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.