I do see the appeal in defending the indefensible, or at least those with indefensible views. I think it comes from trying to see the good in everyone, or at least the morally grey that we all fall under. You likely know someone with similar reprehensible views, especially if you live in America, and people project those attacks onto them. As for why the defense doesn't go both ways, the illusion that the other side holds all the cards and has a stranglehold on all industries is what leads their defense to not be equal across the board, and the logic "why would you defend something that's so obviously right" becomes the most prominent rationalization. I've seen that exact defense used before from some of these e-celebs; "everyone else is already doing it, so I don't need to throw my hat in that ring". Or people use that one quote that I always forget about the need to defend unpopular speech precisely because the popular speech is already self-evident or something.
I have a very conservative brother-in-law. He voted for Trump, thinks the stuff with Roy Moore is fake news, is pro-life, believes homosexuality is a choice, refuses to wear a Kippah when we have Passover, and probably a few other views I don't know. He's also incredibly nice, loves his dog, has never been anything but polite to everyone I've seen him talk to regardless of race, political views, sexual orientation or even gender identity, donates to good causes, and best of all brought my sister out of a crippling depression. People aren't black and white; they aren't super villains happily clapping their hands as the rights of minorities are taken away and they aren't saints that can do no wrong.
I extend that belief to people that have fallen in with bad crowds. I hate to bring up Gamergate, but that thread about Witchfire got me thinking about another figure in it; American Mcgee. How can someone who was for inclusivity in the industry and his own games, as well as someone whose sister got kidnapped and probably killed (so he should be able to empathize), align himself with a harassment campaign? Does he not know? Are his priorities just out of whack? Does he just not like Anita? I remember he once wrote a whole post on Facebook mentioning his alignment, but he didn't say anything about the harassment or the figures that were on the side of the harassed; he just spoke about censorship and his discomfort with it after describing his experience making the first Alice game and the reluctance of certain voices being credited because of what the game entailed, and IIRC the troubles of it even getting published because of the subject matter. Maybe other people in the movement are just like him; not believing in the full mission statement of harassment and pushing women/minorities out of gaming and just latching on to one aspect. That obviously doesn't excuse them, but I feel it makes things more understandable for some of them at least.
Which brings me to my next point. It seems impossible to be a free speech absolutist without either aligning yourself with or being a useful idiot for some despicable people. I've been called a Nazi on twitter for defending the rights of those despicable people. I'm Jewish; I know what the Nazis did. My great aunt had a front row seat to Mengele's horror show as he sewed infant twins together without anesthesia. And yes, I know background doesn't prevent you from falling in with that crowd as Milo did, but I'm not like that. I'm just someone that greatly aligns with the ACLU when it comes to free speech. It's the same with my discomfort around "bash the fash" as a widespread thing even if I'll never feel bad for the individuals that get punched.
It's just been tough for me to navigate the current political landscape even beyond interpersonal relations. A big part of my identity is my sense of humor which is somewhat edgy, but it seems like having an edgy sense of humor and being progressive is incompatible these days. When gay marriage became legal, it was one of the most exciting days of my life. My cousin proposed to his fiance in Manhattan
with a flash mob that we were all part of as the backdrop. It ended up being the best wedding I ever went to. And I've fought for progressive causes beyond just that, even if I certainly could have done more. And yet I've been called a garbage person on this very site for looking back at my time as part of the communities on Newgrounds and 4chan with fond nostalgia. Am I part of the problem if I continue to enjoy these edgy people by giving them views? Do I need to recreate my identity from scratch with a new, more subdued sense of humor? Do I even have the strength to do that when I already get such little enjoyment out of life in general?
So yeah, that was longer that I expected it to be, but maybe Boogie has a similar mindset with his constant fence-sitting?