Bluffmaster, drug-dealer, lover, terrorist… 26/11 mastermind David Headley’s life is a deep maze of deceits


David Coleman Headley is synonymous with the ghastly terror attacks on Mumbai. The 4-day-long coordinated attacks that started on 26 November, 2008, are dubbed as “India’s 9/11”. Islamist militants took the city as hostage, as the entire country sat paralysed in horror.

David Coleman Headley, aka Daood Gilani, the mastermind behind the planned attacks, changed many roles, both personal and professional, before he entered Mumbai to scout spots for assault. It was a strange coincidence that this man shared his name with another terror master Dawood Ibrahim, who planned the mega-carnage in Mumbai in 1993.  Their angst was the same: to avenge the “atrocities” inflicted by India on the Muslims.

A young Headley

The American-Pakistani double agent of CIA and ISI didn’t have a straight way to terrorism. It’s true, his Pakistani lineage helped him turn up at the door of terrorist group Lashkar-e-Taiba (LeT), but it was his western looks, and nonchalant casual American charm that helped him slip out of American law.

Born to a Pakistani diplomat father and a socialite American mother, Daood grew up with his father in Pakistan. His Western mother couldn’t remain within the confines of a Muslim marriage in Pakistan, and walked out on her husband when David was a little child. The custodial rules of Pakistan made sure Daood remained with his mother.

Daood with his mother Sheryll Headley

As the little boy grew up under his step-mother, he knew he was different. His playmates would call him “gora”, because of his light skin colour and his heterochromatic eyes, a blue right eye and a dark brown left eye. It was as if nature too, didn’t spare him from the effects of an inter-racial cocktail.

By the time Daood was in his teenage, he became extremely rebellious, and his father Sayed Gilani, worried about his son. By the time Daood was 17, he moved to Philadelphia in 1977, to be with his American mother Sheryll Headley. He helped Sheryll run her pub Khyber Pass. Sheryll’s free life bothered Dawood; he was steeped in conservative Islamist traditions, and to see his mother hang out with her male friends, while he waited for her at home muddled his young mind.

Daood seen here with mother Sherryl Headley and his step-sister

Eventually, he embraced the American way of life, and moved along, getting into drugs. He quite often travelled to his paternal home in Pakistan, and smuggle back heroin to America. In 1988, when he was busted in Germany for carrying 2 kg heroin, and was handed over to the US Drug Enforcement Administration (DEA), he quickly bought his way by promising to tell on his partners in Philadelphia. The deal worked out, and he was given four years in prison instead of 10.

A decade later, in 1997, Daood was trapped in a sting operation by the DEA and he wriggled his way out of the prison in just 9 months by promising to tell on all the drug activities in Pakistan. Soon, the smooth-talking man was the favourite of many DEA officials.

Daood migrated to America to be with his biological mother when he was 17.

As a DEA informant, Daood helped in making transcripts from Pakistani telephone intercepts, and passed on other vital information from the Pakistani drug mafia. The DEA spoilt him like a lone offspring, because no matter what Daood’s tantrums were, he would provide accurate news.

The same year, Islamist terror group al Qaeda was making its presence felt in the US. The militant group bombed US embassies in Tanzania and Tanya, and as retaliation, America bombed al-Qaeda hideouts in Afghanistan. The American anti-terror squad sought assistance from Daood to infiltrate into terror outfits in his homeland Pakistan.

Daood (second from right) in a local football team in Pakistan

Daood started getting played at the hands of the very authorities whom he manipulated.  However, he kept his double game on. To show that he was settling down, Daood married Shazia Geelani in Pakistan around 1999, with whom he had two children. All this while, in his many travels between Pakistan and America, Daood got drawn into the dark side of terror, and got racialised by the terror propaganda in Pakistan. He was thrilled by the anti-India slogans of the LeT, and fantasised about becoming a militant.

In 2000, Daood tried to gain inroad into LeT, after meeting the Lashkar head Hafiz Saeed. But sensing trouble, and his mixed parentage, Daood’s request was declined. He came back to America, but his freewheeling ways didn’t change; he got involved with a Canadian girl Portia, who had no clue about his wife and two kids in Pakistan.

Daood became radicalised after he attended a training course of LeT. He has two children from his first marriage.

This was just the beginning of Daood’s attempt to liaison with LeT. America desperately wanted information about the growing Islamist terror, and in Daood, they found the right mix of dare and deceit to get their dirty job done.

More about it in my next article…



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