Followup to: Unteachable Excellence
As previously observed, extraordinary successes tend to be considered extraordinary precisely because it is hard to teach (relative to the then-current level of understanding and systematization). On the other hand, famous failures are much more likely to contain lessons on what to avoid next time.
Books about epic screwups have constituted some of my more enlightening reading. Do you have any such books to recommend?
Please break up multiple recommendations into multiple comments, one book per comment, so they can be voted on and discussed separately. And please say at least a little about the book's subject and what sort of lesson you learned from it.
Albert Speer's autobiography, Inside the Third Reich.
Under Hitler's guidance, Speer pioneered the "ruin value" ideology in architecture - thus in a way focusing his trade on the question of how to fail with magnificence.
His attempts to build in a Berlin of the distant future an exponential replication of the ruins of the Roman empire was either never actualized or bulldozed by the allies. Today all that remains of his attempt to harness failure is a row of lampposts on a side street in Berlin.