Since this guy was used to conning people, he had to be conned for him to know that it was not a good thing. Mistress Van Licks and her friends got together and they dominated him financially and spent his money as he watched. He was humiliated as they cleaned him out. He never tried to con people again as he knew that he would be held responsible for it.
This guy was a spy. He had been paid to mine for information from mistress Van Licks, lady Adora and lady BlackDiamoond. But the mistresses were smarter than he thought and they realized what he was doing. They laid a trap for him and when they caught him, he was debriefed and after they got all the info they wanted, he was forced to pay them for their troubles and he did.