Trying to prevent programmers from doing something "because they may 'misuse' comments" is asinine to the extreme. This is not like removing a footgun, it's trying to dictate how you think programming should be done. This is particularly hilarious because I've instead seen tons of horribly hacky workarounds for JSON's lack of comments, e.g. "fake" object entries like "__previousKey_comment": "this is a comment for previous key", or even worse, putting two entries with the same key since the second key should "win", and thus making the first entry the comment.
As for his second point, "Suppose you are using JSON to keep configuration files, which you would like to annotate. Go ahead and insert all the comments you like. Then pipe it through JSMin before handing it to your JSON parser." - just look at the everlasting shit show that is package.json since it can't support comments, because lots of NPM tools actually write to package.json, so there is no guarantee that other tools will be able to read package.json if it includes comments.
I think the thing that I hate most about Crockford's rationalization of not having comments is that you have to have your head stuck 10 feet in the sand to pretend that somehow the lack of comments is a good thing with the benefit of hindsight. I guess I could understand if Crockford's position was "Yeah, originally I thought it was better to keep them out because I was concerned about misuse, but now in retrospect to see the much larger problems it causes, and I realize it was a mistake." But instead he just keeps pushing his original crappy opinion on this topic.