David Headley
Judge Harry Leinenweber of the federal court in Chicago told David Headley that he deserved to be executed. Then he sentenced him to 35 years in prison. Headley, born Dawood Sayed Gilani, was a Pakistani-American who gathered the surveillance that helped plan the 2008 Mumbai attacks. He later surveyed the offices of a Danish newspaper for a second plot. The judge said he was hopeful the sentence would keep Headley under lock and key for the rest of his natural life. Yet Headley had once worked as an informant for the United States Drug Enforcement Administration. He had crossed borders with a changed name and a heroin record behind him. How did one man move between Washington, Lahore, Mumbai and Copenhagen without being stopped? Who saw the warning signs, and why did so little come of them? And what did he finally tell the investigators who caught him?
David Coleman Headley was born Dawood Sayed Gilani on the 30th of June 1960 in Washington, D.C. His father, Sayed Salim Gilani, was a well-known Pakistani diplomat and broadcaster. His mother, Alice Serrill Headley, worked as a secretary at the Pakistani embassy and came from Bryn Mawr, Pennsylvania. He had a younger sister, Syedah, and a half-brother, Danyal. Danyal later became spokesman for Pakistani Prime Minister Yousaf Raza Gillani and served as Pakistan's press attaché in Beijing.
Shortly after the birth, the family left the United States and settled in Lahore. Headley stood out there, with light skin and eyes of two different colors. His mother could not adapt to Pakistani culture and returned to America. Under Pakistani custody rules, she had to leave her children with their father. After her divorce she married four more times and spent time in Southeast Asia and Afghanistan.
Headley grew up in a political environment of Pakistani nationalism and Islamic conservatism, both sharpened by tension with India. In 1971, during the Indo-Pakistani War, bombs hit his elementary school in Karachi and killed two people. He went on to attend Cadet College Hasan Abdal, an elite international military prep school for boys. There he befriended Tahawwur Hussain Rana.
In 1977, at the age of seventeen, Headley left Pakistan after a difficult relationship with his stepmother. He moved in with his mother in Philadelphia and helped her manage pubs, including the Khyber Pass Pub and the adjacent Miss Headley's Wine Bar. Employees nicknamed him "The Prince." He enrolled at Valley Forge Military Academy but dropped out after one semester. He later left the Community College of Philadelphia without a degree in the 1990s.
In 1985 he married a Pennsylvania State University student. They divorced two years later because of his ideological hostility. He eventually moved to New York City and opened a video rental business in Manhattan.
At twenty-four, Headley smuggled half a kilogram of heroin out of Pakistan's tribal areas. He used Rana, an army doctor he knew from military school, as an unwitting shield. Several days later, police in Lahore arrested Headley for drug possession, but he was released. His trips to Pakistan had put him among heroin users, and he started using the drug himself. He also became involved in Pakistani drug trafficking.
Headley kept using Rana for years. In the late 1990s, after Rana had emigrated to the United States, Headley used Rana's legitimate immigration consulting company in Chicago to move drugs.
In 1988, police in Frankfurt, West Germany, arrested Headley as he traveled from Pakistan to Philadelphia. They had found two kilos of heroin in a false bottom of his suitcase. The case passed to the Drug Enforcement Administration, and Headley quickly made a plea deal. He agreed to surrender his partners in Philadelphia in return for a lighter sentence. He received four years, while his two associates received eight and ten. At sentencing, the judge told him that he was still a young man with a chance to change. The judge added that "what you did, not only to yourself, but to perhaps thousands, hundreds of victims, heroin users in this country is a terrible thing."
Headley overcame his own addiction but stayed in the drug trade. In early 1997 the agency caught him and another man in a sting operation as he tried to bring heroin in from Pakistan. Headley immediately offered to serve as a confidential informant. In January 1998 the agency sent him to Pakistan to dispel his partners' suspicions about his earlier absence and to gather intelligence on heroin networks. According to the agency, his help led to five arrests and the seizure of 2½ kilos of heroin. The agency insists this 1998 trip was the only one it paid for.
