NGL, if you can’t have a face to face conversation with them multiple times, you’re probably not going to be successful. You can’t really out theory someone online bc it often just turns into debatelord shit (even if that’s not your intention.) this is especially true with TERFs because they can be very cult-like. There’s a good chance that if you find the theory you want, they’re gonna take that theory to some TERF community and a bunch of people are gonna reverse-engineer some objection to it.
the problem is, if someone is a leftist and they can’t see the obvious reality that anti-trans bigotry is a tool the ruling class uses to divide and conquer, and they’re willing to live in a country where trans kids are literally committing suicide and/or being bullied by their classmates and the state, they’re kinda a lost cause at that point. I’m nonbinary, there’s a group of people who just refuse to see me as a human being, nothing I’m gonna say is gonna convince them to.
You might be able to come at them from a practical perspective that anti-trans bigotry makes them less effective as an organizer because it turns them into a wrecker.
I’m not saying this is impossible because I don’t know you or know them, but you gotta be really prepared for this to fail before you go into it. What you’re doing is admirable! I’m not being a naysayer, but a lot of legit TERFs often end up in that place because other TERFs weaponized some kind of trauma against them to make them think that way. For example, look at Dave Chappelle. Though he’s not a legit TERF, it’s been speculated that part of the reason he took the transphobic path was out of a real and valid anger at how white queer people weaponize racism against Black men while still claiming the oppressed class status. I don’t think that justifies hating trans people but it is a valid criticism since many white trans people are still fine being racist (see: lib trans people supporting Israel)
the real issue is the claim that trans is bourgeois decadence. someone spouting that nonsense doesn’t know anything about trans people. most of us are poor! most trans people live in the Global South. if someone ends up taking that position, they’re just completely out of pocket to the point where they might not be reachable.
probably because he’s also a rich person and he’s been living in a rich person comedy bubble for decades at this point. He’s had an elitist rich person streak to him for a log time, just look at how poor Black people were treated on Chappelle’s Show.