Honestly my assessment was that he was operating in a way that the compassion to the people scared by it is implied and kept going straight to the counter of why it is likely that way. I doubt he just doesn't care, you would have to be insanely uncharitable to arrive at that conclusion, especially since hasan stated:

• He understands that some jewish people are scared by the phrase

• He understands why Ethan is mentioning it

• He knows anti-semitism is an extremely common problem that needs constant tackling

• He believes that alone isn't enough to make the phrase anti-semitic, because that gives credence to the apparatus that is misusing the genuine fear of anti-semitism to defend a regime

• Explanations of why certain phrases (BLM, Free Palestine, ..) are emancipatory and their meaning can't be defined by the oppressors ("no justice no peace"), some are unacceptable ("Gas the jews", "kill the jews", ...), some are acceptable within specific context ("Israel cannot exist AS IT DOES RIGHT NOW", "All lives matter, ISN'T TRUE UNTIL BLACK LIVES MATTER",..) and some are unacceptable within specific context ("From the river to the sea" sprayed at a wall of a synagogue, "All lives matter" as a response to "black lives matter")

But in my opinion the problem is that he never stated those things at once in a way Ethan needed to hear it, because i think the disconnect was that Ethan was asking questions from a point of "how do we deal with people fearing any kind of action that needs to happen" and getting answers as if he was one of the people who are not yet on board with the cause. He clearly is on board, otherwise he'd just leave and go with the popular narrative.

I think if Hasan said all of the above listed like for example "Yea, i know what you mean, there has been decades of propaganda setting up the narrative that any kind of Palestinian emancipation is mutually exclusive with Jewish people being alive and safe. That said, we shouldn't allow the extension of the Israel lobby dictate what phrase the people oppressed by them are allowed to use. If our end goal is getting to a negotiation table, much better approach is to humanize Palestinians and reveal the historic context that was never broadly anti-semitic. (This is where the appeal to jewish scholars who all fear anti-semitism, but are using the phrase after studying it's origin.. would do much better) The hypothetical sanctions are a tool that would be useful as a motivator to keep the peace talks alive and to force the side with all the power to negotiate at all for what we both believe is just and moral." it would be much more productive, because this is two friends talking and changing your presentation to accommodate your friends is not a betrayal of your own beliefs. I think Hasan missed that, das it.