There is ample evidence, however, that Headley abused his status. He allegedly tried to set up heroin dealers using jailhouse phone calls that agents did not monitor. A mentally impaired Pakistani immigrant named Ikram Haq was found to have been tricked by Headley into a drug deal. Haq was acquitted on grounds of entrapment. One anonymous former associate said of Headley: "The DEA agents liked him. He would brag about it. He was manipulating them. He said he had them in his pocket."
For his cooperation, Headley received far less than his co-defendant from the 1997 arrest. He got fifteen months in jail and five years of supervised release.
In November 1998, Headley arrived at the low-security Federal Correctional Institution at Fort Dix. There he became an increasingly devout Muslim. In July 1999, only months into his sentence, his attorney Howard Leader asked for a supervised early release so Headley could travel to Pakistan for an arranged marriage. Judge Carol Amon granted the unusual request. Headley married a woman named Shazia, and they had two children.
While visiting Lahore, Headley was introduced to Lashkar-e-Taiba, a terrorist organization. He made more trips to Pakistan without the knowledge of American authorities, immersing himself in the group's ideology. He befriended its spiritual leader, Hafiz Muhammad Saeed. He committed himself to the group's struggle against India, which was supported by the Directorate for Inter-Services Intelligence, known as the ISI.
At the same time, Headley resumed work as an informant in New York City. He took part in an undercover operation that reportedly led to the seizure of one kilo of heroin. Yet he was also raising money and recruiting new members for Lashkar-e-Taiba, a group that had sworn allegiance with Al-Qaeda. Headley later testified that he discussed his views on Kashmir, the focus of the group's attacks, with his handlers. The agency insists it never knew about his radicalization.
The day after the attacks of the 11th of September 2001, his handlers tasked him with gathering counter-intelligence on terrorists through his drug contacts. But a New York City bartender named Terry O'Donnell reported Headley to an FBI task force. Headley's ex-girlfriend had told O'Donnell that Headley praised the hijackers and "got off on watching the news over and over again." Two Defense Department agents questioned Headley with his handlers in the room. He denied the accusations and cited his agency work as proof of loyalty. He was cleared, and the agency wrote no report on the interrogation.
On the 16th of November 2001, six weeks after that questioning, Leader and Assistant U.S. Attorney Loan Hong asked Judge Amon to end Headley's supervised release three years early. She agreed. Leader has claimed the agency helped drive the request, so that Headley could keep gathering intelligence in Pakistan. The agency says Headley wanted it for family reasons. The agency also says it deactivated him as an informant on the 27th of March 2002. Headley says he stopped working for it in September 2002, and other agencies say he remained an operative as late as 2005.
In February 2002, Headley attended a three-week introductory course on Lashkar-e-Taiba ideology and jihad at a training camp. That summer, his mother, who had moved to Oxford, Pennsylvania, confided to friends that her son had become a religious fanatic. A friend of hers, Phyllis Keith, noticed Headley parking his car behind the house as if to hide it. Keith reported him to the FBI office in Philadelphia, which apparently did not follow through.
In August 2002, Headley returned to Pakistan for a second stint at the camp and spent his spare time with Shazia in Lahore. Despite that marriage, he had embarked on affairs in the United States. The month before, he had become engaged to a long-time Canadian girlfriend in New York City. When he landed in New York in December 2002, border inspectors looking for unusual travel to places like Pakistan briefly detained him. They found nothing amiss and released him. He married her at a Jamaican resort a few days later.
In the summer of 2005, she confronted him about his other marriages and his trips to the camps. Headley hit her during an argument at his Manhattan video store. After his arrest for assault, she called a government hotline and described his terrorist activities. The FBI's Joint Terrorism Task Force interviewed her three times. Citing his agency work, the FBI did not consider him a threat. The investigating agent speculated that she had "an axe to grind" over his other marriage. Headley was never questioned, the assault charge was dropped, and he later closed his video store.
In June 2006, she applied for a green card under the Violence Against Women Act. In her immigration interview she described his radicalization and terrorist training. She also spoke of his anti-Semitic and anti-Hindu prejudices and his praise for suicide bombers. Immigration officials granted the green card but alerted no law enforcement, because strict privacy laws cover immigration cases involving spousal abuse.
