“I remember one day we tricked two dumb high-school girls from town into the fraternity house and made them put out for all the fellows there ...

https://en.m.wikipedia.org/wiki/Captain_Aardvark

I read Catch-22 in high school, and that bit felt plenty disturbing at the time.

Are you suggesting you’d have been better off if they had banned it?

This is likely why: https://en.wikipedia.org/wiki/Catch-22#Anti-capitalism

I mean, really there's a lot in there that the people banning these books would probably find offensive. Questioning the MIC, questioning God, questioning capitalism...

That's wild, I took almost the opposite message from that scene. Since the bombing run is seen as inevitable Milo engineers the situation to guarantee a minimum of actual damage is done in order to protect his profits.