Prosecutors say Tahawwur Rana provided cover for a former boarding school friend who served as a scout for the terrorists who carried out the 2008 attack. The scout is a Pakistani-American who is now cooperating with the United States. David Coleman Headley told interrogators that Pakistan's Interservices Intelligence Agency provided training and funds for the Mumbai attack.
That means the Chicago trial may further strain ties between the U.S. and Pakistan. Those ties have been especially tense since American forces killed Osama bin Laden in a Pakistan compound.
Court proceedings begin Monday with jury selection. Though the accusations against Rana are fairly straightforward, the implications of the trial could be enormous.
To make their case, federal prosecutors may lay out alleged ties between Lashkar-e-Taiba, the militant group blamed for the attacks, and Pakistan's Inter-Services Intelligence agency, known as the ISI. The trial comes amid growing suspicion that the ISI was complicit in harboring bin Laden, who was killed by Navy SEALs during a May 2 raid, and could lead to further strains in the already frayed relations between Pakistan and the United States.
The key government witness could be Headley, who has a troubled past and pleaded guilty last year to laying the groundwork for the Mumbai attack by Lashkar-e-Taiba.
Headley told authorities that Rana provided him with cover for a series of scouting missions he conducted in Mumbai. Headley also told interrogators that he was in contact with another militant, who has ties to al-Qaida, as part of a separate plot to bomb a Danish newspaper that printed cartoons that offended Muslims.
"What you'll have now in Chicago is a trial which will undoubtedly demonstrate links between Pakistan government agencies and one of the most competent terrorist organizations operating in South Asia -- Lashkar-e-Taiba," said Seth Jones, a senior political scientist at the RAND Corp. The trial "just adds more fuel to an already tense situation."
Nearly 100 potential jurors are expected at Chicago's federal courthouse Monday. They'll be asked to fill out forms with a range of questions, from personal views on Islam to knowledge of Pakistani militant groups. Jury selection is expected to last several days.
Experts say Lashkar-e-Taiba, which means "Army of the Pure," was created with the ISI's help in the 1980s as a proxy fighting force to battle with India over the disputed territory of Kashmir. Counterterrorism officials say the group has gained strength with the help of the ISI since then, possibly with the help of retired officers. Pakistani officials have denied any ties with the group.
Lashkar-e-Taiba is accused of carrying out the three-day siege in Mumbai in which 10 gunmen attacked two luxury hotels, a Jewish center and a busy train station in India's financial capital, killing 166 people, including six Americans.
Rana, a Canadian national who has lived in Chicago for years, owns a Chicago-based First World Immigration Services, in the city's South Asian enclave. He and Headley met as teenagers at a Pakistani military boarding school outside Islamabad.
Prosecutors say Rana, who was arrested in 2009, provided cover for Headley by letting him open a First World office in Mumbai and travel as a supposed representative for the agency. He also allegedly helped Headley make travel arrangements as part of the plot against the Danish newspaper that in 2005 printed cartoons of the Prophet Muhammad, which angered many Muslims worldwide.
Rana is charged with providing material support for terrorism in India and Denmark. In court documents, Rana's attorneys have said he believed Headley was working for Pakistani intelligence. Headley also told authorities that he told Rana he "had been asked to perform espionage work for the ISI," according to a court filing.
"Part of the defense will be that Headley used his connections with ISI to explain the things he was doing," Rana's attorney Patrick Blegen told reporters last week. Rana "has maintained his innocence since the day he was arrested."
However, U.S. District Court Judge Harry Leinenweber ruled that that proposed defense was "objectively unreasonable."
Prosecutors have declined to comment ahead of the trial. A senior Pakistani intelligence official said he hasn't been following the trial and didn't have comment on it.
Some experts doubt the trial will reveal much, saying federal prosecutors may work hard to keep sensitive information from surfacing in the courtroom, and Headley is not the most credible witness. Headley reached a plea deal with prosecutors in the terrorism case in exchange for avoiding the death penalty and previously had been an informant for the U.S. Drug Enforcement Administration after a drug conviction.
Details of Headley's possible testimony were revealed last year in an Indian government report detailing what he had allegedly told Indian investigators during questioning in Chicago.
In the report, Headley is cited describing how the ISI was deeply involved in planning the Mumbai attacks and how he reported to a man known only as "Major Iqbal," whom he called his Lashkar "handler." But some experts have suggested Iqbal could be a retired ISI officer, or that he may not even exist. In the indictment, his name is listed as unknown, and he's referred to only under the alias "Major Iqbal."
Rana is actually the seventh name on the indictment, and the only defendant in custody. Among the six others charged in absentia are "Major Iqbal" and Sajid Mir, allegedly another Lashkar-e-Taiba supervisor who also "handled" Headley.
Also indicted is Ilyas Kashmiri, the commander of the terror group Harakat-ul Jihad Islami who also is believed by Western intelligence to be al-Qaida's operational chief in Pakistan. During his travels for spying and training, Headley allegedly met with Kashmiri in Pakistan, and Kashmiri gave him instructions on how to carry out the Danish newspaper bombing, which ultimately never occurred.
(The Associated Press contributed to this report.)