I had a friend who worked at Theranos who has trouble finding work because he was there for 3 years.

The best engineer I knew at my last gig (a unicorn company we all use daily) worked at the major adult entertainment company for many years haha. Dude was a total family man by the time I met him and the nicest sharpest tech lead.

Complicated question. Also depends on the role, how close you were to the “bad” part, how specialized and in demand the skill is, etc. Generally the USG was in the business of hanging nazis or at least imprisoning them at the time, but operation paperclip brought a bunch of great scientists, and much more secretively the same thing happened to the arguably-worse Japanese war criminals.

I’d probably be fine with the guy handling ddos mitigation and keeping the site up for some random offensive racist or kitten-murdering website if it is just a technical challenge. Although there is also the negative PR impact from having hired such a person, since some people, including potential customers, would be less tolerant.

Hard problem. Anonymity or pseudonymous markets is probably the solution here.

The pay for gambling apps (in Australia, where it's legal) tends to be higher for precisely that reason. They'll often hide behind an unrelated name and refer to their industry as "gaming", too.