two confirmations yesterday that he is all right.”80

On October 3 the Denmark plot was back on. In fact, Pasha told Headley that Kashmiri was asking about him.81 Based on intercepted conversations with family members and other third parties, FBI officials thought that Headley intended to travel to Pakistan early that month. Before doing so, he planned to go to Philadelphia. On September 8 he had received an e-mail confirmation from Orbitz, an online travel agency, reflecting the purchase of a plane ticket from Chicago to Philadelphia on October 3. His plan was to meet with Pasha, Lashkar-e-Taiba officials, and Kashmiri in Pakistan and then to execute the Copenhagen attack.82

But the planning had gone far enough for U.S. government officials. Headley was arrested by FBI agents as he prepared to board the flight from Chicago to Philadelphia.

Business Must Go On

In characteristic fashion, Headley volunteered to work for the U.S. government after he was captured, telling FBI agents that he would implant a chip in or near Ilyas Kashmiri so that a CIA drone could target the al Qa’ida operative.83 It was a predictable tactic. Headley was willing to continue playing for all sides. At one point, after being erroneously informed that Ilyas Kashmiri was dead, he told a family member that “the main thing is the business must go on.” He wasn’t particular about which “company” he worked for, he continued, as long as he was involved in the game.84 This time, however, Headley’s game was over. The FBI had won, and it wasn’t about to let him go.

For FBI officials like Art Cummings, Headley came from a very different mold than Najibullah Zazi, Umar Farouk Abdulmutallab, and most other terrorists since September 11. He was unwilling to blow himself up on a subway, let alone conduct a terrorist attack. Rather, he preferred to remain in the shadows, collecting intelligence for various terrorist organizations and governments, including al Qa’ida. Headley was much more sophisticated than his predecessors. He used several methods of communication, including in-person meetings, telephone conversations, and e-mails from several accounts to throw off intelligence agencies. The account for one of his cell phones was registered to a dead man. So was his apartment in Chicago. And he relied on coded language in virtually all of his conversations. He referred to his Copenhagen plot as the “Mickey Mouse Project,” “mmp,” and “the northern project.” Instead of terrorism, he discussed “investments,” “projects,” “business,” and “action.”

In the end, though, Headley wasn’t as good as he thought he was. Despite his best efforts, FBI and U.S. intelligence agencies tracked his movements, listened to his phone calls, monitored his e-mail accounts, and collected intelligence from many human sources on his activities.

His uncle, William, was stoic about his fate. “If he is absolutely guilty,” he concluded, “then whatever punishment is doled out to him, he has to accept that.”85

If Headley symbolized a more diffuse and decentralized al Qa’ida that could reach out to individuals from allied organizations such as Lashkar-e-Taiba, then the third wave was about to get even more intriguing. This time, however, the threat did not come from Lashkar-e-Taiba or even al Qa’ida’s affiliate in Yemen. Instead it came from another group in Pakistan with ties to al Qa’ida: the Tehreek-e Taliban Pakistan.