I think this is the least problematic thing he has done to my knowledge

I mean, if he said it completely seriously, and the article was published saying he had, then he later came out and said "It was just a joke guys! Jeez, so uptight!", I'd agree with you, but it was apparently clear from the outset that it was a joke and the headline is likely intentionally written to sensationalize it. The only problem I see here is that someone at rawstory thought this was newsworthy.

Of all jokes from this crowd, this one I don't think is the kind that that's actually a hint.

That's "a" problem to be sure, but perhaps not "the" problem. For example, every president for the past 36 years has pardoned a turkey for thanksgiving. Given the genocide of Native Americans by the US government, and the supposed occasion of Thanksgiving this seems like many smacks in many faces. Or making light of execution, which America is just one of 3 OECD countries (us, japan, and south korea) who even have capital punishment anymore, is in extremely poor taste. So joking about free speech is tone deaf I agree, but not unprecedentedly so, and not necessarily the purview of either party.

Long story short, there are bigger fish to fry, and we can't afford to waste our anger rather than apply it where it belongs.