One June day in 1988, customs agents at the Frankfurt, Germany, airport pulled aside an intense and striking young man waiting to get on a plane back home to Philadelphia.
They suspected he had heroin in his suitcase. They were right -- two kilos' worth from Pakistan, hidden under a false bottom. He wasn't tough to crack: Before the day was out, Daood "David" Gilani decided to save his own skin, agreeing to betray his drug-dealing partners by helping U.S. drug agents set up a sting.
It was the beginning of a complicated, off-and-on relationship as a confidential informant with the Drug Enforcement Administration -- one that lasted more than a decade.
In fact, Gilani was so helpful as a DEA informant in the late 1990s on heroin imported from Pakistan, according to records and Inquirer interviews, that prosecutors made a rare move: They ended his probation years early, allowing him to travel freely. Within weeks, investigators say, he began training with terrorists in Pakistan.
His latest arrest ended just like his first. On Oct. 3, FBI agents in Chicago approached the man -- by now, he had changed his name to David Coleman Headley -- just before he stepped on a plane for Philadelphia. This time, the FBI had questions about terrorism, not heroin.
Once again, Headley immediately switched sides. Prosecutors say he admitted taking trips to the jihadist camps and performing surveillance and photo reconnaissance for terrorist plots in Denmark and India, including preparations for the deadly 2008 Mumbai attacks.
Today, the man who came to Philadelphia as a teenager and grew up over an Old City nightspot is in federal prison in Chicago, charged with murder. He has pleaded not guilty. The FBI says Headley's videos and photographs were used by the squad of terrorists who killed 170 people in Mumbai, India, last year.
By talking this time, Headley might escape the death penalty.
New details are emerging about the strange double life of Headley, the son of a Pakistani broadcaster and a Main Line socialite who would spend evenings holding court and drinking splits of champagne in her bar, the Khyber Pass.
He was briefly married to a Philadelphia woman in the 1980s whom he met at the bar, who, like a lot of other young women, was mesmerized by his dark skin and piercing eyes -- one blue, the other brown.
He later became a heroin addict, and twice was caught smuggling the drug into the country by the DEA, in 1988 in Frankfurt, Germany, and in 1997 in New York. Both times, he got off with a lighter sentence by testifying against his partners.
It quickly became clear to federal law enforcement officials in New York that Headley knew a great deal about the heroin trade between the United States and Pakistan and was willing to cooperate.
Headley went to work for DEA, making heroin cases against at least three Pakistani men, according to records and interviews.
In one, as agents recorded the conversation, he began yelling at a man who was reluctant to get involved.
"Oh, brother, I do not want to do anything illegal," said the man, who was eventually acquitted. "You know that if anything happens - my wife is sitting with little, little kids."
Immediately after his release from federal prison in 1999, he traveled to Pakistan with government permission, court records show.
"We don't identify any of our confidential sources," said Erin McKenzie-Mulvey, a DEA spokeswoman.
To the agents who knew him then, he was a common drug-dealing "opportunist," someone who knew how to forget about loyalty, cut his losses, and get the best deal.
"Wow! Get out! I would have bet my last $100 he wouldn't get involved in terrorism," said one law enforcement official who worked on the 1988 Philadelphia case.
"Guys like this, they know the system," the official said.
Between two worlds
To relatives and family friends, it was no surprise that Headley ended up torn between different worlds.
"David and Daood; they're like two different people," said his uncle William Headley of Cochranville. He said his nephew had "an upbringing that was irreconcilable."
David Headley was born in 1960 in Washington to a couple who met while working at the Pakistani Embassy. His mother, Serrill Headley, was a 19-year-old Bryn Mawr woman with a memorable laugh and a taste for adventure.
The family soon moved to Pakistan, but Serrill Headley chafed at the strictures of life with Syed Saleem Gilani, who, her friends said, had a traditional Islamic view of a woman's place in the home. She left in 1968, without 8-year-old Daood and a younger daughter.
"She was too young, too free, too independent," said William Headley, who operates a day-care center in Nottingham.
He said his family was devastated by his nephew's alleged involvement with terrorists. "We don't deserve to be linked to terrorism," he said.
Serrill Headley went to a bartending school and later bought an old pub on Second Street near Chestnut that she rechristened the Khyber Pass.
"Beautiful woman," said Ron Horsman, who owned the bartending school. "She had snow-white skin, and then the dark hair. She was like Rosalind Russell in the old movies."
Horsman and other friends said she talked constantly about getting her children back. In 1977, she finally succeeded in persuading Daood to leave his military school in Pakistan to come live with her in Philadelphia.
The reunion wasn't a smooth one. She would talk to him lovingly in Urdu. William Headley remembers a young man watching Happy Days when he was alone above the bar.
But Daood, shocked at his mother's wild ways, struggled to fit into his new life in America.
He enrolled in the Valley Forge Military Academy but lasted only one semester; one family friend said he got involved with drugs there. He later took accounting classes at Philadelphia Community College, but did not earn a degree.
He reminded one of his mother's friends of Holden Caulfield, the main character in The Catcher in the Rye, trying to fit in and not succeeding. He quickly attracted a flock of girlfriends, though.
"In those days he was a rare plant compared to the guys from Kensington," said Kiki Olson, a friend of Serrill Headley's.
In 1985, he married a woman who had recently graduated from Pennsylvania State University and began working at the Khyber as a bartender.
Like his parents' marriage, Daood's quickly ran aground on the couple's sharp cultural conflicts.
"When he would go to Pakistan he would get all riled up again," said the woman, now a real estate consultant in Chester County. Long since remarried, she spoke on condition that her name not be used.
