On Thursday, David Coleman Headley was sentenced to 35 years for his part in the deadly 2008 Mumbai terror attacks.
"I don't have any faith in Mr. Headley when he says he's a changed person and believes in the American way of life," said U.S. District Judge Harry Leinenweber in imposing the sentence, which was in the range of what prosecutors had requested for Headley's widespread cooperation.
Federal prosecutors in Chicago asked that Headley, 52, be sentenced to 30-35 years in prison, a merciful punishment considering he faces a maximum life prison term. Authorities said that Headley cooperated from the moment he was arrested, resulting in the criminal indictments of seven other terrorists.
Headley pleaded guilty to scouting locations for the 2008 attack on Mumbai, India by Pakistani terrorist commandoes. It was Headley's video travelogue provided to terrorist leaders that pinpointed the targets of a three day siege on the city.
"Despicable doesn't begin to capture the horror, the nightmare, I don't have the words to describe the pain and suffering inflicted upon the people of Mumbai, on the citizens of India and the citizens of the US and all the others who were killed and injured and the horror that must have been felt by the people in Copenhagen when they learned about the plot," acting U.S. Attorney Gary Shapiro said.
Even though Headley pleaded guilty in a deal with prosecutors, his own attorneys said that even a 30-35 sentence for Headley is excessive considering his cooperation.
"Mr. Headley's letter to the judge expressed his sincere remorse. It was voluminous and it was very clear and he did explain in that letter what led him to this and how sorry he was and we'll leave it at that," one of Headley's attorneys, Robert Seeder, said.
Headley's sentencing brought out former U.S. Attorney Pat Fitzgerald who supervised the origins of the case.
Fitzgerald was a witness for both the prosecution and defense, describing Headley's horrific crimes and his quick, thorough cooperation.
To move more freely through India, Headley changed his name from Daood Gilani. But as with his one blue eye and one brown one, Headley was study in contrasts. Criminal contrasts.
The lanky Headley has admitted using his American appearance to move freely through India, scouting attack locations for Pakistani terrorists who later executed a deadly 2008 siege on Mumbai. It was a three-day rampage in which 10 militant-gunmen fanned out across the city, attacking a crowded train station, the landmark Taj Mahal Hotel and other targets. More than 160 people were killed, including children.
Headley seemed to leap at the chance to spill secrets following his 2009 arrest by the FBI in Chicago and continued providing details even after the U.S. government agreed not to seek the death penalty or allow extradition in exchange for his cooperation.
"I and victims' families think he should spend the life in prison," said James Kreindler, an attorney for relatives of American victims. "Thirty-five years will upset some people ... but if that sentence means you got good information out of him ... and he gets out with a few years to live, some can tolerate it."
Prosecutors say Headley was motivated in part by his hatred of India going back to his childhood. He never pulled a trigger in the attack that's been called India's 9/11, but his contribution to the Pakistani-based militant group, Lashkar-e-Taiba, made the assault more deadly. He conducted meticulous recon missions - videotaping and mapping targets - so the attackers who had never been to Mumbai adeptly found their way around.
"What he did was unfathomable," Kreindler said. "Imagine what is going through a person's mind who is videotaping these places knowing what will happen there later."
Prosecutors also praise Headley for testifying against Tahawwur Rana, a Chicago businessman convicted of providing aid to Lashkar and backing a failed plot to attack a Danish newspaper for publishing depictions of the Prophet Muhammad. Rana, sentenced last week to 14 years in prison, claimed his friend Headley duped him.
Testifying at Rana's trial, Headley spoke in a monotone voice, seemingly detached, even as he described one proposal for the never-carried-out Danish plot to behead newspaper staff and throw their heads onto a street.
In video excerpts of his interviews with the FBI after his arrest, Headley appears flippant, cool and calculating. As he revealed Rana's name, he told an investigator in an upbeat voice, "That probably is going to be good a plus for me. Also for you."
Headley has become the face of terrorism in India and is a reviled figure. Thursday's sentencing in Chicago is being watched closely there and a sentence less than those routinely meted out to convicted drug traffickers or child pornographers is likely to draw outrage.
Prosecutors seemed to anticipate that in their filing, acknowledging that, "Determining the appropriate sentence for David Headley requires consideration of uniquely aggravating and uniquely mitigating factors."
Prosecutors have recounted only in broad terms how Headley has shed light on the leadership, structure and possible targets of Lashkar-e-Taiba, which was believed to have ties to the Pakistani intelligence agency known as ISI. Headley has said his ISI contact was a "Major Iqbal," who was named in the indictment that charged Headley.
Seth Jones, a RAND Corp. political scientist, agrees Headley must have provided useful insight for American intelligence, especially about how Pakistani intelligence agents allegedly reach out to people like Headley.
"From my perspective, this was pretty detailed information about one ISI contact (Headley) with one handler, Iqbal," said Jones. But he added Pakistani intelligence would have been careful not to reveal too much to Headley, saying, "They didn't trust him either."
For his cooperation and guilty plea to 12 counts, Headley secured both a promise that he would not face the death penalty and would not be extradited to India. Late last year, India secretly hanged the lone gunman who survived the Mumbai attack, Mohammed Ajmal Kasab.
The 12 counts Headley pleaded guilty to included conspiracy to commit murder in India and aiding and abetting in the murder of six Americans, who included Americans Alan Scherr and his 13-year-old daughter, Naomi.
One survivor, Andreina Varagona, described in a presentencing filing dining with the Scherrs at a restaurant when gunmen burst in. Bullets tore apart the room as they dove under a table, the girl screaming.
"I suddenly felt the warm spray of blood on my face and in my hair. ... Naomi's screams had stopped too, and I saw her lying lifeless beside (her father)," she recounted. "They'd both been shot dead."
The Associated Press contributed to this report.