I have mixed feelings about this. Colin is an exceptionally bright guy. In find him quite impressive intellectually. But you're right that I don't think he'd done much analysis of insurgency until a few years ago. But what does qualify someone to be an "expert"? After, the military suffers from what I've heard called the "any colonel can" syndrome--the idea that if someone was competent enough to become a colonel, he can do any job. So we end up with colonels and generals with no counterinsurgency background leading counterinsurgency efforts.
I've also been concerned that in terms of counterinsurgency, TOO MUCH expertise can be an impediment. As the U.S. military has re-engaged with it, I've heard a lot of people with deep experience go to great lengths to cram Iraq into the box of El Salvador or even Vietnam. Sometimes it takes someone without deep experience to think creatively.
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