Maybe he shouldn’t have agreed to take the picture but he didn’t write the caption. They’re clearly using him for a political stunt.

Are they though? He’s been pretty openly transphobic.

How so? Maybe I’m uninformed

His last few specials were controversial for their takes on trans women. And he seems to be really hung up on the topic.

Any links to the relevant clips, or episodes? I don’t really watch Chappelle.

Anything from his special The Closer that involves trans people should work. I didn't say jokes, because he just kind of rants about it and doesn't seem to be making any actual jokes.