Dan and Tom can speak to this, but by my reading of the guidelines, "criticism of the current administration" and "views on topics like gender" are both explicitly prohibited:

"Please don't use Hacker News for political or ideological battle. It tramples curiosity." (https://news.ycombinator.com/newsguidelines.html)

It has nothing to do with being on the side of "the opposition" or "the man," it's because those sorts of posts inevitably lead to the same, repetitive, off-topic debates and flame wars.

Flagging should be used as a cudgel against posts that break the rules. There are plenty of places on the internet to debate politics and gender; HN is not one of them.

No, I'm talking about stories that are extremely relevant to hacker news and techies.

Which is attested to by Dan repeatedly manually unflagging these posts afterwards, which is an explicit approval that these posts follow guidelines.