"Infidels. He would use words like that," she said. "When he would see an Indian person in the street, he used to spit, spit in the street to make a point.
"I guess he was torn between two cultures," she said. "I think he liked both. He didn't know how to blend them."
They divorced in 1987.
By the next year, he was in business as a drug mule for Philadelphia dealers.
In Frankfurt, Germany, the DEA agent stationed there was summoned to the airport and interviewed Headley, then still named Gilani, whom he remembered as "very, very quiet and very controlled." The agent told him he could help himself by cooperating. Gilani agreed.
Two days later -- after his apartment on New Street had been wired for sound and video -- he delivered the suitcase to Richard Roundtree and Darryl "Tarik" Scoggins.
"Is this all ours?" Scoggins asked, pointing to the pile of heroin on the coffee table. He gave Gilani a high five.
Gilani got his sentence cut in half to four years. At his sentencing, the judge said he was giving him a break because of his cooperation, because he didn't have a record -- and because he had a heroin habit.
"It's up to you, Mr. Gilani, to do what you can with the rest of your life," said the judge, the late James McGirr Kelly. "You are still a young man."
Released from prison in 1992, he asked the judge for his passport back. "In accordance with his heritage," he planned to go to Pakistan for an arranged marriage, his probation officer wrote.
But he had trouble staying clean and flunked drug tests. He was sent back to drug treatment in 1994 and, in 1995, got an additional six months in jail.
Two years later, Headley was arrested for nearly the same crime -- moving heroin from Pakistan to America. This time, he was caught by the DEA on his way to deliver heroin to New York dealers, and once again, he agreed to cooperate, wearing a wire as he delivered the heroin in a hotel room.
Headley pleaded guilty and received a 15-month sentence. The dealer he turned on, James Leslie Lewis, got 10 years.
To get such a reduced sentence, Headley didn't only testify against Lewis. According to court records, he worked for the DEA as a confidential witness, setting up at least three heroin deals.
"It was easy for him because he was of both worlds," said a law enforcement source who was involved in the New York heroin case.
Just a month after he pleaded guilty to the New York crime in 1997, Headley worked with the DEA, records show, to induce a fellow Pakistani living in New Jersey into buying heroin. The man, Ikram Haq, had a low IQ and didn't speak much English. Headley had befriended him when they served together in prison.
At the 1998 trial in New York, it was Headley's word against Haq's. The jury acquitted Haq, providing a rare victory to a defendant claiming entrapment.
Headley "was a common run-of-the-mill drug dealer informant who got caught and was simply trying to save his own neck," recalled Haq's attorney, Sam A. Schmidt. What made it unusual, he said, was how the DEA allowed Headley to "overreach" to target a vulnerable man.
In another 1998 case, Headley worked as a confidential informant against Zaheer Babar, who pleaded guilty to flying to Lahore, Pakistan, and smuggling one kilo of heroin into New York, hiding it inside seven books in his luggage. Babar got 31/2 years.
Headley began serving his 15-month sentence at Fort Dix in November 1998. But within six months, records show, Headley was out of jail and headed to Pakistan for a monthlong trip -- all with the approval of a federal judge and the Department of Justice.
The original sentence called for Headley to remain on probation five years, until mid-2004.
But at the end of 2001, his attorney and the prosecutor together asked the judge to end his probation early. The judge agreed.
"Eight or nine times out of ten, when you see a scenario like that, it's because he's cooperating or being rewarded for past cooperation," said former federal prosecutor Rocco Cipparone. "If he's still an informant, it makes it easier for everyone -- for example, you don't need the court's permission to travel."
Less than 60 days later, the FBI now alleges, Headley was back in Pakistan, this time doing more than dealing drugs: He was training with the terrorists.
The U.S. government alleges that Headley attended camps of Lashkar-e-Taiba, "The Army of the Good," in February and August 2002 and three times in 2003.
In February 2006, he went to court in Philadelphia to change his name from Gilani to Headley, saying he wanted to take his mother's name to match "the name he has been known as in business for approximately the previous 10 years."
According to the FBI, though, he admitted that he did it so he could travel more easily in India. He also picked up a new passport.
Starting in 2006, Headley traveled to Mumbai to perform surveillance for Lashkar, prosecutors allege. They say he videotaped targets, including the train station and Taj Mahal and Oberoi hotels.
Last year, 10 Lashkar terrorists attacked the hotels and train station, killing 170 people, including six Americans. Headley potentially faces the death penalty for those six murders.
Americans Linked to Terror Cases
The Headley case is just one of a number of recent cases in which Americans have been linked to terrorist acts here and overseas.
Last month, officials alleged a plot by Minnesotans to recruit American teens for terror cells in Somalia, and a U.S. Army major, Nidal Hasan, was charged with killing 13 soldiers at Fort Hood, Texas. This followed arrests this year for alleged terror plots in Denver, Boston, and Dallas.
Last year, five foreign-born men raised primarily in Cherry Hill were convicted of plotting an attack on Fort Dix soldiers.
"It's really disturbing -- Americans becoming radicalized," said Sen. Bob Casey (D., Pa.), chairman of the Foreign Relations subcommittee on South and Central Asia. "It's not something we're used to, even after the attacks of 9/11."
Five young Americans were arrested last week in Pakistan for allegedly planning to attack U.S. soldiers in Afghanistan.
Rep. Charles W. Dent (R., Pa.), a senior member of the Homeland Security Committee, said the recent cases demonstrated that "this jihad movement is a global threat -- we're more susceptible than we thought."
- John Shiffman