Update: Sowell video was monetized. Still hope to hear from @teamyoutube what caused the demonetization in the first place and what “context around the video” means. That’s a new piece of the puzzle...https://twitter.com/rubinreport/status/987401513348845571 …
I think you can get a hint from what's happening on campuses. The reality inside YT is probably that management is as terrified of its employees, as admins are of students. So they just let opinionated employees (who would gravitate to such jobs) make decision without oversight.