An Old City barkeep helped terrorists carry out the 2008 Mumbai attacks.
Still, Daood was shocked by his mother’s libertine lifestyle: the drinking, the revealing clothes, the flirting with men.
“In Islam, human behavior is divided into two categories: ‘halal’ and ‘haram’, the permissible and the forbidden,” William says. “My sister did a lot of things that are ‘haram’.” Serrill’s romantic life was further cause for friction between Daood and his mother. When Serrill found a new love interest, it took precedent over everything else in her life, including Daood, according to William. “She eventually turned her back on David and that was just unforgivable, in my opinion.”
Eventually, Daood assimilated into American life. He enrolled in Valley Forge Military Academy, but lasted just one semester. Friends of his mother believe that it was there that Daood first developed a taste for illegal drugs. He also developed a taste for alcohol, holding court at the Khyber Pass over splits of champagne, romancing a string of young women drawn in by his striking good looks and unusual eyes—one blue, brown.
In 1985, he married a woman he met at the bar, a Penn State grad who lives and works in the area as a real-estate consultant, but who has asked that her name be kept out of news reports. “When he would go to Pakistan he would get all riled up again,” the woman told the Inquirer last fall.
“Infidels. He would use words like that. When he would see an Indian person in the street, he used to spit—spit in the street to make a point.”
Much like his parents’ marriage, this union would not survive the cultural differences; two years later it ended in divorce. “I guess he was torn between two cultures,” she told the Inquirer. “I think he liked both. He didn’t know how to blend them.”
By 1987, hobbled by health issues and business difficulties, Serrill put the bar up for sale. It was eventually purchased by the Simons family. Brothers Steve and Dave Simons assumed management duties and the Khyber re-opened in the fall of 1988. Under their stewardship, the Khyber would become a local mecca of indie-rock with a national rep among touring bands as the place to play in Philadelphia.
Meanwhile, Daood and his mother started a video-store business called Flik’s, which would deliver rental videos to your doorstep. He also became involved in less legitimate forms of commerce.
“He got involved with some bad people, which is not unusual when you live above a bar,” William says. Returning from a trip to Pakistan in June 1988, he was arrested at the airport in Frankfurt, Germany, when customs agents discovered two kilos of heroin hidden in the false bottom of his suitcase. Daood was turned over to the DEA and quickly agreed to cooperate in return for a lighter sentence. Two days later, he was back at his apartment on New Street, which had been wired for sound and video by the DEA, handing the suitcase of heroin over to two drug associates just before the feds pounced. In return for his cooperation, his sentence was cut in half, to four years. He was released on probation in 1992 and his passport returned to him so that he could return to Pakistan to proceed with an arranged marriage to a woman named Shazi, who would eventually bear him four children. But Daood had a hard time meeting the terms of his release, and after flunking a series of drug tests, he was sent back to prison in 1995 for six months. Two years later, he was again arrested by the DEA for smuggling heroin from Pakistan into the United States, and quickly agreed to wear a wire when he delivered the drugs to dealers in a New York hotel room.
Despite this being the second time he was arrested for the same felony, he was sentenced to just 15 months. The man he delivered the drugs to, James Leslie Lewis, was sentenced to 10 years. In exchange for his light sentence, Headley worked as a confidential witness, ensnaring three low-level drug dealers in heroin buys. Within six months, Headley was released and allowed to travel to Pakistan, where he collected intelligence on the heroin trade for the DEA, according to the Inquirer.
“The people he was fingering were very scary people, very high up in the Pakistani drug trade,” William says. In exchange, his probation, originally intended to extend to 2004, ended in December of 2001. “Daood told me that when he got busted the second time he told himself that if he got out of this, he would give his life over to Allah. I don’t think he ever took a drug or a drink again.”
