The transcript of the Nov. 16, 2001, hearing does not resolve the disputed versions. The prosecutor apparently did not know about Headley’s extremism, unauthorized travel or the task force interview weeks before; he called him an “outstanding supervisee” with “no problems.” The judge said probation was being ended “for the purposes of him returning” to Pakistan, and mentioned Headley’s “continuing cooperation.”
In the frenzied aftermath of Sept. 11, U.S. intelligence agencies were scrambling to recruit spies. With his language skills, Pakistani connections and undercover talents, Headley had potential. A U.S. law enforcement official familiar with the case said he doubts the government ended the probation early just to reward Headley, and even let him leave the country, because he suddenly decided to stop being an informant.
“It’s preposterous,” the official said. “It defies any sort of logic at all. U.S. attorneys are not in the business of granting presents for people. In the post-9/11 environment, there was a big push for intelligence assets.”
A number of DEA informants moved to counterterror work during that period. Some were passed to the FBI or CIA, and a few were run jointly by the DEA with other agencies, according to former U.S. law enforcement and intelligence officials.
In fact, a counterterror source said the DEA had discussions with the FBI and other agencies in late 2001 about which agency could best use Headley. The discussions cited his allusion to a relative in the ISI as a potential benefit, the counterterror source said.
During his testimony this year, Headley said nothing about deciding to end his service as an informant before going to Pakistan. Asked when he stopped working for the DEA, he testified: “The following year, in September. … It was the time that I had signed up for.”
The world of informants is hazy, according to law enforcement veterans. Agents at the DEA, FBI and other agencies sometimes use unofficial “hip-pocket” sources, the veteran officials said. Ex-informants sometimes surface and provide intelligence. Or they try to use past relationships with the government to justify their behavior when they get in trouble.
Officials at other agencies say Headley remained a DEA operative in some capacity as late as 2005. The senior DEA official denied that, citing the agency’s detailed records on informants. He said he had no information on whether Headley shifted to intelligence work for another agency but would not rule out that possibility.
The CIA and FBI deny that Headley worked for them. Today, nobody wants any part of him.
Chapter 4: The Path to Holy War
By February 2002, Headley was training in Lashkar’s mountain camps. He did a three-week introductory course on ideology and jihad.
The U.S. and Pakistan had outlawed Lashkar. But the ISI continued to fund, train and direct the group, which refrained from attacking Pakistan. The group’s global networks and storefront offices in Pakistan made it easier to join than al Qaeda. Lashkar camps churned out thousands of militants, some of whom went on to lead al Qaeda plots in the West.
That summer, Headley returned to New York and proposed to his Canadian-born girlfriend with a diamond ring in Central Park. Photos show he had bulked up and grown a long beard. His sharp profile and receding, slicked-back hair gave him a hawk-like look.