When Eastern District Judge Raymond Dearie (See Profile) gave a prison sentence to a member of a designated terrorist group that was less than half of what the government sought in 2012, he said it wasn’t easy.

“I will not miss this case because it’s given me some of the most difficult and, in many ways, loneliest moments of my career trying to figure out a rational, reasonable sentence,” Dearie said at the sentencing of Pratheepan Thavaraja of Sri Lanka, a member of the Liberation Tigers of Tamil Eelam.

Pratheepan was eligible for 20 years in prison but Dearie gave him nine years in a decision that was upheld Thursday by the U.S. Court of Appeals for the Second Circuit.

Pretheepan had pleaded guilty to buying more than $20 million worth of anti-aircraft guns, rocket launchers and other military-grade equipment in his role as a procurement officer for the Liberation Tigers, (LTTE), which has been designated a terrorist group.

He was charged with conspiracy to provide material support to foreign terrorist organization. Pratheepan had also pleaded guilty a conspiracy to bribe officials to take the LTTE off the State Department list.

The guidelines range was 30 years in prison, but statutory maximums on two counts put a ceiling of 20 years on the sentence. The Eastern District U.S. Attorney’s Office asked Dearie on Sept. 6, 2012 to sentence Pratheepan, then 37, to the maximum, in part because Pratheepan was directly involved in the procurement of suicide vests at a time of suicide attacks by the LTTE in its long-running war to break away from Sri Lanka and form an independent state.

But Dearie said compelling circumstances justified a significant downward departure from the sentencing guidelines range.

He said the case was unusual “because it carries the banner of terrorism and yet involves people who certainly pose no direct threat to the United States.”

At the same time, Dearie said “[w]e don’t justify the ends with this kind of means. Indeed, these folks, although they pose no direct threat, face severe sanctions here in the United States because we don’t in any way underwrite or care to underwrite terrorist activities anywhere in the world.”

He said Pratheepan had been a model prisoner for six years at the Metropolitan Detention Center, where he tutored other detainees and was not motivated by “power” or “self aggrandizement” but by a desire “to help the Tamil people,” adding “It is beyond me to make sense of the situation in Sri Lanka.”

Dearie, who said he consulted with fellow judges on the case, issued a follow-on opinion in October 2012 saying, “Despite his serious criminal conduct,” Pratheepan “is a person of substance and decency who was motivated solely to assist the Tamil minority in Sri Lanka who were engaged in an ongoing civil war that it now appears involved serious human rights violations on both sides of the conflict.”

The LTTE was formed in 1976 as a militant group aimed at creating a separate Tamil state. With an army of some 10,000 soldiers, it engaged the government of Sri Lanka in a civil war that included suicide bombings and assassinations and led the State Department to put the LTTE on the terror organization list in 1997.

A military offensive by the government ended the rebellion in 2009, three years after Pratheepan was indicted in the Eastern District.

On Thursday, in United States v. Pretheepan Thavaraja, 12-4330-cr, Judges John Walker (See Profile), Debra Ann Livingston (See Profile) and Denny Chin (See Profile) credited Dearie’s rationales and his broad discretion to downwardly depart, rejecting the government’s argument that the sentence was “substantively unreasonable.”

In their brief, Assistant U.S. Attorneys Alexander Solomon and Peter Norling argued Dearie had put too much weight on factors that appellate courts frown upon “such as whether the terrorist organization to which the defendant belongs poses a direct threat to the United States and whether the goals of that terrorist organization are not blameworthy.”

The prosecutors said the LTTE “is well know for pioneering the use of the suicide belt” and “is the only known terrorist organization to have assassinated two heads of state, Indian prime minister Rajiv Ghandi in 1991 and Sri Lankan president Ranasinghe Premadasa in 1993.”

But Chin, writing for the court, said Dearie’s sentence “fell within the range of permissible decisions.”

“The sentence here of 108 months was neither ‘shockingly low’ nor insupportable as a matter of law, nor would the administration of justice be damaged by allowing the sentence to stand,” he said.

Chin made reference to Dearie’s statement about the case presenting one of the “loneliest” moments of his career, saying “We can understand why, for many competing considerations came into play.”

While “Pratheepan’s crimes were certainly grave,” Chin said, “many mitigating circumstances were presented.”

Chin said Dearie did not err when he considered the degree of harm that an individual LTTE member “caused or intended to cause to the United States,” and while Dearie had noted the LTTE did not pose a direct threat to the United States, Chin said the district court “also made clear that it understood that individuals who violate our laws are subject to punishment here even if they are not a direct threat to the United States.”

Chin then rejected the prosecution’s claim that Dearie was weighing whether the goals of the LTTE were more or less blameworthy, saying “we do not believe this is a fair characterization of the district court’s consideration of the LTTE and its goals.”

“The district court was not opining that the LTTE was less ‘blameworthy’ than other terrorist organizations,” he said. “Instead, the district court was merely trying to understand Pratheepan’s motivations.”

“Pratheepan’s motivation was certainly relevant to the determination of his punishment, and it was appropriate for the district court to take his motivation into account.”

Michael Sporn argued for Pratheepan.