The Life & Crimes of a Jihadist from Philly

An Old City barkeep helped terrorists carry out the 2008 Mumbai attacks.

By Jonathan Valania
Add Comment Add Comment | Comments: 3 | Posted May. 18, 2010

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Photo by Alex Fine

On the afternoon of Nov. 26, 2008, death came ashore at the Indian coastal city of Mumbai in the form of 10 Pakistani assassins aboard a rubber dinghy. Young and cocky, the killers were dressed in bluejeans and cargo pants, pumped up on steroids and ripped from months of rigorous physical training. They brandished AK-47s and carried backpacks loaded with grenades and ammo. When fisherman asked them what was going on, the gunmen told them in fluent Marathi to, in effect, go fuck themselves. The fishermen reported the incident to police who, tragically, paid it no mind.

Over the course of the next 50 hours, the gunmen would kill 164 people—including six Americans—and injure hundreds in a vicious three-day wave of violence, according to the Department of Justice. They split up into small groups and fanned out across the city, navigating by GPS and keeping in constant cell phone contact with their minders back in Pakistan. They blew up taxis, tossed grenades into crowds, murdered police officers and indiscriminately mowed down bystanders at a crowded cafe, movie theater and a train station with a blizzard of hot lead. They stormed two five-star hotels, set them on fire, took hostages and slowly tortured, disfigured and then executed them one by one.

One team of gunmen entered a women and children’s hospital with the intent of killing as many patients as they could, only to be thwarted by hospital staff that had locked down certain wards. Once inside, the gunmen again asked the staff their religious affiliation. When one man answered ‘Hindu’, they shot him in the head. Another team took over a Jewish center called the Mumbai Chabad House, where they killed six hostages, including a rabbi and his pregnant wife. The gunmen injected cocaine, LSD and steroids to enable them to fight police for 50 hours straight without food or sleep. Nine of the 10 were eventually killed by police, with one taken alive.

This would become known as the Mumbai Terror Attacks around the world, but inside India it would be called 26/11, or India’s 9/11. The bloodbath would shock the world and push India and Pakistan, two nations with nuclear arsenals and a long history of violence, to the brink of war.

The trail of evidence led not only back to neighboring Pakistan but also halfway around the world to Philadelphia.

David Coleman Headley lived in Philly for more than 30 years before moving to Chicago shortly before the Mumbai attacks. Authorities allege that Headley served as advance man for many jihadist terror plots, and scouted out locations for the Mumbai attacks. He was arrested by federal agents back in October, and in late March he pleaded guilty to charges that he served as reconnaissance man for the Mumbai operation, traveling to India on five occasions to scope out and videotape the pre-ordained killing zones—chosen for their landmark status, sizable number of foreigners they attracted and relative lack of security—and record GPS coordinates, all of which he hand-delivered to the operation’s Pakistani masterminds.

Headley also pled guilty to being one of the ringleaders of a plot to attack the offices of Jyllands-Posten, the Denmark newspaper which drew the fury of the Islamic world in 2005 for publishing mocking cartoons of the Prophet Muhammad. Working in tandem with al Qaeda, Headley made numerous trips to Copenhagen to scope out and videotape the newspaper offices. The plot was simple: storm the newspaper, take everyone hostage, behead them one by one and throw their heads out into the street. It was designated a suicide mission and if all went according to plan there would be no survivors.  The plot was in its advanced stage, but authorities arrested Headley before it could become operational.

Headley struck a deal with authorities after his arrest. He would be spared the death penalty in exchange for complete cooperation. His information has reportedly led to numerous arrests in Pakistan, including former army officers, former intelligence operatives and members of Lashkar-e-Taiba, a militant Islamist organization based in Pakistan that routinely carries out paramilitary operations in the Kashmir region that buffers the borders of India and Pakistan. LET is said to have a cozy relationship with Pakistan's Inter-Services Intelligence (ISI),  the equivalent of the CIA. Additionally, Headley’s cooperation led to the arrest of an officer in the Indian army who was caught forwarding classified documents to the Pakistani army via computer, according to news reports.

