You begin by offering some sympathy to the man for his losses, noting that you lost your parents to illness as well. He nods his head and mumbles some words of thanks, but clearly does not want to linger on the subject.
Sensing his mood, you offer him congratulations on what he has done here in Pigsend, bringing a group together like that. You reflect on your own beginnings in Feroshire, and praising his leadership skills.
"I'd say thank you, but I'm not sure what I've really done here. People mostly keep themselves in line. I solve a few disagreements, true, but anyone with an ounce of sense could do so."
Deciding to take a different approach, you ask him why people call him the Bandit King. He cracks a smile, finally. "Probably has as much sense to it as people calling you the Peasant Count. A few months back, we were being harassed by a group of bandits. I approached them and offered to give them a place to live and work in safety. Most of them took me up on the offer. Some are in the militia now, but most of them just wanted to get back to farming. So... apparently that makes me the King of the Bandits. I don't discourage it because it seems to keep people from interfering with our business, for the most part."
You compliment him on his cleverness, and again offer praise for his wise leadership of his village. You segue into a tale about how what he's built is under threat by the Sea Raiders, who are encroaching heavily on your people's lands. He listens to your tale of demon worship and national peril with mild interest, and when your done, he plays with the end of his mustache for a moment.
"So I imagine you're here to get my help with this? What can I offer? Despite my talk of militia, we only have about thirty lads who are any good with a bow, and none of them are real fighters like those men in the alley. Were you hoping that I'd have a fearsome army of bandits, Sam Stone? Perhaps this is one case where my name has done me a disservice, then."