Activist lawyers have their uses, but yes, very prone to confirmation bias, very prone to bask in their reputation for cleverness, and with a disturbing tendency to tell people what they want to hear.
Maybe I just don't have that element in my character, but I would think that, if there's a big case coming up and the group that you're advocating for is in a legally weak position, you have to be blunt with them.
So I've seen a few lawyers harrumphing about the SC ruling and I just want to say: Maaate. I know it's important to you to be a trans ally, but you must have known there was a reasonable chance ScotGov would lose this case. And you're familiar enough with transactivists to know there was a 100% chance of them throwing a massive tantrum if they didn't get 100% of what they wanted. You should have prepared your audience, but you didn't.