By 2005, Headley's training had advanced to the point where he wanted to fight in Kashmir. Instead, Lashkar-e-Taiba referred him to Sajid Mir, its foreign recruiter. Under Mir's direction, Headley went to Philadelphia and legally changed his name to David Coleman Headley, taking his mother's surname. Pennsylvania law requires a background check for name changes, but state officials apparently never uncovered his drug convictions. The new name would help him hide his Pakistani ancestry from Indian authorities, who impose strict entry requirements on people of Pakistani descent.
Indian investigators were later surprised at how easily Headley obtained an Indian visa from the consulate in Chicago. On his application he falsely stated that his father's name was William Headley and that his own name at birth was "Headley." That was hard to refute, because a U.S. passport does not list the father's name or require endorsements on name changes. Indian officials said that if the change had been noted, immigration officers would have been alerted during his many visits. During those visits he befriended several people, including Rahul Bhatt, who said he never suspected Headley of wrongdoing.
In January 2006, Headley established ties with Abdur Rehman Hashim "Pasha" Syed, a retired Pakistan Army major and militant. Syed put him in touch with Major Iqbal, a mysterious figure believed to have coordinated Lashkar-e-Taiba activity as an ISI officer. Under sworn testimony, Headley recalled meeting Iqbal and Iqbal's superior, a Pakistani colonel, in a safe house. Iqbal and Mir reportedly became his ISI handlers and oversaw his training in espionage techniques. He met them separately so the ISI could keep plausible deniability.
In February 2006, border inspectors at New York's John F. Kennedy International Airport detained Headley again after a trip from Pakistan. They released him again. That same month, he contacted his former handler at the drug agency for the final time.
Over the course of 2007, the plot for the Mumbai attacks started to take shape. The Western-looking Headley seemed the ideal militant for reconnaissance. Using $25,000 supplied by Iqbal, he opened a Mumbai branch of Rana's immigration business as a front company. Between 2007 and 2008, he made five trips to Mumbai to scout landmarks. He stayed at the Taj Palace Hotel, which Iqbal and Mir had identified as their main target. Using his ISI training, he shot hours of video during in-house tours.
Iqbal and Mir were emboldened by his intelligence and made the attack more ambitious. As the target list grew, Headley scouted the Oberoi Trident Hotel, the Leopold Cafe, and the Chhatrapati Shivaji Terminus. When the group chose Nariman House, a Jewish community center, he visited posing as a Jew. He also took boat tours to find where attackers could reach the city by water. He found a landing spot at a fishermen's slum in the Colaba area of southern Mumbai and gathered GPS coordinates. A frogman in the Pakistan Navy helped with the maritime reconnaissance.
In March 2009, he made another trip to India, this time to survey the National Defence College in Delhi and Chabad Houses in several Indian cities.
In October 2008, one month before the Mumbai attacks, Mir and Iqbal gave Headley a new assignment. They wanted him to scout the Danish newspaper Jyllands-Posten in Copenhagen, in retribution for its publication of cartoons of Muhammad. In January 2009, Headley visited its editorial offices and claimed to be interested in buying ad space. After meeting the paper's advertising executive, he drove to its building in Aarhus and met another executive.
Elsewhere on that trip, he filmed Copenhagen, including the newspaper's offices. He looked into leasing an apartment that an attack team could use. He also inquired about a job as a secretary.
Then his Lashkar-e-Taiba handlers told him the plot would be put on hold, and Headley grew disenchanted with the group. Syed became his new handler and introduced him to Ilyas Kashmiri, leader of Harkat-ul-Jihad al-Islami, an Islamist organization active in Pakistan, India and Bangladesh.
Headley planned to return to Copenhagen in the summer of 2009. Kashmiri put him in touch with two al-Qaeda operatives, Simon and Bash, who lived in Derby, England. On the 26th of July 2009, Headley visited Derby and learned that they did not want to take part in the Denmark plot and could not supply weapons. They offered him US$15,000 in financing instead. In Stockholm he met Farid, a veteran militant, who could not help because the Swedish Police Authority kept him under tight surveillance.
