The American Behind The 2008 Attack On Mumbai

toggle caption David Guttenfelder/AP

American David Coleman Headley was one of the leading planners of the 2008 terrorist attacks in Mumbai, which killed 166 people over three days at two five-star hotels, a train station and a small Jewish community center.

Headley, the son of a Pakistani father and an American mother, had been chosen for the mission because he looked like a non-Muslim Westerner. He used those looks — and his U.S. passport — to plan logistics for several of the places attacked in Mumbai.

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Headley's role in the Mumbai attacks is the subject of a new Frontline documentary by ProPublica reporter Sebastian Rotella. A Perfect Terrorist — which airs on PBS on Nov. 22 — chronicles Headley's journey from the United States to Mumbai, and reveals what U.S. and Pakistani intelligence officials knew about him before and after his mission.

Before Headley became a terrorist, he was what Rotella calls "a walking mix of cultures." His mother was part of an elite family from Philadelphia; his father was a Pakistani. Soon after his birth in the United States, Headley and his parents moved to Pakistan. After his parents divorced, Headley's mother moved back to the U.S. Headley stayed in Pakistan with his father, who sent him to elite military schools. But after getting into some trouble, Headley was sent to live with his mother above her bar, the Khyber Pass Pub in Philadelphia.

Music and alcohol flowed at the Khyber. And Headley, who had been raised in a conservative Pakistani household, had trouble fitting in.

"It's kind of this collision with the West after this upbringing in Pakistan," says Rotella. "As a young man, he slides into drug addiction and drug trafficking.

Headley became a drug smuggler, then a Drug Enforcement Agency informant in exchange for a lighter sentence. The DEA used his fluency in English and Urdu to help raid Pakistani heroin rings along the East Coast.

"They even send him, at one point, to do undercover work in Pakistan itself," Rotella tells Fresh Air's Terry Gross. "That kind of launches him into this crescendo of activities in the late '90s — where he's working as a DEA informant but also radicalizing."

Headley, still on probation, hooked up with an Islamic militant group called the Lashkar-e-Taiba. He started taking unauthorized trips to Pakistan in 2000 and 2001.

"He joins this classic military group and starts showing all of the signs of radicalization while working for the DEA," says Rotella. "Then Sept. 11th happens, and that kind of propels him more rapidly into the world of terrorism."

After Sept. 11

The DEA was initially unaware that Headley was becoming radical in his beliefs. They recruited him to help with anti-terrorism activities in New York, says Rotella.

"Essentially his role for the DEA expands from anti-drug to anti-terrorism work," says Rotella.

A few months later, a hearing ended Headley's probation three years early.

"The details of that are incredibly murky and contradictory," says Rotella. "What his probation officer and a defense lawyer and others familiar with his case say is that the government sought to end his probation early so that he could go to Pakistan and continue his counterterrorism work there as an informant."

But when Headley returned to Pakistan and started training with Lashkar-e-Taiba, his goal wasn't to send information back to the United States.

"He's actually training for real," says Rotella. "He's learning everything from basic counterterrorism to surveillance to survival [skills]. He's becoming a holy warrior."

Headley continued to travel back and forth between the United States and Pakistan. During this time, several phone calls were made to the FBI about Headley's possible ties with terrorism, but Headley was never interviewed.

Rotella says he has talked to several people about how Headley was able to train with Islamic militants and meet with al-Qaida operatives — without ever drawing notice from American authorities.

"Very serious U.S. forces tell me that the reality is, in the real world, it's not as easy as you think beforehand to detect a terrorist," he says. "But the fact is, the guy gets away with it, and he puts together this incredible blueprint that's carried out in Mumbai. And most people think that if it hadn't been for the scouting he did, the Mumbai attacks could not have been pulled off the way they were because they were absolutely reliant on the surveillance and the reconnaissance and the planning he helped do."

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Planning The Mumbai Attacks

During this time, Headley made several trips to Mumbai to plan which sites the terrorists should attack.

"He's able to spend time in these luxury hotels and these places Westerners go and do reconnaissance that just wouldn't be possible for 95 percent of the otherwise very capable operatives that Lashkar has," says Rotella. "He's unique in this sense. ... [In the Taj] the gunmen know the place inside and out, even though they've never been anywhere near Mumbai, let alone a luxury hotel. That was all thanks to this preliminary work that Headley had done."

Headley was arrested in Chicago in 2009 and charged with planning terrorist attacks in India and in Denmark, where he was involved in a plot to attack a Danish newspaper that had published satirical political cartoons of the Prophet Muhammad. A year later, Headley pleaded guilty in a deal that let him avoid the death penalty, but obligated him to testify against a friend, Tahawwur Rana, who was also charged with helping to plot the attacks in Mumbai.

At Rana's trial, Headley gave specific evidence about the close alliance between the ISI, Pakistan's intelligence force, and the Lashkar terrorist group.

"[He described] how the training works, how the funding works, how the coordinated decision-making works, and how they set out to do this attack together," says Rotella. "He talks about names ... places ... communications ... He's a gold mine for showing how this double game in Pakistan ... is really played.

Headley described meeting with both ISI and Lashkar officials before the Mumbai operation. He also described meeting a Pakistani military official at Lashkar headquarters. The officer gave Lashkar advice on how to carry out a maritime attack.

"Because of his evidence, the U.S. attorney's office in Chicago indicted Major Iqbal, [a Pakistani intelligence official], which is the first time you have a serving Pakistani intelligence officer charged in the murder of Americans," says Rotella.

"It's had a really damaging [effect] on the U.S.-Pakistani relationship, and I think really helped change the way a lot of people in the U.S. government see their relationship with U.S. security forces," he says, "partially because three years have gone by, and except for a couple of token arrests, the masterminds [behind Mumbai] are free."