He drank the kool aid and is now in full blown culture warrior mode.
Even if you think transphobic jokes are funny, he does them way too much and for too long and his comedy suffers for it.
He’s always been the king of terrible takes (how old is 15 really?), it’s just that he used to be skinny and have a higher pitched voice and yell the word “bitch” a lot, so he was sort of like a clown in a way. His stand up was always about race relations, and while the jokes were great back in the day, modern observations on current events mean you have to choose a side, and being an insanely rich gen xer, he chose conservative.