This isn't a big change really. He's always said he's a lefty. If anything I think he's gone a little too far trying to draw a right-wing audience (although it's a good business decision to target the audience with the least competition). He's stated he dislikes Trump numerous times in the past, and he's entitled to his own opinion. What makes him easy to listen to, is that he doesn't fixate on Trump to the point of making a display of mental derangement. From time to time he'll make a statement and move on. And he'll even call people out for making ridiculous excuses to attack Trump. I don't see him developing a full blown case of TDS any time soon (he'll keep as much of his audience for as long as he can).