Headley arrived in Copenhagen by train on the 31st of July. He filmed a Royal Danish Army barracks and approached drug dealers about acquiring guns.
According to later accounts, Hafiz Muhammad Saeed, with help from Kashmiri, drafted Headley into the Danish plan. Headley's original handler, Mir, had wanted him to stay focused on the group's mission against India.
On the 5th of August 2009, airport inspectors questioned Headley as he arrived at Hartsfield-Jackson Atlanta International Airport. By then the FBI had put him on a watch list and begun a two-month surveillance operation. Agents debriefed his former handler and reviewed records of past inquiries. Eventually, investigators began to suspect him of involvement in the Mumbai attacks. On the 9th of October he was arrested at Chicago's O'Hare International Airport, trying to fly to Pakistan to deliver the footage he had collected in Denmark.
During interrogation, Headley gave up information on Lashkar-e-Taiba, Al-Qaeda, the ISI, and various plots and methods. Supervised by federal agents, he helped set a trap for a militant in Germany and tried to lure Mir out of Pakistan. He and Rana were charged over the Jyllands-Posten plot, including scouting its office and a nearby synagogue. The FBI later charged Headley with conspiring to bomb targets in the Mumbai attacks and providing material support to Lashkar-e-Taiba.
India's National Investigation Agency registered its own case against Headley and Rana. After questioning Headley in Chicago for a week, it asked a Delhi court for non-bailable warrants. Home Minister Palaniappan Chidambaram said American authorities had shared "significant information." Assistant Secretary of State Robert O. Blake, Jr. promised India "full access." But Headley's plea agreement with U.S. Attorney Patrick Fitzgerald appeared to rule out extradition. Chidambaram said India would keep trying.
In India, opposition parties demanded to know why Headley had been allowed to travel freely for years between India, Pakistan and the United States. Some analysts speculated that he was a double agent for the Central Intelligence Agency. Paul Gimigliano of the CIA's Office of Public Affairs replied: "Any suggestion that Headley was working for the CIA is complete and utter nonsense. It's flat-out false." Indian investigators also wanted the FBI to share its recordings of his calls with Pakistani handlers. They hoped to match them against voices taped on cell phones during the attacks. In April 2010, U.S. ambassador Timothy J. Roemer told reporters in New Delhi that Washington was working at the "highest level" to give India access.
In October 2010, news reports revealed that American authorities had known much more in advance. Headley's Moroccan wife had contacted them in 2007. She said she showed the U.S. embassy in Islamabad photographs of their stay at the Taj Mahal Palace Hotel in Mumbai. She warned them that he was doing something on behalf of Lashkar-e-Taiba. Some analysts speculated that the United States let Headley work undercover despite knowing of his terrorist ties.
In June 2010, National Security Adviser James Jones announced that India's National Investigation Agency had been given access to Headley. Its investigation concluded that Lashkar-e-Taiba carried out the Mumbai attack under the guidance of the ISI. Headley said the ISI was engaged with the Lashkar commanders at every stage of the plot. A classified Indian report said some of his scouting trips were financed and planned by the ISI. When it leaked to American media in October 2010, Pakistani authorities denied its conclusions. On the 31st of May 2011, Headley contradicted his earlier statements and testified that the ISI leadership was not involved in planning the attacks. He also claimed that Ishrat Jahan, thought to be a case of a staged police "encounter killing," was a trained Lashkar suicide bomber.
The 2010 blast at a German bakery in Pune injured at least 53 people and killed 18, six of them foreigners. Indian Home Secretary G. K. Pillai and the Hindustan Times linked Headley to it. The newspaper reported that he had visited Pune in July 2008 and March 2009. United States Director of National Intelligence James R. Clapper later reviewed the slip-ups in handling Headley, and his report went to India's Union Home Ministry.
On the 24th of January 2013, Judge Leinenweber handed down the sentence in the United States District Court for the Northern District of Illinois. Headley could have received life imprisonment. Federal prosecutors instead recommended 35 years because of his extensive cooperation. He had given details on how Lashkar-e-Taiba operated, and his information led to charges against Rana and six other terrorist figures.