Two months later, he was back in Pakistan, this time attending a Lashkar-e-Taiba training camp, where he received a three-week ideological course on the merits of waging a jihad. Over the course of the next year, he returned to Pakistan four more times for jihadist training. In August 2002, he attended a three-week course on the use of weapons and grenades and other skills. In April 2003, he attended a three-month course on close-combat tactics, use of weapons and grenades, and survival skills. In August 2003, he attended a three-week course on counter-surveillance. Finally, in December 2003, he attended a three-month course on combat and tactical training.
In 2005, he began conspiring with LET operatives in Pakistan to stage a spectacular attack inside India. It was determined that his role in the plot would be to travel to India repeatedly, scoping out targets and videotaping locations and recording GPS coordinates that would guide a team of assassins to the various killing zones. In February 2006, he legally changed his name from Daood Gilani to David Coleman Headley to make it easier to travel back and forth from Pakistan to India without raising red flags at security. He would dress western and, if asked, he would present himself as an American Jew. Before heading to India, he moved his family to Chicago, telling relatives in Philadelphia that he wanted to raise his children Muslim, and there was a much larger Islamic community with better school options in the Windy City. It’s more likely he moved to Chicago to forge an alliance with Tahawwur Hussain Rana, a friend he first met as a cadet at military school back in Pakistan.
Rana owned and operated First World, an immigration service for Pakistani nationals. Headley would claim he was setting up an office for First World if anyone asked him about the nature of his business in India. All told, he made five extended trips to Mumbai—in September 2006, February and September 2007, and April and July 2008—returning each time to Pakistan to drop off the videotapes with LET operatives.
In November 2008, just weeks before the Mumbai terror attacks were scheduled to commence, Headley was instructed by LET operatives to fly to Denmark and conduct reconnaissance on the Jyllands-Posten newspaper. Headley entered the offices of the paper under the pretense of placing an ad for Rana’s First World Immigration Service. When he returned to Pakistan, he turned over his videotapes to LET operatives. They discussed the scope of the operation. Headley, according to authorities, thought they should only target those directly responsible, specifically the cartoonist and the editor. One LET operative told him: “All Danes are responsible,” according to court documents.
In the wake of all the heat generated by the Mumbai attacks, LET chose to put the Copenhagen attack on the backburner. One of the LET operatives, Ilyas Kashmiri, told Headley that if LET didn’t want to proceed, he knew people in al-Qaeda who did. In May 2009, Headley met with Kashmiri in Waziristan. Kashmiri told him he had spoken with the senior al-Qaeda leadership and that they wanted the Copenhagen operation to happen as soon as possible. He directed him to a European contact who would provide money, weapons and manpower. Kashmiri instructed Headley to tell the European contact that the gunmen should prepare martyrdom videos; this would be a suicide mission.
In July 2009, Headley flew to Denmark for final surveillance of the newspaper offices, and established contact with the man who would provide the weaponry and manpower for the attack. He laid low in Chicago for a couple months, reportedly meeting with Rana and keeping him apprised of the plot. They spoke in code, referring to the Copenhagen plot as the Mickey Mouse Project.
But it all came to an end Oct. 3, 2009, when Headley was arrested at Chicago’s O’Hare airport, attempting to board a flight bound for Philadelphia. From there, he was to fly to Pakistan. In his luggage, authorities found video footage of the Danish newspaper offices on a memory stick, and the front page of an edition of the paper. That same day, authorities arrested Rana.
In exchange for his guilty plea and full cooperation, Headley was spared the death penalty and extradition to India or Denmark. He will not be sentenced until after testifying against his old friend Rana, who has pled not guilty and is scheduled to stand trial in the beginning of November.
“I believe Daood’s upbringing damaged him in a way that he never really stood a chance in life,” William Headley says. “His father was unbelievably strict; he lived and died by the Koran. His mother was a libertine, her creed was ‘if it feels good, do it’. And he was never able to reconcile those two worlds, because they can’t be reconciled. There is a reason he was a heroin addict. And there is a reason he became a jihadist. I have to believe that—it’s the only way I can make peace with what happened.”
Jonathan Valania is the editor-in-chief of Phawker.com
PW's Summer Guide 2015