Not the sharpest knife in the drawer
"Police latched onto Monsegur, an unemployed 28-year-old from New York, after he made the mistake of logging into an IRC chat server used by LulzSec without using the Tor anonymisation service - and just days after LulzSec had attacked the Feds."
Monumentally stupid move. That's like having your KGB spies show up with KGB badges outside the FBI. Really, doing something like that is a surefire way to get the Feds knocking on your door!