An accused plotter with feet in East and West

The trip from a strict Pakistani boarding school to a bohemian bar in Philadelphia has defined David Headley’s life, according to those who know the middle-age man at the center of a global terrorism investigation.

Raised by his father in Pakistan as a devout Muslim, Headley arrived back here at 17 to live with his American mother, a former socialite who ran a bar called the Khyber Pass.

Today, Headley is an Islamic fundamentalist who once liked to get high. He has a traditional Pakistani wife, who lives with their children in Chicago, but also an American girlfriend, a makeup artist in New York, according to a relative and friends. Depending on the setting, he alternates between the name he adopted in the United States, David Headley, and the Urdu one he was given at birth, Daood Gilani. Even his eyes — one brown, the other green — hint that he has roots in two places.

Headley, an American citizen, is accused of being the lead operative in a loose-knit group of militants plotting revenge against a Danish newspaper that published cartoons of the Prophet Muhammad. The indictment against him portrays a man who moved easily between different worlds. The profile that has emerged of him since his arrest, however, suggests that Headley felt pulled between two cultures and ultimately gravitated toward an extremist Islamic one.

“Some of us are saying that ‘Terrorism’ is the weapon of the cowardly,” Headley wrote in an e-mail message to his high school classmates last February. “I will say that you may call it barbaric or immoral or cruel, but never cowardly.”

He added, “Courage is, by and large, exclusive to the Muslim Nation.”

Headley’s e-mail messages, including many that defend beheadings and suicide bombings as heroic, are among the evidence in the government’s case against him and his accused co-conspirator, Tahawwur Hussain Rana, who was born in Pakistan, is a citizen of Canada and runs businesses in Chicago.

The men, who became close friends in a military academy outside Islamabad, were arrested in October in Chicago. They are charged with plotting an attack they labeled the Mickey Mouse Project against Jyllands-Posten, the Danish newspaper whose cartoons had provoked outrage across the Muslim world.

Since then, the investigation has widened beyond Chicago and Copenhagen. The authorities have learned more, with cooperation from Headley, about the two men’s network of contacts with known terrorist groups, including al-Qaida and Lashkar-e-Taiba, a Pakistani militant group, as well as officials in the Pakistani government and military. American and Indian investigators are also looking into whether the two Chicago men, who traveled to Mumbai before the deadly assault there last November, may have been involved in the plot.

Headley, 49, and Rana, 48, stand out from the young, poor extremists from fundamentalist Islamic schools who strike targets in or close to their homelands; they stand out for their privileged backgrounds, extensive travel and bouts of culture shock.

Rana’s father is a former principal of a high school outside Lahore. One of his brothers is a Pakistani military psychiatrist who has written several books, and another is a journalist at a Canadian political newspaper, The Hill Times.

Trained as a physician, Rana immigrated to Canada in 1997 and became a citizen a few years later. Then he moved his wife and three children to Chicago, where he opened a travel agency that also provided immigration services.In 2002, he started a Halal slaughterhouse that butchers goats, sheep and cows according to Islamic religious laws.

Neighbors described Rana as a recluse who rarely spoke to anyone and whose children never played with others on the street.

Those who knew Headly the other indicted conspirator paint atroubled image.  “Most people have contradictions in their lives, but they learn to reconcile them,” said William Headley, an uncle who owns a day care center in Nottingham, Pennsylvania. “But Daood could never do that. The left side does not speak to the right side. And that’s the problem.”

Daood Sayed Gilani was born in Washington, where his parents worked at the Pakistani Embassy. Friends of the family said his father, Sayed Salim Gilani, a dashing diplomat and an avid musicologist and poet, charmed his way into the heart of Serrill Headley, who had left Philadelphia’s Main Line to work as a secretary at the embassy.

In 1960, the couple and their infant son, Daood, left the United States bound for England aboard the ship America, and from there went on to Lahore. But the marriage quickly soured, friends said, as Gilani immersed himself in the traditions of his homeland and his bride refused to submit to them.

She arrived back in Philadelphia, friends said, in the early 1970s, taking different office jobs and dating wealthy suitors until one of them lent her money to buy an old bar. She turned it into the Khyber Pass, decorated with billowing Afghan wedding tents and stocked with exotic beers.

In 1977, Pakistan’s government was overthrown in a military coup, and Headley, friends said, feared for her children. She traveled to Pakistan, withdrew Daood from the Hasan Abdal Cadet College and brought him to live with her, a move recorded by The Philadelphia Inquirer. (Her daughter, Syedah, stayed behind with her father for several years.)

According to family friends, the teenager soon rebelled against his mother’s heavy drinking and multiple sexual relationships by engaging in the same behavior.

Later, said Lorenzo Lacovara, another former worker at the bar, Gilani began expressing anger at all non-Muslims.

“He would clearly state he had contempt for infidels,” Lacovara said in a telephone interview from New Mexico. “He kept talking about the return of the 14th century, saying Islam was going to take over the world.”

In 1998, Gilani, then 38, was convicted of conspiring to smuggle heroin into the country from Pakistan. Court records show that after his arrest, he provided so much information about his own involvement with drug trafficking, which stretched back more than a decade, and about his Pakistani suppliers that he was sentenced to less than two years in jail and later went to Pakistan to conduct undercover surveillance operations for the United StatesDrug Enforcement Administration.

In 2006, Gilani changed his name to David Headley, apparently to make border crossings between the United States and other countries easier, court documents say. About that time, his uncle said he moved his family to Chicago because it had a large Muslim community and he wanted to send his four children to religious schools.

There, the family lived in a small second-floor apartment. Headley claimed to work for Rana’s immigration agency.  Earlier this year, Headley complained in an e-mail message about “NATO criminal vermin dropping 22,000 lbs bombs on unsuspecting, unarmed Afghan villagers” or “napalming southeast Asian farmers.” Writing about Pakistan’s chief enemy, he said, “We will retaliate against India.”

And in an e-mail message defending the beheading of a Polish engineer by the Taliban in Pakistan, he wrote, “The best way for a man to die is with the sword.”

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