My favorite kind of histories are those told from an insider's perspective. The story of Richard the Lionheart is full of great battles and dynastic intrigue. The story of one of his soldiers, not so much. Yet the soldiers' story, as someone who has experienced the real consequences of decisions made and actions taken, is more revealing.
We get such a history in Chat Wars, a wonderful article written by David Auerbach, who in 1998 worked at Microsoft on MSN Messenger Service, Microsoft’s instant messaging app (for a related story see The Rise and Fall of AIM, the Breakthrough AOL Never Wanted).
It's as if Herodotus visited Microsoft and wrote down his experiences. It has that same sort of conversational tone, insightful on-the-ground observations, and facts no outsider might ever believe.
Much of the article is a play-by-play account of the cat and mouse game David plays changing Messenger to track AOL's Instant Messenger protocol changes. AOL repeatedly tried to make it so Messenger could not interoperate with AIM and each time Messenger countered with changes of their own. AOL finally won the game with a radical and unexpected play. A great read for programmers.
For a general audience David's explanation of how and why Microsoft came to dominance and why they lost that dominance is most revealing. It stares directly into the heart of the entropy that brings everything down in the end.