Chappelle has built a career making these kinds of jokes.
His 2019 Netflix special, Sticks and Stones was criticised for "punching down" at women, LGBTQ+ people and survivors of sexual abuse. He also has a history of making jokes at the expense of gay and trans people.
In 2016 while hosting SNL, Chapelle said he was willing to "give [Trump] a chance" during his presidency, although he did concede that "America's elected an internet troll".
He appeared to recant this comment and began to address allegations of transphobia during a comedy show the following year. He read out a letter from a trans fan to an audience in Washington DC, but stopped short at actually apologising for his words.
From Chappelle's more recent work, though, it appears that he's unwilling to move on from trying to shock audiences and generate controversy.
@theejayy i thought that one of the things dave said after his show is that he realized that he was being socially… https://t.co/nsAANudqPt