There are 2 factors here. 1) If he's simply a mediocre IT jockey and then his NSA contractor status resulted in him pulling in $200+k a year, that's a bad look. 2) If he's average and he somehow managed to defeat the NSA at what the NSA does, that's also a bad look.

Now it's likely a policy problem, that contractors can access these quantities of data with access to physically removable media and such seems like a policy problem. On the other hand if he's some kind of computer super genius then he was given a little trust and took advantage of it.

It's less of a mouthful than, "practitioner of the dark arts and lay member of the Esoteric Order of Data-Gone".

Because 99% of the population have no idea how technology actually works.