There's so much that's skewed here it's hard to know where to begin. First off, the academy is not separate from society any more than law is separate from politics, but each is a subset with its own prerogatives. Those serve a function and should be respected, but they're not Platonic absolutes.
In re: John Yoo. Though I seem to be the only one so far to bring this up, a lawyer outside the academy and in public life is a licensed professional. An engineer who builds a bridge that collapses under its own weight will lose his job. Historians and professors of comparative literature, even of jurisprudence, don't run that risk. Street lawyers do.

It would also be good to remember that academic freedom is not freedom of thought, it's freedom of thought for those who've been accepted into a club. To think that this exclusivity is a good idea is not to think it justifies excess self-importance.
"Academic freedom predates free speech."
"After all, even the King..." I wouldn't call that something to be proud of in a democracy.

2 decades ago as a 21 year old I read Gravity's Rainbow and a fragment of it became a touchstone of my intellectual life. It's the parallel description of two acts of self-destruction: the mass suicide of the Herero in Südwest as a last act of refusal and denial of the authority of their masters, and the same act by the Schwarzkommando as the an act of purest nihilism. Preempting claims of what geeks call Godwin's Law, the significance of my memories does not concern Naziism but values and context. Academic freedom historically has been tied to general freedom of thought and to democracy, but now it's linked to institutional privilege and defended with references to monarchy. I support it though preferring to think of it as "academic independence" but I would strongly suggest that academic specialists stop pretending their shit don't stink.

The classic defense of the free market is that its openness and vulgarity act as an astringent, testing and tightening thought what would otherwise risk becoming arid blather. But now that the market has reached the academy it wants to escape its roots. So we have an academy predicated not on the hopes of the humanities and of democracy but on the technocratic logic of reactionary schoolmen. Welcome to the 14th century.

First and foremost Yoo was and is jobbing lawyer. Lets see what his fellow tradesmen say.