A very interesting read. I would say point 1 - catching up - is the biggest thing. Trump ended up being so much worse than predicted, to the point where he's effectively attempting a coup and people are so disillusioned by the past 4 years that they were predicting this would happen. That puts comedians in a completely different place than even with how awful GWB was, there was still the idea that he could be kicked out and no one has the tools to deal with it (though I disagree with you, I think Baron Cohen was the most successful which I may elaborate on at another time).

If I could elaborate on the Benign Violation Theory in terms specifically of the failure of satire in the Trump era, I would say one huge difference between now and previous eras is Trump clearly has narcissistic personality disorder. Even when say, GWB did something evil there was this idea that he thought of himself as a good man, or at least a human, and therefore that calling out his evil or his hypocrisy lended a value greater than just catharsis even if ultimately that's all it ever achieved.

However, Trump doesn't think of himself as a good man, or even a human, but as God. He doesn't do things because they're right, things are right because *he* does them. He will never ever ever listen or grow or change or feel remorse, not out of choice but because he is clinically incapable. This adds a greater level of futility to satirising Trump, and if the act is futile, then no one will ever feel violated AND safe at the same time, just violated.

I think it's interesting to contrast this with the strand of "satire" that did become popular during this era, which is the John Oliver Last Week Tonight style. I would hesitate to even call it satire, I think of it as info-ainment, and I don't mean that as a criticism despite the connotations of the term. It's an incredible, boundary pushing version of infotainment, but it's not satire. LWT breaksdown a specific, complex issue into something that you can understand, in an entertaining way, and at its best goes "here is why this is bad" (violation) "and here is how it can be fixed" (safety). It's a balm to futility, and if satirising Trump is a futile act, then that explains the rise of John Oliver style "infotainment" as opposed to a re-invigoration of Jon Stewart style satire.