Well, that's the beauty of it. If the bet is properly bankrolled, Matt pays out, and his name doesn't take any hit, other than "Hehe, remember that time Matt bet that Pirate wasn't a Ponzi? What a goof."

I want to be clear here: This is NOT an accusation. I don't think this is what's happening. I hope it's not, in fact. But damn, is it a plausible explanation.