The famous WWII miscalculation is Chamberlain's doomed attempt to appease Germany, but far more fascinating is Janis's review of Japan's mistaken decision process leading up to Pearl Harbor (although America's equally foolish complacence played a part too.) It boils down to this. Democracies, accustomed to transparency and rational decision-making as it applies to a much wider chunk of their populations, assume that they're dealing in good faith with rational and above-board decision-makers whose citizens have access to full information. And this works fine when democracies are dealing with other democracies, but when they're dealing with dictatorships, taking statements at face value and assuming that being nice will be rewarded is a dicey proposition. Meanwhile, dictatorships can only assume that the so-called democracy of their enemies is just as much of a sham as their own "people's republic" (which people?), and that the leaders of those so-called democracies will sacrifice their population however they have to in order to preserve themselves. Hence Japan's misapprehension that the U.S. would fall back from Hawaii and sacrifice the islands to fortify more easily defended targets; this was after all the most rational decision from the perspective of just protecting the military. The Japanese command didn't realize that the American people were loyal to their government out of choice and that their demands to strike back had to be heeded by elected officials.
Bottom line: it's as if dictatorships are playing football and democracies are playing basketball. But this has been going on for long enough to have been studied, so we democracies can't act surprised anymore when a linebacker tackles us during a foul shot.
This is why there is growing concern in many quarters about the West's behavior toward China and North Korea. China recently made a point of collectively snubbing the rest of the world, and even prior to the Great Cyberattack the current administration was quietly pissed off about it. Looking at the recent tone in the Western press, it seems hopeful that China's Sudetenland days are numbered. Still, when you read things like this about China and its client states you can't help but worry:
Humanitarian aid [to North Korea], from Americans or others, is explained away as tribute from an inferior state or as reparations for past misdeeds. The 2008 visit of the New York Philharmonic to North Korea was depicted there as a gesture of respect for the regime. When former President Clinton went to the capital, Pyongyang, last summer to win the release of two detained American journalists, the official media made much of the deference and contrition that he supposedly showed to dictator Kim Jong Il.
Now China is asking, in arrogant tones, that NATO countries drop their arms embargo and start selling Western weapons technology to the People's Middle Kingdom again. It's time to call bullshit on China's perpetual victim card, and whether it's a Republican or Democrat who does it, we shouldn't care. At this point, it should be obvious that attempts to appease this prematurely arrogant dragon are futile. We can't make Chamberlain's mistake with China and North Korea; otherwise we're inviting them to make Tojo's with us.