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The American Behind India’s 9/11—And How U.S. Botched Chances to Stop Him

A senior European counterterror official who has investigated Headley in recent years thinks the American became an intelligence operative focused on terrorism.

“I don’t feel we got the whole story about Headley as an informant from the Americans,” the official said. “I think he was a drug informant and also some other kind of an informant.”

The transition from registered law enforcement source to secret counterterrorism operative would help explain the contradictory versions. But the duration and nature of intelligence work by Headley, if it was done, remain unknown.

Federal prosecutors and investigators declined to be interviewed on the record for this story. Pakistani officials, who also refused to be interviewed, have said they have cracked down on Lashkar and have denied that the ISI was involved in the Mumbai attacks.

Nonetheless, ProPublica and FRONTLINE talked to U.S. and foreign counterterror officials and other well-informed sources while reporting in the United States, India, Pakistan and Europe. A number of those officials and sources requested anonymity for their security or because they were not authorized to speak publicly about the sensitive case.

Headley was a wildly elusive figure who juggled allegiances with militant groups and security agencies, manipulating and betraying wives, friends and allies. He played a crucial role in an attack that had resounding international repercussions. And his unprecedented confessions opened a door into the secret world of terrorism and counterterrorism in South Asia — and closer to home.

Chapter 1: “The Prince”

David Coleman Headley is not his original name.

The 51-year-old was born Daood Gilani in Washington, D.C. His father, Syed Saleem Gilani, was a renowned Pakistani broadcaster. His mother, Serrill Headley, was a free spirit from a wealthy Philadelphia family. They moved to Pakistan when he was a baby, but the parents divorced and Serrill returned alone.

Headley grew up in an environment of Pakistani nationalism and Islamic conservatism. During a war with India in 1971, a stray bomb hit his elementary school in Karachi, killing two people. The incident stoked his hatred of India, according to his later accounts.

Headley attended the Hasan Abdal Cadet College, where he met his friend Tahawwur Rana. During testimony at Rana’s trial this year in Chicago, Headley said he was proud of studying at the elite military school, though he did not graduate. He described Rana as a “very good” student and himself as “very bad.”

Rana’s wife recalled an anecdote about Headley’s approach to morning prayers.

“Dave, he knocks on all the doors of students and he says, ‘Get up, get up, it’s time for prayer,’ ” Samraz Rana said in an interview. “And then when everybody gets up, he went to his room and went to sleep, you know. So he was laughing, he was like that.”

Headley clashed with his Pakistani stepmother. At 17, he returned Philadelphia to live with his mother. She owned the Khyber Pass, a trendy club that featured tarot readings and jazz and folk music. Her son helped manage the bar. He was tall and smooth and had a striking characteristic: One eye was brown, the other blue.

Employees nicknamed him “The Prince.”

“I think he was in culture shock,” said Djuna Wojton, a friend of his mother. “He spoke like with almost a British accent. And he was very well-mannered and very proper and polite.”

Headley enrolled at Valley Forge Military Academy & College but did not last long there. He studied at a community college and slid into heroin addiction. His first encounter with the law happened during a visit to Pakistan when he was 24. He used his friend Rana, then a Pakistani army medical student, as an unwitting shield.

The two drove to the tribal areas, where Headley bought half a kilogram of heroin and smuggled it back to Lahore, according to the DEA and Headley’s testimony. He thought Rana’s military ID card would prevent a police search if they were stopped, according to his testimony.

Days later, police in Lahore arrested Headley for drug possession, according to his testimony and U.S. officials. He somehow beat the charges.

In 1988, police caught him at the Frankfurt, Germany, airport en route to Philadelphia with two kilos of heroin hidden in a suitcase. The DEA took over, and he made a deal on the spot. His partners in Philadelphia got eight and 10 years in prison. He got four years.

It would become a pattern, said former CIA officer Marc Sageman, a respected terrorism expert who was a consultant for Rana’s defense.