A reader writes:
Sorry, but your reader cannot out-think Twain on the Philippines. One of Twain's more political, if less-widely-appreciated, writings was "To the Person Sitting in Darkness", a 1901 essay about the American occupation of the Philippines, in which we see the full venom of Twain's fury at colonial barbarism unleashed.
Gone is the gentle nudging of Twain's satire. Instead there is a brutally frank analysis of the geopolitics of colonialism, observed through the puzzled eyes of the "person sitting in darkness" (the liberated/colonized peoples), who wonder to themselves: "There must be two Americas: one that sets the captive free, and one that takes a once-captive's new freedom away from him, and picks a quarrel with him with nothing to found it on; then kills him to get his land."
Twain would not have been impressed with developments in education and health care 100 years after the fact, which would have been in his view accomplishments delayed by 50 years of the raw and direct use of the Philippines for American geopolitical ends. The latter was his real issue: the American role in "The Game", liberating economically-stagnant European colonies and incorporating them into a more vibrant American economy, can produce good or bad "development" outcomes, but never without the degradation and humiliation of subject peoples. Twain's argument is moral, not to be measured in future GDP:
There have been lies; yes, but they were told in a good cause. We have been treacherous; but that was only in order that real good might come out of apparent evil. True, we have crushed a deceived and confiding people; we have turned against the weak and the friendless who trusted us; we have stamped out a just and intelligent and well-ordered republic; we have stabbed an ally in the back and slapped the face of a guest; we have bought a Shadow from an enemy that hadn't it to sell; we have robbed a trusting friend of his land and his liberty; we have invited our clean young men to shoulder a discredited musket and do bandit's work under a flag which bandits have been accustomed to fear, not to follow; we have debauched America's honor and blackened her face before the world; but each detail was for the best. We know this.
There’s a big irony in your reader’s reading of A Connecticut Yankee in King Arthur’s Court. Twain was indeed writing about “the folly and hubris of trying to change a barbarous society,” but the society he had in mind was the American South. And while the folly and hubris of the eponymous Connecticut Yankee’s efforts are on display, I don’t think it’s correct to call the book a scathing indictment of them. The most scathing passages in the book depict the “chivalry” of a small minority that rests on the systematic enslavement of everyone else. These passages (and there are many of them) are simply dripping with outrage.
And this is not a small literary quibble. When people today talk of the futility and arrogance of trying to “reconstruct” a backwards society, they are echoing the words of those who abandoned the American South to the white supremacists in 1876.