In my mind this parallels Obama and the healthcare.gov problems. In both cases the leader may have done all the usual "due diligence", but in both cases there was* no appreciation for Murphy's law, for the black swan event. And in both cases the bad happened, and it was bad.
In an ideal world the leader would do a stress test on his bureaucracy, worrying about contingency plans. You recall Eisenhower had at least a contingency message prepared in case D-Day was a fiasco and the troops had to be evacuated.
* I write this knowing there's been no real reporting on the decision process in either case, at least no tick-tock book which I've read.
I'd also note that Trump's agreement with the Taliban put Biden in a tough position. My knee-jerk reaction is that he perhaps should have kept the troops and support going until the last minute while paring down the civilian contingent and especially getting all the interpreters and otherwise vulnerable people on the way out of the country.
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