New charges against Headley for 2008 Mumbai attacks


David Coleman Headley, and a snapshot from his passport. Images from The Hindu.

In October, 49-year-old Chicago man David Headley (born Daood Gilani) was arrested for his role in planning terrorist attacks against the Danish newspaper Jyllands Posten and two individuals associated with the notorious Muhammad cartoons incident. Subsequent to Headley’s arrest, news broke that he was also being investigated for a possible role in the 2008 urban warfare terror plot that struck Mumbai. On Monday, new federal charges were filed against Headley alleging that he conducted surveillance on behalf of Lashkar-e-Taiba (“LeT”) prior to the Mumbai attacks.

A number of actions are alleged relating to this surveillance. Even the name David Headley is a part of that story: Daood Gilani changed his name to David Headley on Feb. 15, 2006, in Philadelphia “in order to present himself in India as an American who was neither Muslim or Pakistani.” He was able to create a cover story for these surveillance operations: that he was working for First World Immigration Services, an immigration services business based primarily in Chicago. Headley told a person affiliated with First World, who is referred to only as “Individual A” in the complaint, of his assignment for LeT. Individual A gave him permission to open a First World office in Mumbai as a cover, and “instructed an employee of First World to prepare documents to support HEADLEY’s cover story and advised HEADLEY regarding how to obtain a visa for travel to India.”

Headley then traveled to Mumbai five times to undertake surveillance of targets that were later attacked in November 2008, including the Taj Mahal hotel, the Oberoi hotel, the Leopold Cafe, the Nariman House, and the Chhatrapati Shivaji Terminus train station. Following each trip to India, he traveled to Pakistan to provide the results of his surveillance to planners of the November 2008 attack. After being instructed to do so, he also took boat trips in the Mumbai harbor to help determine the best landing sites for the team of attackers who arrived by sea.

The most noteworthy aspect of these new charges is the way a terrorist group was able to make use of a Westerner for surveillance purposes. This is something analysts have been concerned about for years. For example, in his seminal 2007 article on Adam Gadahn, Raffi Khatchadourian wrote that “because of their cultural literacy, and because of the mobility that their citizenship provides,” homegrown terrorists “are potentially the most dangerous of terrorists.” In this case, the planners of the Mumbai attacks believed that Headley’s status as a Westerner and his new name (designed to conceal his Pakistani and Muslim identity) would shield him from suspicion — and not even in the West, but in India.

A second interesting aspect, about which I expect more information to emerge, is the role that US Customs and Border Protection played. A Wall Street Journal article published today notes that Headley “was questioned by an airport inspector in August and deceptive answers about his travels abroad helped officials begin to unravel Mr. Headley’s alleged double life.” The article continues:

A border inspector asked Mr. Headley about his overseas travel, according to court records and people familiar with the case. Mr. Headley said he was working for a company called First World Immigration Service. First World is a business that allegedly provided Mr. Headley with cover as he traveled to scout terrorist targets for Lashkar-e-Taiba, the group responsible for the November 2008 assault in Mumbai, according to the federal charges. Agents searched Mr. Headley’s luggage and found it “contained no papers or other documents relating to such a business,” according to court documents. They also searched tax records and found no record of income paid to Mr. Headley by the company, court records show.

I have already heard some commentators mistakenly state that Headley was arrested right after he lied to CBP officers, which is not the case: his discussion with a border inspector occurred in August, and he wasn’t arrested until October. Rather, the Wall Street Journal states that “the questioning at the airport gave a significant boost to the investigation.” More information about how it bolstered the investigation will be helpful in understanding this case and also interagency cooperation more broadly.

Finally, I am also looking forward to more information about Headley’s previous arrest for heroin smuggling in 1998. Time reports that he was “[c]onvicted on heroin smuggling charges in 1998; Headley later worked for the Drug Enforcement Administration, in part to avoid a lengthy jail sentence.” Just a few years later, he was receiving training from LeT, from Feb. 2002 to Dec. 2003. How much of a missed opportunity was the heroin arrest? Should authorities have suspected at the time that it would have been better to keep Headley incarcerated rather than strike a deal with him?

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  • T Ruth says:

    3 other salient facts:
    1 He is accused of reporting to Ilyas Kashmiri in AQ
    2 Daniyal Gilani the Pakistani Prime Ministers spokesman is Headleys half brother
    3 “Another former military officer is suspected as a co-conspirator and identified only by a pseudonym (Individual A) in the first FBI complaint against Headley. He is said to have recently left the Pakistani Army as a Colonel or Brigadier.” This from wiki…read more at
    On the question of the missed opportunity… well that was in 1998…closer to the Monica Lewinsky years than 9/11
    One hopes that in present times they would get greatly elongated sentences.
    But hats off to the border inspector who first sniffed this character out and hats off to the process that has brought this piece of evil in front of the law.

  • T Ruth:
    The Kashmiri angle is indeed significant, and discussed in the new charges that were brought against Headley. A few snippets from these charges about Headley and Kashmiri: “HEADLEY was introduced to Kashmiri as early as February 2009, and understood that Kashmiri was in regular communication with the senior leadership of al Qaeda…. In or around January 2009 and continuing through May 2009, HEADLEY met with co-conspirators, including Ilyas Kashmiri, on multiple occasions in Pakistan to review his surveillance activity and discuss plans for the attack…. On October 3, 2009, HEADLEY traveled to O’Hare Airport in Chicago, Illinois, intending to ultimately travel to Pakistan in order to meet with, and deliver, the approximately 13 surveillance videos to co-conspirators, including Kashmiri.”
    As for the border inspector, I don’t think it’s correct to say that he first sniffed out Headley. The WSJ is a bit vague on that point, but it’s clear that Headley was on authorities’ radar prior to the airport interview. The WSJ states, for example, that authorities were “already suspicious of him,” but that the interview in which he gave deceptive answers “gave a significant boost to the investigation.” The WSJ continues that “federal surveillance of Mr. Headley, who is an American, accelerated” after the interview.
    How exactly did the interview fit into the investigation of Headley? WSJ is vague on that point, in part because I don’t think they know the answer.


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