So here’s the Monday morning story you’re all going to be talking about: The New York Times goes deep on the background of Private Bradley Manning, the Baghdad-based Army intelligence specialist suspected of passing all that data to WikiLeaks.

It’s an emotional, fascinating read. But the story doesn’t answer the one question that a lot of military people — and yours truly — really want answered. Crispin Burke, editor of the outstanding blog Wings Over Iraq, tweets the question thusly:

“Tons of money spent on Top-Secret clearance investigations, and they’re granted to emotional train wrecks?”

He’s got a point. The single-scope background investigation for a top-secret clearance is pretty exhaustive; beyond the expected secret-squirrel games, they talk to your friends, family, landlords, and teachers…then they talk to the friends of your friends, family, landlords, and teachers. NYT indicates that Manning was pretty openly gay, emotionally frustrated and combative (I sympathize with that one), and the young son of divorced parents, one of whom was Welsh (and took him to complete his secondary education in the UK). Also, he was fired once from a civilian job because of personality issues, and he got two reprimands — Article 15′s, in Army-speak — for misconduct, including “assaulting an officer.”

Now, in recent years, one of the biggest problems in the US’s clandestine and sensitive-data services has been the terrible homogeneity — the whitebreadiness — of its personnel. After 9/11, we were behind the eight-ball in terms of having out-of-the-box thinkers and world travelers who were cleared to gather and analyze our most protected information. But it’s hard to imagine that even the most liberal of background clearances wouldn’t have thrown a couple of red flags up when investigating a kid like Manning.

None of this is to say that Manning’s background was “flawed” or he was any less of a fully-functioning American kid because of his tough family upbringing and sexual orientation. But it doesn’t sound like the military life was fundamentally for him (and I feel qualified to say this; it takes a reluctant ex-service member to know one).

Bottom line: Did Army security investigators screw the pooch on this one?