In this May 23, 2011, file courtroom sketch, David Coleman Headley is shown in federal court in Chicago. Headley, who was convicted of charges related to a central role he played in the 2008 terrorist attacks in Mumbai, India, was sentenced Thursday. (Tom Gianni/Associated Press)

A federal judge imposed a 35-year prison sentence Thursday on David Coleman Headley for his role in plotting the 2008 Mumbai terrorist attacks that killed 166 people, including six Americans, and for a foiled plot in Denmark.

Headley, a 52-year-old businessman and former U.S. drug informant, avoided the death penalty by confessing that he conducted surveillance for both plots and cooperating extensively with investigators after his arrest in October 2009.

He had revealed startling
evidence that Pakistan’s Inter-
Services Intelligence Directorate (ISI) played a central role with the Lashkar-i-Taiba militant group in the attacks. His testimony enabled U.S. prosecutors to charge Lashkar members and a serving major in the ISI.

As a result, former U.S. attorney Patrick Fitzgerald of Chicago — who negotiated Headley’s plea bargain with him and is now in private practice — took the unusual step Thursday of appearing in the courtroom to ask the judge for a sentence of 30 to 35 years rather than life.

Nonetheless, U.S. District Judge Harry Leinenweber made his distaste for Headley clear. In addition to citing the horrific nature of the three-day slaughter in Mumbai, the judge pointed out that Headley had received two generous plea bargains from prosecutors when he had been charged with heroin trafficking in the 1980 and 1990s.

“I don’t have any faith in Mr. Headley when he says he’s a changed person,” Leinenweber said. “I hope the sentence I impose will keep him under lock and key for the rest of his natural life.”

Headley must serve at least 85 percent of the sentence, which means he may not be released until he is in his late 70s at the earliest. Nonetheless, the government’s treatment of Headley has stirred criticism from victims of Mumbai, the Indian public and attorneys for an accomplice, Tahawwur Rana, who was sentenced to 14 years last week.

Those sentiments were summed up in a vivid, emotional statement in the courtroom by Linda Ragsdale, an American who suffered severe gunshot wounds when gunmen burst into the Oberoi Trident hotel in Mumbai as she was dining, unleashing a fusillade with AK-47 assault rifles and grenades.

Ragsdale wept as she described hiding under a table with a 58-year-old father and his 13-year-old daughter, Alan and Naomi Scherr of Virginia, and seeing them both die.

She then read a brief statement from Kia Scherr, the wife and mother of the victims. “It would be an appalling dishonor if he only gets 35 years,” Scherr said in the statement. “It would not do justice for this crime.”

Headley, a tall, balding Pakistani American who wore a gray sweatsuit in court, did not make a statement. Western and Indian investigators consider him a uniquely skilled and dangerous terrorist because he received training and direction from the Pakistani spy agency as well as Lashkar and al-Qaeda.

He used his charm, language skills and American passport to conduct meticulous undercover reconnaissance in India, Denmark and elsewhere. Investigators say his scouting — along with funding, planning and expertise provided by the ISI — was crucial to the success of the Mumbai attacks, one of the most devastating and sophisticated plots since Sept. 11, 2001.

Headley’s handlers have been identified as a Maj. Iqbal of the ISI and Sajid Mir, a veteran Lashkar chief accused of designing the attack. Iqbal remains an officer in the Pakistani security forces, and Mir remains in Pakistan protected by the ISI, U.S. and Indian counterterrorism officials say.

Asked Thursday whether Pakistan has made any effort to arrest the accused masterminds, Gary Shapiro, acting U.S. attorney in the Northern District of Illinois, said, “I have no idea.”

A U.S. counterterrorism official, who is familiar with the case and who spoke on the condition of anonymity, said this week, “No one is looking for them in Pakistan.”

Headley’s sentencing did not answer questions that have dogged the U.S. government.

Authorities have not explained why the FBI and other agencies did not respond more aggressively to six warnings from Headley’s wives and associates about his terrorist activities between 2001 and 2008.

Moreover, the FBI, Drug Enforcement Administration and other agencies have not explained the extent of Headley’s work as an anti-drug informant, especially in 2001 when he began gathering intelligence on Islamic extremists as well as drug traffickers.

Finally, authorities have not explained why it took almost a year to arrest Headley after the Mumbai attacks, even after a tip led agents to discover that he had been the subject of repeated previous allegations of involvement in terrorism.

Headley’s attorneys had asked for a lower sentence than 30 to 35 years, asserting that their client’s “unprecedented” cooperation had “saved lives” around the world and that he had expressed remorse.