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The American Behind India’s 9/11—And How U.S. Botched Chances to Stop Him

Agents were canvassing sources for information on the al Qaeda attacks of the day before. Headley angrily said he was an American and would have told the agent if he knew anything, according to the senior DEA official.

Headley began collecting counterterror intelligence, according to his testimony and the senior DEA official. He worked sources in Pakistan by phone, getting numbers for drug traffickers and Islamic extremists, according to his testimony and U.S. officials. He visited a mosque in Queens at the direction of the DEA, according to his testimony and officials.

But there was a dark side. A former girlfriend of Headley’s told a bartender named Terry O’Donnell that he wanted to go to Pakistan to fight alongside Islamic militants, according to law enforcement officials. She said he had praised the Sept. 11 attacks, recalled O’Donnell, now a New York firefighter.

“And then she went on and said he was happy to see it happen,” O’Donnell said in interview. “And he got off on watching the news over and over again.”

O’Donnell contacted an FBI-led task force that was investigating 9/11 — and an avalanche of tips. Residents of the traumatized city were reporting everything from people who spoke Arabic to neighbors who put out the garbage at odd hours. Investigators interviewed Headley’s mother and the girlfriend, who described his ideological support for militants in Kashmir, according to officials.

It would be the only warning about Headley that resulted in an interrogation. On Oct. 4, two Defense Department agents working for the task force questioned him in front of his DEA handlers at the drug agency’s office, according to the senior DEA official.

Headley denied the accusations and cited his counterterror work, according to U.S. officials. He told the agents he had a distant Pakistani relative who was an Army general and the deputy director of the ISI, that nation’s powerful intelligence service, according to U.S. and Indian officials.

Today, U.S. intelligence believes the relative may have been Gen. Faiz Gilani, the ISI’s deputy director at the time, according to a U.S. counterterror official. The suspected family connection has not been confirmed, the counterterror official said. But it was a portentous detail.

The investigators cleared Headley. Although their informant had been interviewed by the FBI task force, the DEA handlers did not write a report, the senior DEA official said. In addition, he said the DEA has no record that agents looked into Headley’s claim about the ISI relative to determine whether it had intelligence value or, conversely, might show he was a liar.

Six weeks later, another unusual thing happened. A federal judge ended Headley’s probation three years early so he could travel to Pakistan. A transcript and accounts of participants show the hearing was rushed. Headley’s lawyer told the judge he had “just been handed all sorts of material.” A supervisory probation officer, Luis Caso, apologized because he had not had time to dress appropriately for court.

“Having a probation terminated early is rarely done. It’s usually reserved for someone who’s very ill,” Caso said in an interview. “It was a last-minute thing.”

The government was in a hurry, said Caso, who is now retired.

“From what I remember, it’s basically he was a very good cooperator at that time, working with the DEA, and he was going to do more of the same but overseas in Pakistan,” he said. “It was shortly after 9/11 occurred, and at that time, all the federal law enforcement agencies were doing their very best to investigate the terrorist activity, and whoever they had under their control for information purposes they had utilized to the maximum.”

Headley’s lawyer has a similar recollection. Howard Leader said prosecutors called him a few days earlier to tell him the hearing would take place.

“The fact that this was coming from the government, that was, frankly, highly unusual,” Leader said. “It’s the only occasion I can recall it ever happening.”

Leader said he believed the DEA had made the request and that Headley would continue working for the agency in Pakistan.

“My recollection is, basically, it’s a twofold mission,” Leader said. “There would be drug-related work specifically. But also, in light of the then-very-recent events on September the 11^th, I think that he was going to go back to Pakistan with a view towards meeting with or gathering whatever information he could that might be useful to the U.S. government regarding certain extremist elements there.”

An excited Headley told friends and family that he was leaving on a mission. He explained that “the FBI and DEA had joined forces” and he would work for them in Pakistan, according to his close associate.

The DEA gives a far different account. The senior DEA official said Headley told his handlers he wanted to return to Pakistan for family reasons. The senior official said the DEA agreed to support ending his probation because of his past cooperation. The DEA provided a letter to the judge describing his work on drugs and counterterrorism, according to U.S. officials and others familiar with the case.

The DEA then deactivated him as a law enforcement informant, a process that became official on March 27 of the next year, according to the senior DEA official. Headley was paid a total of $3,925 while an informant, the senior official said. DEA agents did not work with him again after the hearing, the senior official said.