The Las Vegas comedian Vinnie Favorito illustrates this syndrome. A famed insult comic, his once thriving career is now in jeopardy because of litigation over numerous unpaid loans. While people can get into debt over no fault of their own in some cases, it usually has a lot to do with their egocentric impulsiveness.
Insult comics are certainly not getting laughs by making the audience warm to them. The humor comes from the cruelty being inflicted on audience members. It's a highly dominant, aggressive performance mode. Reports that Favorito seems to have pressured several individuals into loaning him money without paying it back is hardly surprising.
This was certainly not the case with Bill Cosby, who seems to be the exception that proves the rule. His warm avuncular presence on stage and screen jars hugely with the revelation that he's long been a serial sex predator. Obviously he wasn't going to reveal that side of himself for laughs. And it looks very much like his persona has been concocted in part to cover it up!