The day after the sentence, India announced it would keep seeking Headley's extradition. In April 2013 it was reported that he had written a memoir in prison about his involvement with Lashkar-e-Taiba and the Mumbai attacks.
In July 2015, Mumbai police sought a deposition from Headley by video conference to build evidence against Zabiuddin Ansari. On the 10th of December 2015, a Mumbai court pardoned Headley and made him an approver in the case. His deposition began on the 8th of February 2016 before the Bombay High Court, via video link from his American prison cell. He told the court that the group had made two unsuccessful attempts before finally striking in November 2008, one in September and one in October.
On the 9th of February 2016, Headley reportedly confessed that Lashkar-e-Taiba and the ISI had penetrated the Indian Army to place spies. He said an attack had also been planned on Indian defence scientists due to meet in the conference hall at the Taj Hotel in 2007. For that purpose, he said, he had carried out reconnaissance on the naval air station INS Kunjali, on INS Shikra and on the Siddhivinayak Temple in Mumbai.
On the 24th of July 2018, it was reported that Headley had been seriously injured in an attack in prison. He was admitted to the critical care unit of Evanston Hospital.
His story has reached the screen. J. Brandon Hill portrays him in the 2015 Indian action thriller Phantom, and Carl Andrew Harte plays him in the 2025 Indian spy thriller Dhurandhar.
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Common questions
Who is David Headley?
David Coleman Headley, born Dawood Sayed Gilani on the 30th of June 1960 in Washington, D.C., is a Pakistani-American who conducted surveillance for the 2008 Mumbai attacks. He worked with the Pakistan-based group Lashkar-e-Taiba and earlier served as an informant for the U.S. Drug Enforcement Administration.
What did David Headley do in the 2008 Mumbai attacks?
David Headley made five trips to Mumbai between 2007 and 2008 to scout targets for Lashkar-e-Taiba. He filmed the Taj Palace Hotel, scouted the Oberoi Trident Hotel, the Leopold Cafe, the Chhatrapati Shivaji Terminus and Nariman House, and found a landing site in the Colaba area.
How was David Headley caught?
David Headley was arrested on the 9th of October 2009 at Chicago's O'Hare International Airport while trying to travel to Pakistan. The FBI had placed him on a watch list and run a two-month surveillance operation before the arrest.
What was David Headley's sentence?
On the 24th of January 2013, Judge Harry Leinenweber sentenced David Headley to 35 years in prison. Prosecutors recommended that term instead of life because of his extensive cooperation with the government.
Why did David Headley change his name?
David Headley legally changed his name from Dawood Sayed Gilani to David Coleman Headley in Philadelphia, taking his mother's surname. The change helped him hide his Pakistani ancestry from Indian authorities, who impose strict entry requirements on people of Pakistani descent.
Was David Headley an informant for the U.S. Drug Enforcement Administration?
Yes, David Headley became a confidential informant for the Drug Enforcement Administration after his 1997 arrest in a sting operation. The agency says his 1998 trip to Pakistan was the only one it paid for and that it deactivated him on the 27th of March 2002, though he and other agencies give later dates.
What was the David Headley plot against Jyllands-Posten?
David Headley scouted the Danish newspaper Jyllands-Posten in Copenhagen and Aarhus in January 2009 for an attack in retribution for its cartoons of Muhammad. The plot failed, and he was charged over it along with Tahawwur Hussain Rana.
