> was it always this stupid?

Excellent question. There are two easily readable sources I know of covering historical events of the sort you're asking about. The first is Barbara W. Tuchman's The March of Folly: From Troy to Vietnam, where the entire premise is that stupid people did stupid things and then doubled down on stupidity as they went along. The second is Eichmann in Jerusalem: A Report on the Banality of Evil, in which Hannah Arendt details just how dull and unimaginative Eichmann was. She writes, "it was difficult indeed not to suspect that he was a clown", and suggests that Eichmann was not especially different from anyone he worked for, right up to the top.

History doesn't seem clownish because of the way it is recorded and taught. Even Arendt's writing is cool and formal compared to the histrionics we see on social media and many news outlets.

> Was there a Napeolonic era equivalent to a media figure known for making light of school shootings, getting killed in a school shooting, a second after again making light of school shootings?

The assassination of Archduke Franz Ferdinand, and subsequent events leading to the start of the First World War, were filled with errors and stupidity, so much that history mostly lumps them all under the term "July Crisis", and rarely goes into detail. If you're familiar with the Abilene paradox, you have a framework for how the Great War started as the result of collective actions by soldiers, diplomats, and national leaders.