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Coffee with David Headley

Malcolm Gladwell says in the book “What the Dog Saw” that the then US National Security Expert Gregory Treverton had famously made a distinction between puzzles and mysteries. Osama bin Laden’s details  are a puzzle he had stated. The US is not able to find him because of  lack of enough information. The key to the puzzle will in all probability come from someone close to bin Laden, and until that source is found, bin laden will remain at large.

The CIA must have felt ecstatic when they latched on to a man called David Headley.

David Headley (Daood Saleem Gilani) born in Washington D.C on June 30th, 1960 was a weird mix of Eastern and Western cultures and made for a near-perfect agent. His mother was Serrill Headley, a socialite from Maryland, and his father was Syed Gilani, a radio broadcaster and diplomat from Lahore.

After his birth in the US, the family had relocated to Pakistan, where Headley was brought up as a Muslim and schooled at an exclusive military academy.

Then his parents divorced and his mother returned to the US to open a bar in Philadelphia, and he rejoined her 17 years later.

He made the most of his dual identities to smuggle half a kilogram of heroin from Pakistan’s tribal areas to New York, selling it through his small video store.

German customs officers caught him four years later at Frankfurt Airport, when Headley was on his way to Philadelphia, with about two kilograms of heroin. He simply informed on his co-conspirators to the Drug Enforcement Agency (DEA) and tried saving his skin.

While, his co-accomplices were jailed for between eight and ten years, he very intelligently maneuvered his way to become a paid DEA informer.

He then worked for the DEA and cleverly infiltrated Pakistan’s drug syndicates.

And finally he offered a deal, suggesting he infiltrate Islamist radicals, which was absolutely difficult for the  CIA to refuse.

Adrian Levy and Cathy Scott-Clark, investigative journalists  authors of “The Siege” now complete the entire picture.

They say Headley was indeed a Lashkar-e-Taiba (LeT) agent,  who scouted targets for the 26/11 terror attack. But the authors say that he was “never anyone’s client” and his game plan was only to “save himself by sacrificing others”.

“Headley is complex and knowing. According to his own mother, an adventuress from Maryland, David was a person whose selfishness was derived from his lack of sense of self,”

“He went to Pakistan to be with his father yet he yearned to be  with his mother,  and soon joined her in the US.”

He began buying drugs in Pakistan in the early 1980s and he did so by manipulating his best friend Rana, a school friend of his and who was then a doctor in the Pakistan army.

“Headley used Rana’s military credentials and truck, to get into the tribal territories of Pakistan on drug obtaining missions, hiding his illicit cache in the military vehicle without Rana’s knowledge.”

The drugs plan was busted in 1984,  and then he gave up the syndicate around him. This happened on two more occasions as well.

On each occasion he made a deal with the DEA (Drug Enforcement Administration) and hence by default with the US intelligence as well.

“In 1998 he got arrested for importing heroin. The US Embassies and Africa had been devastated by Al Qaeda which was announcing its arrival on the global terrorist stage.

Headley/Gilani made an irresistible offer to the CIA. The offer was  to penetrate the Islamist movements in Pakistan.

He got into Lashkar but not until 2006, and then slowly edged also towards Al Qaeda, and in particular Ilyas Kashmiri’s 313 Brigade in Waziristan.

This was clearly known to the US Intelligence Agencies that were monitoring his email and phones. They had known all along that a US passport holder was closer than anyone else to capturing  Osama bin Laden at a time when capturing him was their sole and  prime objective.

But the authors Adrian Levy and Cathy Scott-Clark maintain through out their investigative account that Headley was never any one organisation’s  client.

He simply betrayed everyone.

He betrayed the LeT, his three wives, who never got to know about each other and his friend and co-conspirator Rana.

Headley even confused the US intelligence and the ISI, the authors quip.

He was finally arrested at O’Hare International Airport in Chicago while on his way to Pakistan in October 2009.

Headley immediately went into bargain plea with the US authorities, under which he could not be extradited to a foreign nation.

A team from India consisting of India’s National Investigation Agency (NIA) went to question and  interrogate Headley in his Chicago jail in 2010 to complete the mysteries surrounding the 26/11 attacks in Mumbai.

After his arrest and guilty plea, Headley cooperated with U.S. and Indian authorities and gave a lot of vital information about his associates.

Finally on the 24th of January, 2013,  a US Federal Court  sentenced David Coleman Headley to 35 years in prison for his role in the Mumbai attacks.


  1. “The Siege: The Attack on the Taj” ~by Adrian Levy and Cathy Scott-Clark, published by

Penguin. 2013.

  1.  “What the Dog Saw” ~by Malcolm Gladwell, published by Penguin. 2009.
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