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69 references cited across the entry
- 3NewsScout in Mumbai attacks was DEA informant while in terror camp, authorities saySebastian Rotella — October 17, 2010
- 4NewsDid the U.S. know more than it let on about Mumbai attacks suspect?Sebastian Rotella — November 22, 2011
- 6NewsIndian report accuses Pakistan's intelligence service of significant role in Mumbai siegeEmily Wax et al. — October 21, 2010
- 7NewsChicago man gets 35 years in Mumbai terror attackAnnie Sweeney — January 24, 2013
- 10NewsPak PM's PRO admits he is Headley's half-brotherSachin Parashar — November 29, 2009
- 11Alice Serrill Headley, born on her father's farm in Laurel, Maryland, July 29, 1939, was a daughter of L. Coleman Headley and his wife, the former Frances Ladd Kercher. She was educated at Catholic sc
- 13VideoWho is David Coleman Headley? The American behind India's 9/11 FRONTLINEFRONTLINE PBS Official — April 18, 2015
- 14NewsAn Accused Plotter With Feet in East and WestGinger Thompson — November 21, 2009
- 15Inquirer.com: Philadelphia local news, sports, jobs, cars, homesJanuary 1, 1970
- 17Inquirer.com: Philadelphia local news, sports, jobs, cars, homesJanuary 1, 1970
- 18NewsAlleged Terrorism Plotter David HeadleyDecember 9, 2009
- 19NewsWho was David Headley? Was he involved in the Mumbai shootings?Joseph Tanfani et al. — McClatchy Newspapers — December 14, 2009
- 20NewsA Terror Suspect With Feet in East and WestGinger Thompson — November 22, 2009
- 21NewsD.E.A. Deployed Mumbai Plotter Despite WarningGinger Thompson et al. — November 7, 2010
- 26The Making of a TerroristGerald Posner — December 8, 2009
- 27NewsThe American Behind India's 9/11—And How U.S. Botched Chances to Stop HimSebastian Rotella — ProPublica — January 24, 2013
- 28NewsBefore '08 Mumbai attacks, U.S. was warned key figure in plot had terror tiesSebastian Rotella — October 16, 2010
- 30A Perfect TerroristPBS
- 31NewsPakistani American posed as Jew to case Mumbai ChabadJewish Telegraphic Agency — November 15, 2009
- 33NewsBad company: Lashkar-e-Tayyiba and the growing ambition of Islamist militancy in PakistanLisa Curtis — The Heritage Foundation — March 11, 2010
- 34Ilyas Kashmiri survived last month's airstrike in PakistanBill Roggio — October 13, 2009
- 38NewsEx-Military Officer in Pakistan Is Linked to 2 Chicago Terrorism SuspectsDAVID JOHNSTON et al. — November 18, 2009
- 39NewsIn alleged terror plot, a troubling twistSebastian Rotella — October 31, 2009
- 40NewsTerror suspect likely to change pleaMarch 16, 2010
- 41NewsMumbai terror suspect pleads guiltyCNN — March 18, 2010
- 42NewsNIA seeks non-bailable warrant against Headley, Rana, SaeedPTI news wire — July 9, 2010
- 43NewsDavid Headley's Plea Agreement (PDF – 61.27 KB)International News section — March 19, 2010
- 44NewsIndia wants to question U.S. man on Mumbai attackNigam Prusty — March 19, 2010
- 45NewsHeadley hid Pakistani origin from Indian consulate in ChicagoDecember 26, 2009
- 46NewsSecurity expert discusses missed warnings on terrorist suspectAllison Roy — Medill Reports Chicago — November 11, 2010
- 47Exclusive: I had a hunch he was an agentJonathan Miller — January 21, 2010
- 48NewsHeadley may have tipped off US about 26/11- Politics/Nation-News-The Economic TimesDecember 16, 2009
- 49MagazineIndia seeks Headley probe tape from FBISoni Sangwan — December 20, 2009
- 50NewsAccess to Headley being worked out at the highest level: RoemerApril 19, 2010
- 51NewsU.S. Had Warnings on Plotter of Mumbai AttackJane Perlez et al. — October 16, 2010
- 52NewsDavid Headley: Truth & liesNDTV — March 17, 2010
- 53NewsHeadley Pleads Guilty Fueling Double Agent SpeculationJeremy Kahn — March 22, 2010
- 54India granted access to HeadleyJune 5, 2010
- 55News2008 Mumbai Attacks Plotter Says Pakistan's Spy Agency Played a Role8 February 2016
- 56NewsISI guided LeT at every step for 26/11Diwakar & Vishwa Mohan — June 10, 2010
- 57Ishrat Jahan was an LeT suicide bomber: Headley to NIANDTV — July 5, 2010
- 59NewsEight die in India's first big attack since MumbaiThomson Reuters — February 13, 2010
- 61NewsSlip-ups over Headley issue: U.S. sends review findings to IndiaVinay Kumar — November 8, 2010