“He just turns around immediately and betrays everybody when it’s convenient for him,” said Sageman.
Struggling with addiction, Headley spent six months in prison for a probation violation in 1995. He moved to New York, where he bought and operated video stores. Despite his criminal record, he managed to avoid prosecution a year later when police on Long Island arrested him for allegedly assaulting and threatening the former boyfriend of his new Canadian girlfriend, according to Nassau County authorities.
Chapter 2: Informant and Militant
Headley overcame his addiction but not his taste for drug money.
In early 1997, the DEA arrested him in a sting at a Manhattan hotel. He signed up as a confidential DEA informant and was out on bail by August. In January 1998, the DEA sent Headley to Pakistan to dispel suspicions among traffickers about his absence. He used his wealthy father’s house in Lahore to meet with suppliers, and gathered useful intelligence during his first and only DEA-funded mission in Pakistan, the senior DEA official said.
“This was the only trip at the DEA’s behest,” the senior official said.
During his first 16 months as an informant, Headley infiltrated Pakistani heroin trafficking networks, generating five arrests and the seizure of 2½ kilos of heroin, the DEA says.
There were warning signs, however. He broke the rules by trying to set up dealers with jailhouse phone calls that were not monitored by agents, according to court records. He angled for leverage with his handlers, according to a close associate from that period.
“The DEA agents liked him,” the associate said. “He would brag about it. He was manipulating them. He said he had them in his pocket.”
One defendant was acquitted on grounds of entrapment, a rare finding in a drug case. Ikram Haq was a mentally impaired Pakistani immigrant. His lawyer, Sam Schmidt, convinced the jury that Headley conned his client into a heroin deal.
“My impression of him was a person who was in many ways a sociopath,” Schmidt said, “that he would be able to say anything that he thought would work to his benefit.”
Headley served another eight months in prison. He became a more devout Muslim behind bars, according to his associate. Soon after his release in 1999, probation officials permitted him to travel to Pakistan for a few weeks for an arranged marriage. His new wife remained in his family hometown of Lahore.
Headley returned to New York and resumed work for the DEA in early 2000. That April, he went undercover in an operation against Pakistani traffickers that resulted in the seizure of a kilo of heroin, according to the senior DEA official.
At the same time, Headley immersed himself in the ideology of Lashkar-i-Taiba. He took trips to Pakistan without permission of the U.S. authorities. And in the winter of 2000, he met Hafiz Saeed, the spiritual leader of Lashkar.
Saeed had built his group into a proxy army of the Pakistani security forces, which cultivated militant groups in the struggle against India. Lashkar was an ally of al Qaeda, but it was not illegal in Pakistan or the United States at the time.
Saeed made a statement that was Headley’s epiphany: “One second spent in jihad is superior to 100 years of worship and prayer.”