First appearance was episode 163. I remember because ironically that was the first full episode I listened to. He called in to talk about his vaping Belle Delphine bathwater video which got popular at the time (tbf it was a troll that people fell for, but even at the time everyone who saw it clowned on him for being a fat hideous freak). Because they both live in LA, he started coming in studio and became the third mic to replace Asterios who had stopped showing up after he wanted to go forward with his countersuit. I think they rebooted Biggest Problem in 2021; Dick had talked about reviving it after winning the trademark outright in 2019 and threw it around to a couple of people (he talked about it to Boogie at some point, but that fell through).
It's absolutely not the Maddox V2 he wanted. At this point, the lolsuit is such ancient history that Maddox would unironically be a better person to associate with than Vito the Pedo. I talked about this a few pages back, but I guess to Dick's credit he feels he needs a token liberal voice to balance out his views and not just make it an echo chamber. It's just that he's burned so many bridges and is so stubborn in listening to advice about not surrounding yourself with retards thar the people he has to have on his show are completely loathsome attention whores like him and Digibro and Mr. Girl and Riley.