Maybe Fred knew something about Rolla we didn't know. In the episode " 'Ol Brown Eye", Fred was taken to police station for admitting that he stole Sinatra's signature ring. Lamont and Rolla went down to station to see what's going on. As they were walking pass the holding cells in the station, one of inmates recognize Rolla and called out to him.

So when Fred told Lamont that in order to get in contact with Rolla' friends is to contact the warden, he might have been right :D

https://i.pinimg.com/736x/20/ad/61/20ad61d22a88d17f5804c4955d17bf6a.jpg

Or that it was a Ongoing Mystery about Rollo's personal life that the writers decided to never reveal for some odd reason. It hinted at the fact that he has a criminal background but never explained for what

In all fairness to Rollo I’ve had friends in jail. Some I’ve known since kindergarten. Doesn’t necessarily mean I’m a criminal just because I know people who are in jail.

In all fairness to Rollo I’ve had friends in jail. Some I’ve known since kindergarten. Doesn’t necessarily mean I’m a criminal just because I know people who are in jail.

True. But there were several moments during the series that hinted that Rollo had a criminal past

True. But there were several moments during the series that hinted that Rollo had a criminal past

One of the hint might have been that he sometimes wore very fancy clothes with a wide rim hat on the show. Like SweetDaddy wore on the Goodtimes :D

One of the hint might have been that he sometimes wore very fancy clothes with a wide rim hat on the show. Like SweetDaddy wore on the Goodtimes :D

He was more connected to a Pimp than a criminal

In the "Have Gun, Will Sell" episode when they are deciding who will take the gun into the pawn show, Rollo says he can't do it because all the pawn show owners know him and will probably call the police if they see him. I think this implies that Rollo has probably been caught attempting to pawn stolen items before.

In the "Have Gun, Will Sell" episode when they are deciding who will take the gun into the pawn show, Rollo says he can't do it because all the pawn show owners know him and will probably call the police if they see him. I think this implies that Rollo has probably been caught attempting to pawn stolen items before.

In that episode he also told Lamont that if he walk into pawn shop with a stolen gun, the police will charge him with every murders on the book since Lincoln :D