David Coleman Headley: The Perfect Terrorist?

Headley, leaning.

Headley, leaning. (Family of David Headley. )

May 22, 2011

David Coleman Headley didn’t look like a terrorist.

The man tapped to scout targets for the November 2008 Mumbai terror attacks — a slaughter that left 166 people dead, including six Americans — Headley had the basics required by Lashkar-i-Taiba, the Islamic militant group he joined in 2002: the Pakistani nationalism; the dedication to jihad against the west.

But he also offered something his brothers in the cause couldn’t: a U.S. passport.

Born in Washington, D.C. to an American mother and Pakistani father, Headley looked like a non-Muslim Westerner. He called himself David Headley — not Daood Gilani, his given name. He was older, too — in his late 40s — and had connections to a Chicago-based company which he could use as a front while he did reconnaissance in India.

“This guy is perfect,” says Charles Faddis, a former CIA operations officer. “I mean he effectively can walk through every screen that the Indians have thrown up over their years of experience, every fence they’ve erected to keep out Lashkar operatives. Whether it’s his age, his background, his documentation, he’s just not going to be one of those guys that the Indians are focused on.”

Over the past six months FRONTLINE and ProPublica have joined forces to investigate Headley’s life, including his work as an informant for the U.S. Drug Enforcement Administration and his associations with Lashkar-i-Taiba and Pakistan’s powerful intelligence service, the ISI. Drawing on Sebastian Rotella’s extensive reporting, our investigation has brought Headley into sharp focus as a man of supreme confidence with convictions and loyalties that can shift in an instant. Terrorism experts marvel at his survival skills, how he carefully balances allegiance with betrayal.

A prime example of Headley’s finely honed sense of self-protection may be on display this week in a Chicago federal court, where he is expected to be the star witness against his high school friend and business partner, Tahawwur Rana. Rana is charged with three counts of giving material support to terrorists, one of whom is Headley himself.

Prosecutors allege that starting in 2006, Rana, a Canadian citizen who owned a business in Chicago providing U.S. worker visas to immigrants, allowed Headley to use that operation as a cover while casing Mumbai. Headley then used the same cover in Copenhagen, where he planned to attack Jyllands Posten, the newspaper famous for printing 12 caricatures of the Prophet Mohammed in 2005. Rana is pleading not guilty.

In an exclusive interview, Rana’s wife, Samraz denies that her husband was complicit in any terrorist activities, and suggests that David Headley hid behind different identities. The Headley she knew was “like a brother,” she says, adding he called her his sister. “In my family if you’re going to be my brother it’s the most respectable thing for any person. And that was very special for me. And that’s why I respected him a lot, you know.”

Now though, Mrs. Rana is faced with the reality that Headley has turned on her husband, his friend of more than 30 years. U.S. prosecutors say the evidence shows Tahawwur Rana knew about and participated in Headley’s terror plots. But Rana’s lawyer, Charles Swift, says the government is going after the wrong man. He says Headley, who has struck a plea deal with prosecutors to avoid the death penalty, should be the target. “They’re using a whale to catch a minnow,” he says.

The plots, the betrayal: for Mrs. Rana, it is almost too much to comprehend. Sitting in her home in Chicago, she wonders how David Headley, a professed devout Muslim, could do these things.

“We believe in the same, that if God has given you the life and God has given the life to an ant, if you are going to kill an ant we have been answerable to God.” She shifts in her seat, adjusting the scarf draping her head, collects her thoughts and continues: “If it is true that he has done [these things], that’s … the worst thing I can imagine. David Headley is insane. That’s it. I can say only this thing. No person with [a] brain can do these things. He [doesn’t] know what he is doing.”

Tom Jennings is producing a documentary on David Coleman Headley scheduled to air on FRONTLINE in the fall of 2011.

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