I think he may have, as The Coming Anarchy and his books about Africa all deal extensively with the history of the country in question (usually going back centuries), talks quite a lot about the impact of colonialism and occupation on them. He spends major amounts of time in his books talking with regular people. In Africa he walked around shantytowns talking to people, and took regular buses, declining embassy cars, rides that were stopped on a regular basis for shakedowns by whatever militia/army was controlling that street that day. He seems quite able to value what a Kurdish herder told him as well as dismissing some ambassador types as idiots.
He's also written a book about his travels through the U.S., "An Empire Wilderness", which is hardly cheery about where we are going. Parts of it focus on the underclass, and other parts are critical of massive "redevelopment" plans in cities which dislocate and hurt the working class and poor.
He mentioned in The Coming Anarchy that he had been a relentless cold warrior, but, it appears his views have changed, as much of his books now detail how power politics played by the big powers have wreaked havoc on smaller countries, how all the rules are changing, and how, if for no other reason than self-interest, the West/U.S. needs to realize that what happens to these countries affects them directly.