I don’t think it’s the content of what he is saying that his supporters are drawn to. Trump has succeeded in positing himself as a victim of the “woke left” and the “establishment”. His entire project relies on this vehement opposition. He actually needs the political correctness because his opposition to it is what sustains him. There are theoretical studies of this, like for example Todd McGowan theory of left and right enjoyment. The enjoyment of the right is this enjoyment of transgression, the utterly childish thing of “I am gonna say exactly what you tell me not to say”. The more dumb shit he says the more it goes up. This is what some leftists do not get. You’ll never defeat Trump by showing that he said something bad and "transgressive ". This is exactly his appeal. The right succeeds in making a weird move. They cast the leftist as the “parent figure” that’s out there trying to steal your enjoyment. “You can’t say anything anymore these days”. Ironically the right is the moralizing position, but they succeeded in casting the left as this moralizing figure and we play right into their hands. The early leftist transgressive “hippy” figure has been replaced, in popular imagination, by the uptight professor telling you what you can and can’t say, and you saying it anyway and bonding with the class through that very prohibition.
I never claimed Trump never said stupid shit, but there are many instances where it’s so clickbaity which actually really helps Trump and his supporters. The appeal of Trump is that he posits himself as persecuted by the “woke mob” and “radical left”. He also depicted as someone “saying it as it is” and saying what the “establishment” doesn’t want you to say. There’s some theoretical work that studies how this happens, and I think many leftists rarely pose the hard question of why he is having a mass appeal. It’s not sufficient to just say “people bad and racist” and move on. The modern right succeeded in tricking everyone into seeing the left as this policing and hegemonic force out there trying to force you to say the right thing. It’s so ironic given that the right is the actual hegemonic and moralize force. The trick that they pulled is spectacular tbh and usually the left plays right into their hsnds. The fact that Trump says bad shit is not gonna harm him. That’s his entire appeal. It’s funny that leftist media thinks the more they show he said bad shit the more unlikely he’ll be supported. It’s the exact opposite. It’s the classic childish tragressive thing of “I am gonna say exactly what they want me not to say”. We are in the age of the “rebel punk” right, which is so fuckin ironic. Of course it’s not rebel or punk but they are formally in that positionz while the leftist is cast as the polished professor telling you what to say and what not to say. You can easily see the appeal of the right if you look at it this way, and see how this “trump said a bad thing” is exactly why he is popular.