Look at the dates he paid out the league last year, I remember a certain someone who came into some cash right about then. It looks like he's progressively getting bigger & bigger leagues together like druff said to set up the long con. He was also involved in the NWP community & the spin offs & seemed to be changing screen names every so often as people caught onto & could prove his small scams.
Could this be Jasep? I'd almost bet it is.
He seemed to rub some the wrong way because they knew that Jasep account was up to something but couldn't quite connect the dots until the end. Are the dots starting to get connected over on 4, maybe a little earlier than he anticipated? Most of his responses sure sound like something a serial scammer would say, right from the avoid answering the questions right down to the threatening a (lol) lawsuit.
Last I knew Jasep was in the Boston area(Connecticut is close enough) so this also fits in to this guy's known history.