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Tahawwur Rana, middle, was cleared of any involvement in the deadly 2008 siege of Mumbai but was convicted of lesser charges of supporting the group that took responsibility for those attacks.

A Canadian citizen was sentenced to 14 years in prison Thursday for lending support to the terrorist schemes of David Headley, the Pakistani-American operative who will be sentenced himself later this month for plotting the mass murder known as the 2008 Mumbai massacre.

"This serious prison sentence should go a long way towards convincing would-be terrorists that they can't hide behind the scenes, lend support to the violent aims of terrorist organizations, and escape detection and punishment," said Gary Shapiro, acting U.S. Attorney for the Northern District of Illinois, according to a news release.

He said that Tahawwur Rana "provided critical support to David Headley and other terrorists from his base in the United States, knowing they were plotting attacks overseas."

The tandem of Mr. Headley and immigration consultant Mr. Rana was first explored at a sensational trial in Chicago two years ago, where evidence revealed how the boyhood friends from Pakistan grew up to become North American-based operatives for the Lashkar-e-Taiba (LeT) Islamist guerilla group.

Mr. Rana, a Pakistan-born Canadian citizen who ran an immigration consultancy in Illinois, had faced up to 30 years in prison. He provided cover stories for and travel documents to Mr. Headley, a chameleon of a man who frequently crossed borders while scheming violence on an epic scale.

When arrested in Chicago in 2009 by Federal Bureau of Investigation agents, both men stood accused of helping LeT scout out the targets in India before the attacks where, over three days in November, 2008 , LeT-trained gunmen shot dead nearly 200 people in India's largest city.

The FBI further accused both men of plotting a distinct but never-realized scheme to follow up Mumbai, one which involved tasking gunmen to storm a Copenhagen newspaper that had lampooned the Prophet Mohammed.

Evidence aired during trial showed the two suspects had become acquainted with loose network of shadowy intelligence, military and terrorist figures in Pakistan who helped to try to turn these conspiracies into reality.

Mr. Rana, 52, beat the U.S. charges that he helped plan the Mumbai Massacre. Yet he was convicted and sentenced for knowingly lending support to Mr. Headley, LeT and the Denmark plot.

The Canadian citizen had a heart attack in a Chicago prison last year. His lawyers had pleaded for clemency, arguing he is a very ill man who amounts to a peripheral and largely unwitting player.

A defence brief filed this month portrays Mr. Rana as a successful immigrant, a loving father, and a "compulsive entrepreneur" whose downfall came only out of a misguided desire to help a friend.

"Emigrating first to Canada, Rana eventually settled in the United States, a country he loves to this day," reads the submission. "... But for his friendship with David Headley, Rana would never have been so much as suspected of involvement in any sort of violent activity, let alone face sentencing following a conviction for providing material support" for terrorism.

Whether that's true or not, Mr. Headley is by far the more culpable figure. Following his arrest, he turned FBI witness to give testimony against Mr. Rana, speaking nonchalantly at trial about how they plotted the deaths of scores of people.

Mr. Headley cooperated in hopes of escaping the U.S. death penalty. He is to be sentenced on Jan. 24.

The son of a Pakistani diplomat and American woman who owned a Philadelphia bar called the Khyber Pass, Mr. Headley was raised in both countries. He grew up to become a lawless globetrotter whose allegiances were ever in flux.

Convicted of dealing drugs in New York in the 1980s, he became a U.S. Drug Enforcement Administration agent who spied on Pakistan trafficking networks during the 1990s. During the 2000s, he fell in with LeT figures in Pakistan, who trained him to be a terrorist bent on attacking India.

The chameleon retained one true friend in his life – Mr. Rana, whom he met as a boy at a Pakistani military-boarding school before the two got reacquainted as adults in the United States.

In months and years leading up to the Mumbai massacre, Mr. Headley – born "Daood Gilani" – meticulously planned. He officially adopted an Anglicized name and also prevailed upon Mr. Rana for false credentials from his Chicago immigration consultancy. The hope was that this name and cover story would better afford Mr. Headley opportunities to scope out luxury hotels, trains stations and a synagogue in Mumbai, without anyone asking questions about his Pakistani heritage.

Mr. Headley testified that he brought videotaped reconnaissance of the eventual targets back to his LeT handlers in Pakistan, and that the attack's masterminds used the footage to train the gunmen who would rampage through Mumbai.

When the gunmen did arrive, they came by boat to the city's harbour before shooting dead scores of civilians, as they were given tactical telephone instructions by commanders in Pakistan who watched the carnage transpire live on 24-hour news television.

After the massacre, the FBI sought wiretaps against Mr. Headley and Mr. Rana for reasons that remain unclear. Before long, the two men were caught discussing a scheme to have gunmen besiege the Copenhagen offices of the Jyllands Posten newspaper.

This plot was apparently supported by an al-Qaeda figure named Illyas Kashmiri in Pakistan who pledged to lend men and materiel to the cause. The common hope was that the attack would avenge the honour of the Seventh Century Prophet Mohammed, whose caricature in that newspaper had by then already inspired a terrorist bombing against a Danish embassy Prosecutors are seeking two consecutive 15-year sentences for Mr. Rana.

"The evidence demonstrated that the defendant knew that he was assisting a terrorist organization and murderers, knew their violent goals, and readily agreed to play an essential role in achieving their aims," reads a U.S. Department of Justice sentencing submission.

At trial, prosecutors introduced wiretap evidence revealing that Mr. Rana had expressed hopes that the shooting of Danish citizens "would be a huge event in the media" and that he had also praised the Mumbai Massacre after the fact as an event that had struck "fear in the hearts of Indians."

The sentencing submissions reveal a previously unheralded piece of evidence – Mr. Rana's wife was also caught on wiretaps prior to the arrests. She was allegedly overheard by the FBI as she griped about how her husband had fallen under his boyhood friend's spell.

"[Headley] is absolutely crazy. . . . Both [Rana and Headley] are alike [and] have ended up together. They talk nonsense all day, idiots," she said, according to prosecution brief.

According to the filings, she was overheard saying the men would say things "such as, 'kill him, he is not practising like us – kill him, do that to him, do this to him' … She is said to have asked rhetorically: "Is this how Islam spreads? ... Hatred spreads like this, not Islam."

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