If Bezos can't get $100M of losses worth from the Washington Post by other means, well, he's not using it very well.
However since he switched from the "Democracy dies in darkness" ethos to the "ah fuck it bring on the darkness, I own all the torches" ethos, he eliminated the possibility of him getting benefit from owning and running an elite institution in the information ecosystem.
It's been really funny to see a lot of tech execs fail to understand power, and its sources, when outside of their tiny section of the economy. Peter Thiel might actually understand a lot more, but Thiel seems to be the only one capable of doing anything except losing their power in an oligarchy.
"Buy a newspaper and smash it to bits while submitting to fascists" is bad, whether or not his investment is underwater. How much money has Bezos lost on the WP? I have a very small violin for him.
He may well have thought _he’d_ be able to turn it around —like buyers of perennially losing sports teams and then he figured out he was wrong. It happens without malice —if anything it’s seldom due to malice. People don’t like losing money.