There's nuance to be sure, but Chappelle's quotes aren't really very far out of context. He's been banging the anti-anti-anti-cancel-culture gong for years now, dancing constantly just shy of outright hate, deliberately. And this really was no different. The fact that he personally had a trans friend who was herself in a complicated relationship with the LGBT community[1] is interesting and notable. I'm not sure it's "context". Chapelle wasn't talking about Dorman in those quotes, and he certainly wasn't "mourning".

[1] And, again, "cancelled by the mob" is a pretty poor summary.