Jaybo

Jaybo is a friend of Tony and step-son of Cadillac Joe, a personal friend of Tony who passed away and is revered by Tony. Jaybo, also known as KalKwen, was Tony's producer for a while, and made things interesting.

Jaybo knows that the show needs entertainment, and so has not restricted emails and callers to the extent that Tony prefers. Additionally, he has pressured Tony into letting the callers have fun and not be a tyrant who shuts down everyone a la Ghost.

Outside the show
In real life, Jaybo is an MMA fighter and amateur wrestler. Whenever Tony attended his matches, Jaybo would point to him and call him fat. One time he wiped the sweat off his forehead and flung it at Tony. Since then Tony has refused to attend any more matches.

As well as being a friend and supporter of Tony, he is also a troll. One time Jaybo doctored a diaper with Nutella and peanut butter and left it on the roof of Tony's car. He then licked the 'shit', which made Tony vomit.

It has also been theorized that Jaybo was the one who has been supplying Jesco and Sully with tales of Tony, such as being refused access to sit on a horse, singing at clubs dressed as Prince and Michael Jackson, and for allegedly stinking up the bathroom in a restaurant and getting thrown out.

JayboTalk
A couple of times Tony let Jaybo has his own shows: JayboTalk. Things turned south when Jaybo pretended not to hear Tony when he called in, despite DCII backing up Jaybo about the technical issues.

Jaybo's stunt on JayboTalk saw him fired as producer. Like an abused wife Tony has kept Jaybo around. As Jaybo and Don are good friends, they often corroborate on shared experiences, such as the craziness of BBF's funeral.

Whenever Tony ragequits a show too soon, such as the infamous 2019 DCII birthday show, Jaybo would host a show on TonyTalk to make it up to the fans. Jaybo and friends called up Joseph Gibson's show to congratulate him on winning the 2019 Dick Suck Awards. What transpired were plenty of shit-talk.