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In this courtroom sketch, Tahawwur Hussain Rana, charged with plotting a terrorist attack on a Danish newspaper, appears before federal Magistrate Judge Nan Nolan on Wednesday, Dec. 2, 2009, in Chicago. Nolan, saying she wanted to study the evidence, postponed a decision on whether to set bond for Rana at least a week.Verna Sadock

He was a pillar of Chicago's South Asian community, a mysterious Canadian known as a healer. He flew a Maple Leaf flag in front of his immigration consultancy that was a go-to spot to sort out visa woes. A few blocks away on Devon Avenue, Muslims patronized his halal meat shop, which was stocked from his abattoir on the outskirts of town.

That was before his arrest two years ago.

On Monday, in a case that offers a window on frayed U.S.-Pakistani relations, an American court will hear testimony that Tahawwur Rana lived a secret life as a terrorist and helped facilitate the 2008 Mumbai massacre - in which 10 Pakistani gunmen stormed train stations, luxury hotels and a Jewish centre in India's largest city, killing more than 160 people.

The trial of the Pakistani-Canadian, who claims he was working for Pakistan's spy agency, the Inter-Services Intelligence Directorate, will be the first - and probably only - American legal proceeding to publicly probe the inner workings of the secretive service, whose reputation for nurturing terrorists instead of eliminating them was bolstered when agents failed to help U.S. counterparts find and kill Osama bin Laden.

The 50-year-old Mr. Rana is charged with conspiracy to provide material support to terrorism in the Mumbai attacks, and while he claims he is not guilty, he doesn't purport to be entirely innocent either.

"Defendant's proposed defence is that his alleged illegal acts of providing material support to terrorists - at least those related to the Mumbai attacks - were done at the behest of the Pakistani government and the ISI," reads one court document released this spring.

Colin Freeze

The Hasan Abdal Cadet College, located northwest of Islamabad, is a feeder school for Pakistan's military. Mr. Rana attended the school during the 1960s, when he studied to be an Army doctor.

He appears to be a Canadian of convenience. He got his citizenship during the late 1990s, precisely the time he set up a network of businesses in Chicago. He called his Illinois companies Bios Zabeeha Halal Foods and First World Immigration.

But Mr. Rana was allegedly lured into a different kind of enterprise as well. It was June, 2006, when a compatriot from the Pakistani boarding school turned up in Chicago to ask a favour.

Daood Gilani, the bicultural son of an American barmaid and Pakistani diplomat, arrived as the consummate chameleon. Light-skinned, and with one eye blue and the other brown, he had then just changed his name to David Headley.

It's anticipated that Mr. Headley, who has since turned FBI informant and pleaded guilty to avoid the death penalty, will tell the Chicago jurors that he told Mr. Rana he needed help with a "cover story." The goal? Help an ISI-sponsored terrorist group in Pakistan - Lashkar-e-Taiba - plot an attack on Mumbai.

"During my trip to Chicago, I told [Rana]about my meetings with … Lashkar. I also told him … how I had been asked to perform espionage work for ISI," Mr. Headley said in secret grand-jury testimony, according to court documents since made public. "I asked [Rana]if it was okay with him that I set up a First World Immigration office in Mumbai."

Mr. Headley spent the next few years travelling to India to scout out the eventual sites, supplying his footage to Pakistani handlers who gave him more than $25,000 for the job.

When the 2008 attacks did take place, some of the same handlers allegedly used the footage to coach the attackers - 10 young Pakistani gunmen with cellphone earpieces - through the massacre of civilians.

Helen Connolly, a Markham, Ont., yoga instructor who had gone on a meditation retreat, recalls hiding under a dining-room table at the Oberoi Hotel when the gunmen attacked.

She survived, but two close friends died. "We heard him shoot up all the other tables before he got to ours," she said in an interview. "I got the image of a teenager, a young man trying to earn a perfect score at a video game."

In the aftermath, U.S. officials rushed to reassure India there was no evidence the attacks were sponsored by Pakistan. President George W. Bush had ordered his officials to try to prevent an India-Pakistan war.

In private remarks, the head of the ISI appears to have been less categorical. "There may have been people associated with my organization who were associated with this," Lieutenant-General Ahmed Shuja Pasha told Washington officials, according to a 2010 book by journalist Bob Woodward.

The U.S. Federal Bureau of Investigation tried to play the role of an honest broker in the ensuing international criminal investigation. India's national-security adviser urged FBI director Robert Mueller to take a close look at the ISI.

"Pakistan's Inter-Services Intelligence Directorate was the root of India's terrorism problems," Mayankote Narayanan told the FBI, according to a leaked State Department memo that has surfaced on WikiLeaks. He advised that the "lower levels of the organization, who often support terrorist attacks without their superiors' knowledge, would also need to be addressed."

The alleged Chicago conspirators are said to have begun brainstorming new plots within weeks of the carnage. It's alleged that Mr. Rana and Mr. Headley settled on a plan to kill staff at a Denmark newspaper, one that famously published cartoons lampooning the Prophet Mohammed.

By then, the FBI had decided it was a good idea to monitor Mr. Rana's conversations. Court documents allege he was caught on tape talking to figures in Pakistan about how to exploit student-visa "loopholes." The FBI also says they overheard him reflecting on how a retired Pakistani military officer had tipped him to the Mumbai attacks - before they happened.

In October, 2009 - nearly a year after the massacre - Mr. Rana was arrested in Chicago and his empire unravelled. Hundreds of armed federal agents swarmed his rural Illinois slaughterhouse. FBI agents pulled computer hard drives from his immigration consultancy. Prosecutors say police retrieved al-Qaeda videos from his house.