Headley is an American citizen whose mixed parentage—his father was a Pakistani national and his mother was American—enabled him to straddle the divide of the secular West and the Islamic East, making him a high-value asset for any jihadist organization. Headley’s mother, Serrill Headley, founded Old City’s Khyber Pass (now just known as the Khyber) back in the ’70s. As a teenager, Headley lived above the bar and he would eventually manage it for his mother. He would later go on to become a video-store entrepreneur, international drug smuggler, and, after getting caught with two kilos of heroin, he bacame an informant for the DEA, according to the Inquirer. He would also earn the grim distinction of being the American jihadist with the highest body count. Much has been written about Headley, especially in India, where he is regarded as Public Enemy No. 1, but for all we have learned, he remains something of a cipher, quite literally an international man of mystery.

Headley was born Daood Gilani in 1960 in Washington, D.C. His mother, who died in 2008, grew up in Bryn Mawr and ran away from home when she was 15, eventually settling in the nation’s capital and finding work as a secretary, according to the Inquirer.

“She was very independent, very freewheeling,” says her brother, William Headley, who owns a day-care center in Nottingham, Pa.
It was in D.C. that Serrill met and eventually married Pakistani diplomat Syed Saleem Gilani.

“He was very charming and distinguished,” William says. “He swept her off her feet.”

Shortly after Daood was born, the family moved to Karachi, Pakistan. But Serrill, whom her brother characterizes as a proto-feminist, soon chafed under the chauvinism of Pakistani society.

“She told me that Daood’s father had hit her,” says Lisa Sloat, a veteran bartender in the Philadelphia restaurant scene who interviewed Serrill for a bar guide she used to publish in the early ’90s. “She told me she left him and escaped through the Khyber Pass to Afghanistan. That’s why she named the bar Khyber Pass.”

Serrill eventually returned to Philadelphia—without Daood (“In Pakistan, men own the children,” she was quoted as saying at the time. “There are no rights for women.”)—and in 1973 she enrolled in bartending school.

“She was a stunner, snow-white skin,” recalls Ronnie Horsman, 85, who ran the Philadelphia Bartending School. “After she took the course she told me she was going to buy a bar on Second Street. I told her ‘Hold on, you should try this out first and see if you like it’ but she had her mind set.”

And so the Khyber Pass was born. Serrill decorated the joint with exotic accents, like the hide of a Bengal tiger that once killed a man on the Ganges and an oversized portrait of Queen Victoria. She covered up the water-damaged ceiling with tented fabric, mounting hand-painted camel skin lamps onto the bar and knocking out two holes in the wall to create a music-performance space next door. She also offered customers an extensive selection of beers, stocking the cooler with nearly 200 brands from around the world.

“That was unheard of at the time, this was way before the craft-beer revolution,” Sloat says. She opened the city’s first wine bar upstairs. Year after year, the Khyber Pass would be voted Best Pub, Best Jukebox and Best Live Music Venue in readers’ polls.
In 1977, Serrill returned to Pakistan and convinced the then teenage Daood to drop out of the military academy he was attending and come live with her in Philadelphia.

“I remember him showing up dressed in white and carrying a cricket bat,” William says. Hours in front of the TV helped soften the culture shock. “I think Daood learned everything he needed to know about the American family from Happy Days.”

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Comments 1 - 3 of 3
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1. Deltios said... on May 19, 2010 at 07:38AM

“Well done! It is a forcefully written and thorough accounting worthy of a 5 star rating. A very complex tale about a fascinating man accused of reprehensible crimes.”

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2. Bravo Lima said... on May 19, 2010 at 08:07AM

Good reporting!

P.S. If that is Ronnies Bartending school that was located on Market street, then I think you have mispelled/mispronounced Ronnie's last name; it is Hoffman.”

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3. Phillip Emerson said... on May 19, 2010 at 03:36PM

“What an fantastic story. I knew that there were reporters hiding somewhere in this country...”


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