He found out that getting bad press is better than no press. Like the original thing that got him caught up in the headlines was crass but that's sort of his humor. This one, he's just being a gigantic penis about it and banking on the follow up outrage.
The thing is the anti-politically correct shtick only last so long. At some point it just becomes noise and then you have to up the ante which in turn alienates more people. Rise and repeat till it's difficult to get a booking anywhere but FoxNews.
Like much of anything. It's his career, far be it for me to tell him how to run it. But his comedy routine as of late has just turned resentful and aiming to get as many people to gasp "Oh my, he's such a bastard!" And in reality it just comes off as a big yawn.